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The Best Day Trips in Tuscany for a Wine-filled Adventure With Stunning Scenery

No matter which route you choose, you can expect delicious food, wine, and superb views.

Whether coastal or country, Tuscany is made for four wheels. The roads caress every dip and curve of the hilly, pastoral landscape and are banked like a racetrack at every turn. The smaller strade provinciali (country roads) rarely see traffic, and each one offers an enticing scene dreamier than the last: hilltop castles, ancient farmhouses, vineyards , fields of poppies and lavender, and more. It's worth investing in a great rental, like a vintage Fiat Spider convertible, though a Fiat 124 or souped-up SUV will do. And since this is Tuscany, you'll want to make time to take in the drive with picture-perfect pit stops. Without further ado, read on for some of the best day trips in Tuscany, and plan your route.

A Tuscan Fairy Tale

Val d'Orcia is arguably the most visually impressive and romantic area of Tuscany. Listed as a UNESCO World Heritage site in 2004, the lush landscape of hill towns and rolling greens is the setting for a fairy tale. Starting in Pienza, travel south and then east to Monticchiello, a perfectly preserved 15th-century village. Continue on the serpentine route south for 30 minutes to Radicofani, another medieval town with a gorgeous fortress tower. Enjoy lunch at La Grotta , then head northwest to Bagni San Filippo to soak in the natural thermal baths. You'll be relaxed on your half-hour drive to Castiglione d'Orcia, where you can take in the Val d'Orcia landscape from the town tower. Then, it's on to San Quirico d'Orcia for more medieval Tuscany and great views. From here, you'll fall in love with a trail of towns: Take the old SP137 road northwest for 10 minutes to Torrenieri, then go northeast on SP14, a gorgeous ridge road that leads to Montisi. (Make sure to stop at San Giovanni d'Asso along the way). Meander the SP71 road south to Petroio and walk its corkscrew streets. On your way south to Montepulciano, stop in Montefollonico. Tip: You might want to break up the drive into a few days. Every town mentioned is perfect for an overnighter.

The Wine Route

Wine lovers who love a great drive, welcome to Brunello country. From Montalcino, it's a short 10-minute drive south to Castelnuovo dell'Abate, where you can visit the radiant travertine and alabaster church of Sant'Antimo and be enchanted by the haunting Gregorian chants at daily mass. About five minutes down the hill is Poggio di Sotto for an excellent Brunello experience. Or, check out Podere le Ripi , whose bonsai wines and farm-to-table Tuscan Garden Experience are a must. Get back in the car for a half-hour drive south to explore three equally delicious medieval hill towns: Seggiano, Castel del Piano, and Arcidosso, where you can have lunch at La Tagliola , a tiny restaurant with a menu dedicated to porcini mushrooms. Then, snake your way northeast on a lazy 30-minute drive, hopscotching from Monticello Amiata to Cinigiano to Porrona. For another taste of Brunello, break at Fonterenza , and then it's back to Montalcino just in time to catch the sunset.

Art With a Side of Vino in Chianti

What's better than a trip filled with art? A trip filled with art, great food, and delicious wine. Luckily, the Chianti countryside offers it all. From Florence, take the winding road to Antinori nel Chianti Classico in Bargino. With six centuries of wine production under its belt, Antinori is one of the most historic aziende (companies). It put Chianti Classico on the map and then redefined itself with an entirely new design — an architectural undulation that blends with the hills. Speaking of blends, the wines here are excellent (a tasting is a must), and the architecture is worthy of your Instagram feed. But you're here for Antinori Art Project , an ongoing and ever-growing collection of contemporary art installations, including pieces by Tomas Saraceno, Rosa Barba, and Jorge Peris. Hungry? Antinori has a rooftop restaurant — Rinuccio 1180 — overlooking the vineyards. If not, get back in the car and buckle up for a 50-minute ride south on some of Tuscany's prettiest strade provinciali to Castello di Ama . Installations by artists like Daniel Buren, Michelangelo Pistoletto, and Anish Kapoor can be seen throughout the winery and vineyards. You're also as likely to unknowingly walk across a Pascale Marthine Tayou as you are to stumble across a Louise Bourgeois.

Going Coastal

If you prefer the beach to hill towns, head to Bassa Maremma, about 25,000 acres of coastal paradise from Castiglione della Pescaia to Capalbio. Beyond the beautiful views, there's plenty to do here, too. Parco della Maremma is a 25-kilometer nature reserve with marshlands, pinewood forests, and pastures. Walk, run, hike, bird-watch, or simply enjoy the dunes. Further south lies Talamone, a picture-perfect medieval town on a wild promontory with a castle. Just south of the town, the natural landscape forms a baia (bay) perfect for wind sports, making Talmone Italy's top destination for kite and windsurfing. Or, drive 15 minutes south to Laguna di Orbetello , the most important lagoon in the Tyrrhenian Sea — it's a major migration stopover for thousands of birds and a World Wildlife Fund site. You can explore the oasis via trail and guided tours. For something a little offbeat, another 20-minute drive south and just five minutes inland will bring you to Il Giardino dei Tarocchi , a colorful, larger-than-life art installation from artist Niki de Saint Phalle in the middle of the Capalbio countryside. Not quite your speed? Slow down and drive back north (about 45 minutes) to Alberese, where you'll meet butteri (true Tuscan cowboys) at Il Bivacco , Italy's original Wild West show.

Amalfi Coast Travel Guide | Know Before You Go | Travel + Leisure

Island adventure.

Island lovers, take note: Tuscany has some of the most beautiful, wild, and elegant islands in Italy. Driving north or south on the E80, take the Orbetello Scalo exit. Not quite an island, and more like a land strip, Orbetello is a historic town oozing with charm from the moment you pass through the imposing Porta Nuova. Ancient walls, medieval ramparts, Renaissance-era fortifications, tiny streets, and charming boutiques make Orbetello the perfect spot for a stroll. From there, hop in the car and cross an artificial causeway to Monte Argentario, heading straight to the top for the lookout at Punta Telegraph. On a clear day, you can see Giglio, Montecristo, Elba, and Corsica, if you're lucky. On a rainy day, you'll be caught up in Monte Argentario's incredible nature. Take a hike around Capo d'Uomo or grab a bite to eat at Ristoro La Sorgente , a rustic eatery serving local delights underneath flourishing pines. Then, head down the mountain for a spectacular 30-minute coastal drive southeast to Porto Ercole, a tiny fishing village that's best known as an escape for the rich and famous, thanks to Hotel Il Pellicano . Fun fact: Porto Ercole is often considered to be Caravaggio's final resting place, though art historians still have this up for debate. Get back in the car, and drive north to the seaport town of Porto Santo Stefano, where the world's most beautiful yachts and sailboats are moored. You'll want to walk around the town and enjoy the pebbly beaches. Antsy? Park your car at the port (10 to 15 euro daily) and hop the traghetto (ferry) from Porto Santo Stefano to Giglio, 21 square kilometers of dunes, cliffs, and bays You can return to Porto Santo Stefano for a sundowner.

Wild Tuscany

Southern Tuscany is wild. Divided from the north by Monte Amiata, the rugged countryside has been almost untouched for centuries. Expect original country charm, amazing food, solitude, and vast vistas. From Montalcino, head toward Sant'Angelo in Colle and pass through Sant'Angelo Scalo for a side trip to Castello Banfi and its museum. Then, make your way to the medieval fortress town of Roccalbegna, which boasts a dramatic location at the foothills of a granite monolith. Have lunch at La Pietra , a family-run locanda that has wowed guests with homemade pasta and locally sourced produce and vegetables for six generations. Continue on to Cana, a medieval town that spans the lengthy crest of a hill, and take in its ancient military fortifications. Next, it's time for Stribugliano and the great views from Castiglioncello Bandini. For a wine break, visit the vineyards of Fonterenza (more Brunello), then end the day on the hill at Sant'Angelo in Colle for a stunning sunset.

Le Crete Senesi

Stark and haunting, Le Crete Senesi is a vast area in southeast Siena spanning to Arezzo. The landscape of lush rolling hills is at once dramatic and breathtaking. Take an adventurous 45-minute drive southeast from Siena via Taverne d'Arbia to Asciano and explore the town and 11th-century Basilica di Sant'Agata, which was constructed in beautiful travertine. From here, head south on SP451 to Chiusure for a glass of wine at Locanda Paradiso, a local hangout, and gaze at the endless hills. A short drive south on SP9 and you'll arrive in San Giovanni d'Asso, complete with a magical Romanesque church. Then, it's a 30-minute roundabout drive to Abbazia di Monte Oliveto Maggiore, a 14th-century Benedictine abbey with gorgeous library frescoes and glazed terra-cotta. Finally, head back to Asciano on the SP60 road. Stop when you're ready to take in the Val d'Asso and watch the sunset.

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Home » Travel Guides » Italy » 15 Best Day Trips from Tuscany

15 Best Day Trips from Tuscany

Tuscany is a very popular region for tourists to Italy thanks to its diverse range of activities and sights.

From vineyards and culinary attractions to classic art and ancient architecture, Tuscany is one of the most varied regions in the world for tourists.

Despite this eclectic range of attractions, it is also known for having a very laid-back lifestyle, even in the larger cities of Florence and Pisa.

Whether you are interested in the most famous attractions, or some off the beaten path sights, there are plenty of great opportunities for day trips within the region and in the surrounding areas to keep your itinerary exciting.

Here are the 15 best day trips either within Tuscany itself or within easy travelling distance from the most popular cities.

1. Florence

The largest city in the Tuscany region, Florence, is a very popular destination for tourists from across the world.

Beautiful architecture, delicious cuisine and world-class museums and art galleries make this a great city to explore as part of a day trip.

Famous attractions include the Duomo di Firenze, Ponte Vecchio and the Accademia Museum where you can look at Michelangelo’s David.

Outside of the usual attractions, Florence also has a bustling independent arts scene and the cuisine, much like the rest of Italy, is excellent.

Tuscany is famous across Italy for steak, and Florence is the perfect city to try some.

2. Montepulciano

Montepulciano is well known across the country for its wines, particularly the red wine known as Vino Nobile Di Montepulciano.

There are a number of vineyards and wineries in the town where you can indulge in some wine tasting.

A couple of them also allow you to take a look at the wine production process and try your hand at some of the processes yourself.

Aside from the wine attractions, Montepulciano has some interesting historical sites including the Piazza Grande, San Biagio church and civic museum.

There is also a 15th-century villa open to tourists just a short drive from the town called La Foce.

3. San Gimignano

Located in the heart of the beautiful Tuscan countryside, San Gimignano has a lot of authentic Italian charm and oozes history.

The town traces its origins back to the medieval era, and the ancient walls of the original town are still standing to this day.

There are a few medieval towers scattered across the town, with the largest being Torre Grossa.

You can also check out some art galleries: Collegiata Duomo is the best for religious art, and Pinacoteca Civica is great for smaller, more contemporary pieces.

If you want to learn more about Italy’s medieval history, San Gimignano1300 is your best option in Tuscany.

4. Reggello

Located in the Chianti wine region, Reggello is another excellent place to sample local Italian wine and learn more about the production processes.

The town is also famous for producing extra virgin olive oil, and you can take tours of some of the farms and distilleries in the surrounding area.

The town itself has some interesting architecture, including the Abbey of Vallombrosa.

The abbey still functions as a monastery to this day, after being established in the 11th century.

The forest surrounding the abbey is also well worth exploring.

You can also learn about stone cutting in the town at Sottili’s Stone Cutting Workshop.

Another very famous city in Tuscany, Pisa is the most well-known internationally for the Leaning Tower of Pisa.

The history around why the tower leans and efforts to make sure it does not fall down is interesting, but the town also has a lot more to offer travellers visiting on a day trip.

The city centre is located a ten-minute walk away from the tower but has some very charming streets and great restaurants serving famous Tuscan steaks.

The Museo Di San Matteo contains the best collection of Tuscan artworks in the region, and the Tuttomundo is a large mural of Pisa painted by Keith Haring as an homage to the city’s beauty.

Carrara is the site of the famous Carrara Marble Quarries.

The area has a 2,000-year history of providing marble for Italy, and you can still check out functional quarries to this day.

You can listen to the fascinating history of the region from one of the many licensed tours that are run in the area, as well as witness some of the best-hidden viewpoints in the country.

Afterwards, visit a restaurant in one of the nearby villages to try Lardo di Colonnata.

This salami-like meat is produced using marble slabs from Carrara.

7. Cinque Terre

Cinque Terre is a collection of five villages along the Italian Riviera which have seen massive increases in tourism over the past decade.

It is easy to see why, thanks to the charming streets of the villages and the outstanding views over the Mediterranean Sea.

The five villages each have their own unique characteristics for different experiences as part of your day trip – from food and coffee to swimming in the sea.

The nearby town of La Spezia is also packed with historic UNESCO world heritage sites from a variety of eras.

Siena, like much of Tuscany, is packed with art and history and will provide a unique day trip that will give you a great insight into typical Italian culture.

The city dates back to the Middle Ages and is packed with old architecture and quaint streets.

Piazza Del Campo is located in the centre of the city and, shaped like a shell, is one of the most famous piazzas in the country.

You can also take a look at the famous frescos of Palazzo Pubblico, visit Etruscan tombs and try your hand at traditional Tuscan cooking with some of the many classes on offer.

Wish you could check out the canals of Venice but don’t have the time? Livorno’s Quartiere La Venezia is named after the city because of its network of canals that locals say are reminiscent of Venice itself.

There are also plenty of canal-side bars and restaurants for you to enjoy local coffee, beer and wine.

The Piazza Della Repubblica is the center point of the area and features the Dominican Church.

There are also some natural Italian spas on the outskirts of the town if you want to take some time to unwind after exploring the canals of Livorno.

Lucca is an ancient city that is older than the Roman Empire, dating back to the Etruscan period.

Lucca is like an open-air museum for some of Europe’s most well known architectural styles: from Roman to Gothic to Renaissance, this is a wonderland for architecture lovers.

You can still visit the city walls which were built in 1650 when it was an independent city-state.

Lucca is also a popular city for glasswork and jewellery design, and you can take short courses on both of these crafts while visiting the city, even if just as part of a day trip.

11. Bologna

Being the food capital of Italy, Bologna is a brilliant place to experience some of the best cuisine the country has to offer.

The world-famous Spaghetti Bolognesa is of course from Bologna, and you will notice it has a much meatier flavour than foreign equivalents.

It is also a popular student city, with the oldest university in the world, so has a very youthful atmosphere and plenty of bars to experience alongside the restaurants.

Bologna is not as well known with international visitors so most tourists will be Italian, making it a much more authentic city than some of Italy’s bigger hits.

12. San Marino

Want to tick off another country while in Italy? San Marino is the third smallest country in the world, is located entirely within Italy and is easily accessible from Tuscany.

Claiming to be the oldest nation in the world, San Marino was founded in 301AD and is filled with charming, ancient streets.

Located on top of a hill, San Marino also provides gorgeous views of the Marche region, and towards the Tyrrhenian Sea.

The capital city has been granted UNESCO World Heritage Status, and the surrounding villages provide an interesting insight into how the small country functions.

Due to being outside of the EU, consumer goods can also be bought slightly cheaper in the country.

Cecina is a small region near Livorno where you can visit ruins from the Neolithic period.

The most famous ruins are in the village of San Vincenzino, and there is a museum dedicated to the archeological finds from the area at Guerrazzi Civic Archaeological Museum.

Cecina also contains some beautiful, seemingly endless beaches which are untouched by the main tourist routes and have a much more secluded feel than other Italian beaches.

You can also discover some native Italian wildlife in the shrub areas next to the beaches, including wild rabbits, foxes and porcupines.

The best place to find all this is the Tomboli Biogenetic Nature Reserve in the village of Cecina itself.

Located just past Cinque Terre on the Italian Riviera coast, Genoa is a beautiful city that is often overlooked by tourists, making it a great place to experience a slower and more authentic lifestyle.

The city is filled with cute alleyways and ancient streets, as well as some great seafood restaurants and hidden gem-style bars.

One of the largest aquariums in Europe is located in Genoa, and you can also try out some diving with the boat tours which leave from the port.

The brightly colored streets are also known as the birthplace of Christopher Columbus, and the seafaring culture of the city is still very apparent to this day.

15. Lago Trasimeno

Another beautiful location off the regular tourist trail, Lake Trasimeno, is Italy’s largest lake outside of the Alps.

Despite being unknown to most international tourists, Italians often flock to the region during the summer to enjoy the relaxed pace of life and beautiful views over the lake.

The surrounding villages can be an interesting experience of rural Italian culture.

You can visit the medieval walls of Passignano, the Etruscan architecture of Panicale or the leaning tower of Vernazzano, which actually leans at a greater angle than Italy’s more famous leaning tower.

The lake itself is quite shallow and great for bathing in during the summer.

15 Best Day Trips from Tuscany:

• Montepulciano
• San Gimignano
• Cinque Terre
• Lago Trasimeno

21 Best Towns in Tuscany + 7 Unique Day Trips (2023 Guide)

Looking for the best towns in Tuscany?

Oh Tuscany, the land of picturesque green rolling hills, paths lined with olive trees, vineyards as far as the eye can see, and charming Tuscan villages. We have enjoyed spending time exploring the best towns in Tuscany with our kids on two separate occasions.  This time, we ventured for 3 months around Tuscany, Italy while our kids attend a world school in Pistoia (a lesser-known city in Tuscany).  

Per usual, we love to journey out by car or train, exploring not only the well-known Tuscany sites but also the small towns in Tuscany—the ones that don’t always make the main lists of Best Towns in Tuscany !  

Here, you’ll find some new ideas for day trips in Tuscany and just outside of Tuscany.

Our content is reader supported, meaning that at no additional cost to you, we may receive a commission if you click through and make a purchase from some of our links. For more information, read our disclosure here .

Traveling Throughout Tuscany Tips

Note that some towns in Tuscany are quite easily reached by train, while others really do require renting a car or hiring transportation.  Hiring drivers in Tuscany is not cheap and if you are planning to rent a car during high season, make sure to reserve one ahead of time.

💡 TIP: If you don’t know how to drive a Manual, make sure you check that your rental car location has Automatic cars!

BEFORE YOU GO :  Download the App:  TrainLine

This lets you book your train travel from your phone!  While most of the time you can just walk up and purchase a ticket, there are times when the line is long. Also, note that during the high season or holidays, you’ll want to book your important train tickets in advance . 

Ready to Plan? Check out these Travel Resources!

Safety Wing has been our go-to for trip insurance over the last few years. They are affordable and it’s easy to receive a quick quote.

Booking.com is the platform we use most often for booking accommodations!

Best Towns in Tuscany to Visit

Not only will you find a list of the best towns in Tuscany, but you’ll also find other great day trips and experiences for your vacation.

If you plan to stay overnight in any of these towns, I usually start with booking.com to seek out the best accommodations in Italy.

I recommend basing yourself somewhere and taking day trips from there.  Anything around Florence is quite central. Although Florence is increasingly more and more crowded so if it were me, I’d choose a less crowded town.  

We loved being based in Pistoia . This small city is less crowded and has easy train access. We also rented a car from the Hertz location in town. Just note that the car rental locations in the smaller towns aren’t typically open on the weekends. 

THINGS TO KNOW BEFORE DRIVING IN ITALY

👉 There are lots of toll roads in Italy. You can pay for tolls by credit card.

👉 There are camera speeding traps all over. Signs are placed so you’ll know they are present. Another indication is when traffic slows down.

👉 Most cars are manual. So if you need an automatic car, reserve it ahead of time to make sure there is one available.

👉 Most of the beautiful towns in Tuscany have a historic center in which rental cars are NOT allowed to drive.

👉 Parking can be tricky. Usually on the outskirts of town, there are free parking spots or paid parking lots.

Now onto the list of the best towns in Tuscany to help you plan your incredible trip to Italy!

1. Montecatini AND Montecatini Alto

Located between Florence and the beaches is the charming town of Montecatini Terme with enticing thermal pools and a pretty promenade. 

Plus, you get a bonus by being able to explore the cool medieval town, located on Montecatini Alto on the hilltop of Montecatini.

Montecatini Alto is the supersmall but scenic village on top of the mountain. There is a main piazza with restaurants to choose from and gelato for good measure. We ate a nice lunch and enjoyed the sunny piazza before wandering around to explore more.

💡 NOTE:   Most of the lunch places don’t start serving food before 12:00, however, there are a couple of spots that serve an early lunch!

There is a church at one end of town and a clock tower at the other.  Both sides of the skinny village hold gorgeous panoramic vistas of the Tuscan hills and valleys below. 

We really enjoyed our short trip there and would recommend it for a half-day excursion. Montecatini Terme is also nice to walk through the pedestrian zone of shops and cafes!

How to Get to Montecatini

Train:  Easy train trip !  

There are 2 train stops for Montecatini, you can take either.

We chose the 2nd (“Montecatini Centro”) but were penalized with a 10-minute wait while another train had to pass by. We have since realized that this happens regularly, so if you are coming from Florence, it may be worth getting off at the first stop “Montecatini Terme”.

If you are coming from Viareggio, get off at Montecatini Centro.

Things to Do in Montecatini & Montecatini Alto

✔️ Ride the Funicular Train

Our mission was to ride the funicular, so we charted a walk straight through the main promenade to get to the funicular train station (~15-20 minute stroll). 

Even though the scheduled times for this inclined train are every 30 minutes, the funicular leaves whenever it feels full or when they feel like it.

The cost to ride Montecatini Alto Funicular is €7.50 roundtrip per adult and €4 for kids 6-10yo.  

THINGS TO NOTE

👉 There is a free 1 stall bathroom at the station.

👉 The funicular train in Montecatini takes a break from 1:00-2:30 (13:00 – 14:30). Yes, the funicular has a siesta too so plan accordingly!

👉 Grab a front or back (outdoor!) standing spot on the Funicular Train for the best views. The ride up is smooth and the view opens up as you approach the top station. 

✔️ Take a Hike

You can also opt to walk down from Montecatini Alto to Montecatini if you want to skip the Funicular ride both ways. 

And if you’re heading back down to Montecatini, you can meander through the pedestrian zone of shops and cafes.

✔️ Relax at a Thermal Spa

You can also choose to spend the afternoon at the Thermal Spa. Terme Tettuccio is one of the main thermal spas with absolutely gorgeous architecture and grounds.

Where to Stay in Montecatini

We didn’t stay in Montecatini, as we were based in nearby Pistoia. However, there were some beautiful hotels (mansion style) and B&B that you can check out if you want to base yourself in Montecatini.

I recommend booking your accommodation in advance on Booking.com .

As one of the Tuscan towns with the most tour groups parading through, it is crucial to plan wisely for your visit to Siena.

How to Get to Siena

Recommended Car Trip.  A popular tourist town!

The location makes it not a direct nor short train trip from where we were staying in Pistoia, so we rented a car on a weekday to make a day trip out of it. 

Note that most of the roads to Siena are toll roads and paying by credit card is easiest!

Parking in Siena

We pulled in straight to a parking garage (Parcheggio Santa Caterina at €2/hour). It’s strategically located near the public escalators that cleverly and kindly coast you up to the hilltop town. This is especially nice for those with mobility issues.

Things to Do in Siena

There are 3 main attractions for us:

✔️ The heavily adorned Santa Maria della Scala cathedral .

✔️ The sprawling Piazza del Campo where the Palio di Siena horse race takes place in July and August.

✔️ The gently winding street of shops for eats and treats of Via di Citta .

Tips for Visiting Siena

👉 Arrive as early as possible to beat the tour buses. 👉 There are many tourist-catering restaurants on the piazza to sit for a meal and imagine the jockeys careening the horses around each corner of the piazza. 👉 When leaving the parking garage there is a pay station up top to slide in your ticket to pay, you then have 15m to exit.

💡 FUN FACT : The symbol of Siena is the she-wolf nursing Romulus and Remus

Where to Stay in Siena

I would recommend checking out Booking.com for the best hotels to meet your budget!

3. San Marino – A country within Italy!

Okay, okay, it’s not exactly a town in Tuscany, but it is A COUNTRY within Italy that isn’t the Vatican!

You can check another country off your list with a visit to this tiny nation completely surrounded and landlocked by Italy.

Located towards the east coast town of Rimini, this city-state has been independent since the early 300s. It’s not accessible by train, so a rental car is your best bet to get you to this medieval hilltop city center.

This fifth-smallest country in the world, San Marino has the oldest constitutional republic in the world dating back to 1600. If you stay long enough you may be eligible to be head of state. Every six months 2 captains regents from opposite parties are elected to share this post. 

How to Get to San Marino

By car is definitely the easiest, as it is about a 3-hour car ride from Florence.

Parking in San Marino

We had plans to park in a lot near the top gate, but on a Saturday there were police directing/forcing tourists to park in a lower lot. It’s actually quite nice that they had police directing instead of a bunch of tourists not knowing where to go!

Things to Do in San Marino

Here are some fun things to do while visiting San Marino.

✔️ Ride a Tourist Train/Bus: Fun for Kids!

This worked out just fine as there was a cute tourist train/bus outside the garage that rode us up to the top for 3 euro per adult and big kids. 

💡 NOTE:   There is also a cable car from a lower spot we hadn’t known about which looked to be a splendid way to transport you up.

But there were no parking spots for it by the time we got there. I’d vote to try this route if you have the option to.

✔️ Stroll Through the City and Castles

The castle walls and city center are quite charming with a pedestrian promenade of shops and restaurants to wander up and down the stone streets. The castle towers have an entry fee, but a package deal allows entry into all of them. 

We scored a rainy day, so we opted to not pay for the outdoor castle grounds entry fee and instead explored the shops. We then had lunch until the raindrops were held so we could admire the panoramic vistas and hike the castle walls that are publicly accessible, which occupied us for the afternoon.  

We had other plans, but imagine it would be an amazing sunset and/or sunrise if you have the chance to stay in the evening or overnight. The city is perched on a super high hill which is really impressive to see coming or going. 

💡 FUN FACT:   Apparently, because of its strategic hard-to-reach hilltop location, Napoleon declared he would not conquer San Marino, one of the many reasons the country still exists today.

✔️ Walk Down the Hill

We chose to walk back to the parking garage instead of paying for the tourist train back. We meandered down a twisting series of streets lined with shops, a very relaxing and peaceful stroll down the hill. 

✔️ Explore Unique Museums

If you love museums, especially weird unique museums, San Marino is known for its variety of interesting museums that you can check out all over the town/country!

Overall it is definitely lengthy for a day trip, but exciting to visit another country!  Plus, it was really fun walking along the high castle walls and skipping in and out of the shops.

Where to Stay in San Marino

Check out Booking.com for the best hotels to meet your budget. We suggest staying in the old town to be able to walk to all the cute shops and cafes.

4. Pennabilli

Since we mentioned San Marino as a fun Day Trip from Tuscany, we need to mention this small village of Pennabilli, which makes a perfect stop on the way to or from San Marino from Tuscany.  

This is definitely off the tourist route and you’ll need a car to get to Pennabilli . But it’s worth it and here is why.

We chose the slow scenic route back from San Marino and this little quaint town of Pennabilli was less than an hour away.

The only reason we knew to find this gentle gem was because of a podcast episode that proves you can find love late in life; you can show up for your partner no matter the distance; you can find purpose after loss; and you can find the sounds of silence if you roam around Italy long enough.

If you are a fan of Phoebe Judge (narrator) or just a fan of love, give this a listen here .

How to Get to Pennabilli

Get there by car. It’s just under 1 hour from San Marino and 2.5 to 3 hours from Florence.

Parking in Pennabilli is easy and free just off the historic center. 

Things to Do in Pennabilli

✔️ Explore the Main Piazza

This small Italian village proved true to be a quiet one with no fanfare and easy access to explore away. The principal piazza has a friendly fountain, a cherished church, a poppin’ pizza place, and gooey gelato—basically the core ingredients of an Italian village and everything you actually need in life.

As we wandered betwixt the alleys up and down we kept uncovering hidden wonders just beneath the surface. 

✔️ Connect with Nature

First, we stopped at a lookout to hold our breath to hear every single sound of the nature surrounding us. This land is calm and serene and natural and proud and unapologetic and unbothered by the faster pace of the world around it. 

✔️ Bell of Lhasa

Next, we stumbled upon the Bell of Lhasa which was commemorated by the Dalai Lama himself nearly 20 years ago. A random little piece of Tibet in Italy!

✔️ Be Amazed at the Place that Inspired the Background of Mona Lisa

THIS!!! Finally, we found the background scene of the Mona Lisa. This landscape was one of da Vinci’s fond favorites such that he included it in his masterpiece.

Yes, you can actually see the landscape from the Mona Lisa firsthand from a hilltop in Pennabilli.

As a stop along the way of our other adventures, it was a peaceful unvisited marvel that we truly enjoyed. 

✔️ BONUS: A Waterfall Stop: Cascata del Presalino

If you commit to the slow scenic route back from Pennabilli to the Florence area, be sure to catch the roadside stop-off to get wet in the waterfall of Cascata del Presalino! 

The whole drive is stunning up and down and all around this land where these 4 regions meet: Emilia-Romagna + Umbria + Marche + Toscana.

Where to Stay in Pennabilli

If you want peace and quiet and are away from lots of distractions, Pennabilli could be the quaint Italian village for you. I’d start with Booking.com to see options for accommodations in Pennabilli.

Some of the top-rated accommodations in Pennabilli include Hotel Il Duca Del Montefeltro and B&B Fonte Dei Billi .

Pistoia is located about 40 minutes outside of Florence, easily accessible by train. It’s a lesser-known town, which means it is less crowded (cue the smiles), yet has a lot of amenities of a city. 

We were based in Pistoia for 3 months at a world school called Boundless Life . During this time, we did a lot of exploring in the city, as well as the surrounding area! We travel full time, so exploring is part of our kids’ worldschool curriculum !

How to Get to Pistoia

It is easiest to take a train , which puts you right in the middle of the city and only a 10-minute flat walk to the historic center. 

You can drive, just know that like most Italian cities, there is a historic center where you can’t drive in or you will get fined. Parking can also be an issue. Although we had no issue finding parking on the outskirts of town, especially on the main street in front of the supermarket, Esselunga.

If you want to rent a car in Pistoia, you will only be able to rent a manual, as they rarely have automatics to rent. And note, that they usually close early on Saturdays and are closed on Sundays.

Things to Do in Pistoia

Below are a few things to do in Pistoia. If you are looking for a more in-depth overview of Pistoia, make sure to check out our post on all the best things in Pistoia .

✔️ Stroll through the Town

Walk through the historic center and meander in and out of shops. Stop for a coffee & croissant at Pasticceria Armando, and grab lunch at my favorite: Locanda del Capitano . There are many restaurants to choose from in Pistoia .

✔️ Visit the Street Market

On Wednesday and Saturday mornings from about 9-1 pm, vendors will the streets selling all sorts of goods, as well as produce. 

✔️ Explore the Zoo

To be honest, I’m not a huge fan of zoos. But, Pistoia has a nice zoo just outside of town.

✔️ Join a Cooking Class and Olive Oil Tasting

Set up a cooking class and olive oil tasting with the owner of Podere Macolo.

Where to Stay in Pistoia

I would absolutely stay at Palazzo 42 . It’s in the heart of town, nice rooms and friends that have stayed there have all loved it.

A popular Tuscany town that earns a spot on most lists of Tuscany’s best. And rightfully so. Lucca is known for being able to ride atop the city walls around the old town.

How to Get to Lucca

As always, you can drive. But Lucca is right on the train route so it’s much easier to catch a train since you don’t have to deal with parking.  The train takes approximately 90 minutes from Florence (Firenze).

Things to Do in Lucca

There are many things to do in Lucca. Here are some of our top picks.

✔️ Ride a Bike

When you exit the train station, there is a bike rental shop where you can rent bikes or these quad and … 

We rented this one for our family of 5 + my parents. It was an absolute blast riding along the entire city wall. For reference, in one of these 6-person bikes, you can do the city wall in an hour, although you really can’t waste much time.  

Where to Stay in Lucca

I recommend checking checking out Lucca in Villa Lucrezia or Hotel San Marco .

7. Montepulciano

Montepulciano is a medieval town that sits on top of a hill in southern Tuscany. Its beautiful location comes with an abundance of elegant palaces from the Renaissance period, ancient churches, vast vineyards, charming squares, and panoramic views of the Val d’Orcia and Val di Chiana valleys.

I recommend touring around this town on foot since it has many beautiful hidden corners on top of its popular landmarks. The town is also not too crowded although it has become a more popular tourist attraction after the movie New Moon was shot there.

How to Get to Montepulciano

You can get to Montepulciano via car, bus, or train.

How to Get to Montepulciano by Car

I recommend traveling by car to Montepulciano for convenience and better control over your time. If you’re coming from Siena, you can take the scenic route by going south through the Val d’Orcia on the SS2 to San Quirico d’Orcia. You’ll then have to take SS146 through Pienza until you reach Montepulciano.

💡 NOTE:   The town’s historic center is closed to traffic. This means you’ll have to park outside the town center unless you have a permit.

You can find several convenient parking lots on the edge of the town. They are well-marked so you can spot them with no problem. The parking fee can be about €1.20 every hour.

How to Get to Montepulciano by Train and Bus

If you prefer public transportation instead of driving, you can ride buses and trains to Montepulciano. The closest train station sits outside of the town and you will still need to ride a bus to reach Montepulciano.

There are buses that run hourly from Chiusi train station . You can catch a bus every 1 and a half hours from Siena. To reach the historic center from the bus station, you can either walk or ride the small orange bus.

💡 NOTE:   Keep in mind that the buses may not run on Sundays.

Things to Do in Montepulciano

Make sure to check out these activities in Montepulciano.

✔️ Visit a winery.

Montepulciano is not only known for its charming landscape and architecture. It’s also hailed as one of the best winemaking regions in the world . Their vino nobile is actually globally renowned. It’s a fine red wine made with grapes sourced from the local vineyards surrounding the town. 

✔️ Stroll along Piazza Grande.

This is the main square in Montepulciano and is a great location for a relaxing stroll. Within it are important buildings and historical landmarks, such as the Town Hall, Contucci Palace, and Palazzo dei Capitani del Popolo.

You can also find the Well of the Grifi and the Lions and the Cathedral of Saint Mary of the Assumption in Piazza Grande. The cathedral is in prime real estate but may not be as attractive as those in Siena and Lucca. 

✔️ Look at scenic views from the clock tower in Palazzo Comunale.

You can climb the 150 steps to the top of the clock tower and have better views of Montepulciano. If you don’t want to take the stairs, you can ride the elevator instead. Although there are still 52 steps left from the elevator stop before you reach the top.

Where to Stay in Montepulciano

It’s really nice to stay in Montepulciano so that you can experience the village without all the daytrip crowds. We ended up visiting Montepulciano in the evening, which was after all the day-trippers had left!

Some of the most highly rated options are Villa Nottola and Hotel Panoramic Montepulciano .

8. San Gimignano

San Gimignano is one of the more famous hilltowns in Tuscany and is enclosed by 13th-century walls. It’s located southwest of Florence and is mostly known for its 14 medieval towers, which gained it the nickname ‘Town of Fine Towers’ .

The town also boasts a 12th-century church ( Duomo di San Gimignano ), a triangular historical square ( Piazza della Cisterna ), and masterpieces of 14th- and 15th-century Italian art, to name a few.

The famous medieval towers are originally built by patrician families who used to control the town. There were 72 of these tower houses, but only 14 have survived after wars and other catastrophes.

Climbing to one of these towers is among the best things you can do in San Gimignano. The town also has a lot of charming shops and restaurants that you can visit in between touring the various historical sights.

How to Get to San Gimignano

To get to San Gimignano, you can take the train, bus, or car. Just keep in mind that there are no train stations in San Gimignano so you’ll have to transfer from a train to a bus to reach the town.

How to Get to San Gimignano by Public Transportation

The nearest train station to San Gimignano is in Poggibonsi . So if you took the train from Florence or Siena, you’ll have to get off at Poggibonsi and take the bus 130 to San Gimignano.

If you want to skip riding the train altogether, there’s always a bus going to San Gimignano from Florence, Siena, and other nearby towns. 

➡️ From Florence , you’ll have to catch bus 131 to Poggibonsi. Once you’re in Poggibonsi, you need to transfer to the #130 bus to reach San Gimignano.

➡️ From Siena , you need to ride the 130A bus. You may need to change buses in Poggibonsi but some of these buses continue to San Gimignano directly.

One thing you need to consider if you want to take the bus is that sometimes, buses don’t arrive on time. You may even have to wait for about an hour.

How to Get to San Gimignano by Car

If you’re driving a car to San Gimignano, the following is the approximate traveling distance from nearby locations:

➡️ Florence : 60 km (1.25 hours)

➡️ Lucca : 90 km (1.5 hours)

➡️ Montalcino : 80 km (1.5 hours)

➡️ Siena : 41 km (45 minutes)

➡️ Pisa : 78 km (1.5 hours)

➡️ Volterra : 30 km (40 minutes)

Driving a car to San Gimignano can give you a much better experience. However, parking can be costly but should be worth it for the convenience of allowing you to leave whenever you want to.

The cheapest parking space is at P1 Giubileo . The rate is only €1.50 every hour and a maximum of €5.00 for an entire day. Subsequent days will be subject to a discount.

P2 Montemaggio, P3 Bagnaia Superiore , and P4 Bagnaia Inferiore have rates that start from about €2.50 per hour and €10.00 for an entire day.

💡 NOTE:   P1 is the cheapest parking area but also the farthest from the center of San Gimignano.

Things to Do in San Gimignano

Here are a few things to do in San Gimignano.

✔️ Climb the tallest tower in San Gimignano .

Torre Grossa is the highest tower in town. It’s also called fat tower by some. You can see a much better view of San Gimignano if you climb to the top of this tower.

✔️ Rent one of the 14 famous medieval towers.

Torre Salvucci Maggiore is available for tours. You can even rent it and have a remarkable place to stay as you tour the rest of San Gimignano and nearby towns in Tuscany.

✔️ Explore the historic center of San Gimignano .

There are several piazzas in the historic center of San Gimignano, which has been declared a UNESCO World Heritage Site since 1990 .

Here you’ll find several small cafes, boutique shops, and Torture Museums. Many restaurants also offer the town’s famous white wine: Vernaccia di San Gimignano .

You also wouldn’t want to miss Duomo of San Gimignano. This cathedral features frescoes that showcase the stories from both the Old and New Testaments.

✔️ Discover the famous Gelateria Dondoli .

If you love ice cream, or you simply want to know why this place is so famous, you’ll have to visit Gelateria Dondoli in Piazza della Cisterna.

This gelateria has graced a lot of news articles and attracted numerous celebrities. They won the Ice Cream Championship of 2006/2007 and 2008/2009. And their Gelato Master, Sergio Dondoli, also bagged the Master of Art and Craft award in 2016 .

Their menu includes all traditional flavors while also offering unique ones, including Dolceamaro which comes with aromatic herbs, and Champelmo which is made with pink grapefruit and sparkling wine.

✔️ Food Tours and Cooking Classes

There are some really great food tours and cooking classes in San Gimignano region. Check them out here for ideas and to book . I would also opt for an organic farm when possible!

Where to Stay in San Gimignano

Check out some of the top-rated hotels in San Gimignano, such as Hotel La Cisterna and Leon Bianco .

One of the prettiest towns in Tuscany is Cortona. It’s a small, historic town in the province of Arezzo and lies on the border between Tuscany and Umbria.

Cortona sat atop a hill (600 meters above sea level) and is enclosed with ancient stone walls dating back to the Etruscan and Roman times. It’s also known for its beautiful churches, including the Basilica di Santa Margherita , and panoramic views of Val di Chiana (Chiana Valley) and Lake Trasimeno.

Cortona is also considered the main cultural and artistic center of the Val di Chiana . And while its international fame only skyrocketed when it became the set of the movie ‘Under the Tuscan Sun,’ the town has always offered lots of amazing places and fun things to do for locals and tourists alike!

How to Get to Cortona

Depending on your budget and desired level of convenience and comfort, you can reach Cortona via train, bus, and car.

How to Get to Cortona from the Airport

If you’re going to Cortona by plane, you’ll be landing at either of the following closest airports to Cortona:

➡️ Perugia Sant’Egidio International Airport 

➡️ Florence Peretola International Airport 

➡️ Pisa International Airport  

➡️ Rome Fiumicino International Airport 

From the airport, you can then ride a taxi, bus, or train.

How to Get to Cortona by Train

You can reach Cortona by train from Rome, Florence, and Venice.

➡️ From Rome

You can pick between a slow or a fast train.

The slow train will take about 2 hours and 25 minutes before stopping at the Camucia-Cortona station.

The fast train only takes 1 hour and 45 minutes but will only stop at Terontola train station which is still 10 km from Cortona.

From the station, you’ll need to ride a taxi or a local bus .

➡️ From Venice

You can ride the fast train Freccia Rossa or Italo Train to Florence, which would take about 2 hours. And when you reach Florence, there’s a local train that will stop at Camucia-Cortona station and only takes 1 hour and 20 minutes. 

How to Get to Cortona by Bus

The Camucia-Cortona and Terontola rail stations are both connected to bus services. You will ride the bus up the hill and stop just outside the center at Piazza Garibaldi. You can also ride a bus to Cortona from nearby towns and villages in Tuscany.

How to Get to Cortona by Car

If you’re traveling from Rome or Florence, you can drive through the main highway A! Superstrada del Sole and exit at the sign “Bettolle”. You will then have to take the second exit, “Cortona San Lorenzo”.

Afterward, you just have to follow the road signs to Cortona until the hill appears in about 5 minutes. 

Things to Do in Cortona

Add these things to do in Cortona to your list while visiting this charming Tuscan town.

✔️ Visit the Museum of the Etruscan Civilization (MUSEO DELL’ACCADEMIA ETRUSCA (MAEC))

✔️ Shop along the side street of Cortona

✔️ Explore Cortona on foot through Via Nazionale 

✔️ Go sightseeing at Belvedere di Cortona

✔️ Enjoy a delicious gelato

✔️ Visit the Diocesan Museum

✔️ Visit this cute shop for a wine tasting

Where to Stay in Cortona

Definitely check out Hotel San Luca or Villa Schiatti .

10. Suvereto

If you’re looking for charming villages in Tuscany, Suvereto is another medieval town that should go on your list. 

It’s nestled in the province of Livorno, in between the hills and the Etruscan Coast. Within its walls, you can travel back in time to before 1000 as you gaze upon the prominent old architecture and stonework.

From historical buildings to medieval churches and stone houses, structures all around Suvereto create an ancient yet welcoming atmosphere.

Nature also plays a big role in this Tuscan town’s charm. Suvereto is surrounded by chestnut trees, oak trees, and cork trees (Quercus suber)—which is where the town got its name.

How to Get to Suvereto

You can reach Suvereto by bus, train, ferry, or car.

How to Get to Suvereto from the Airport

Nearby airports to Suvereto include:

➡️ Elba Island Airport

➡️ Pisa Airport

➡️ Florence Airport

➡️ Rome Airport

From the airport, you can ride a bus or train to reach Suvereto.

How to Get to Suvereto by Car

➡️ If you’re from the north , you’ll need to take the A12 Genova-Livorno-Rosignano Marittimo motorway before exiting at Rosignano Marittimo. You’ll then continue to the SS 1 highway and follow the direction for Venturina-Piombino-Elba.

Continue to follow the directions for direction for Venturina-Campiglia Marittima until you reach SS 398, which will take you up to Suvereto.

➡️ If you’re traveling from the south , take the A12 motorway to Civitavecchia then continue on the SS 1 Aurelia to Grosseto. Then follow the directions to Venturina – Piombino – Elba Island then to Campiglia Marittima before taking the SS 398 until you reach Suvereto.

Things to Do in Suvereto

✔️ Explore Museo di Arte Sacra “San Giusto” (Museum of Sacred Art of Suvereto)

✔️ See the 14th-century depiction of Madonna con Bambino at the Chiesa della Madonna di sopra la Porta.

✔️ Tour the inside of the 13th-century palace: Palazzo Comunale.

✔️ Discover the collection of dolls from various eras in the Museo della Bambola.

✔️ Get close to the Romanesque architecture of Pieve di San Giusto.

Where to Stay in Suvereto

Some of the best accommodations in Suvereto include Borgo al Cielo – Albergo Diffuso and Agriturismo Biologico Bulichella .

Barga is a charming town in northwestern Italy, located in the province of Lucca. It’s set on top of the Tuscan-Apennine hills (410 meters above sea level) right in the heart of the Serchio Valley.

Aside from being a beautiful home to around 10,000 people, Barga is also a worthwhile tourist destination. It offers a picturesque view of nature, medieval architecture, tons of outdoor activities, and a dynamic music scene.

Barga is widely recognized in the tourism industry. It bagged several awards, including “One of the Most Beautiful Villages in Italy,” and merits from “Orange Flag Touring Club” and “Cittaslow”. 

How to Get to Barga

You can reach Barga by train, bus, or car.

How to Get to Barga from the Airport

There are five airports closest to Barga:

➡️ Milan Airport

➡️ Verona Airport

➡️ Bologna Airport

From the airport, you can either ride a bus or a train to Barga.

How to Get Barga by Train

You can only ride trains heading to Barga from Lucca and Pisa Centrale stations .

There are more frequent trains from Lucca and will take you on a direct 40-50-minute ride to Barga. 

If you’re leaving from Pisa Centrale, you’ll most likely need to stop at Lucca to change trains. There are only about 5 trains every weekday that go directly to Barga from Pisa Centrale station.

How to Get to Barga by Bus

Buses to Barga mostly leave from Lucca and will take about an hour. And if you’re already in the Garfagnana area, you can catch a bus from Pieve Fosciana, Castelnuovo, and Castelvecchio.

How to Get to Barga by Car

➡️ From the South

Take Highway A1 towards A11 before heading to the Capannori exit. From there, follow indications to SS 439 towards Lucca-Borgo a Mozzano-Fornaci di Barga. You’ll then have to follow the signs to Barga on SS 445. 

➡️ From the North

Take Highway A1 following the signs to Genova-Livorno, Viareggio, and to Lucca. You’ll need to exit at Lucca est and follow the indications to Borgo a Mozzano and Fornaci di Barga before taking the SS 445 to Barga.

Things to Do in Barga

✔️ Visit the Romanesque-style Cathedral of San Cristofano.

✔️ Explore in the Museo Civico del Territorio.

✔️ Stroll along the main square of the center: Piazza del Comune

✔️ Visit and learn more about the historic Teatro dei Differenti.

✔️ Admire the 16th-century complex of Santa Elisabetta Church.

Where to Stay in Barga

For some great options to stay in Barga, check out Il Ciocco Hotels and Villa Gherardi – B&B e Hostel .

12. Monteriggioni

Monteriggioni is another one of the walled medieval towns in Tuscany with well-preserved walls, a castle, and defense towers. It lies on the hill of Monte Ala in the province of Siena, where its imposing towers have stood since the beginning of 1200.

💡 FUN FACT:   The towers are so impressive that Dante Alighieri referred to them as “horrific giants” in his Divine Comedy.

Without a doubt, Monteriggioni has retained its Medieval character, which makes for this circular town’s main charm. But aside from its historic structure, Monteriggioni is also highly regarded for its vast vineyards and several excursion destinations. 

How to Get to Monteriggioni

You can reach Monteriggioni by bus or car. Unfortunately, there are no train stations in town. The closest railway station is Castellina in Chianti-Monteriggioni, which is still 3km from Monteriggioni.

How to Get to Monteriggioni from the Airport

There are five closest airports to Monteriggioni:

➡️ Bastia Airport

➡️ Forli Airport

From the airport, you can reach Monteriggioni by riding a train. However, if you’re leaving from Pisa, you’ll have to transfer to a bus before reaching Monteriggioni.

How to Get to Monteriggioni by Bus

You can ride a bus to Monteriggioni from the nearby cities, including Florence, Pisa, and Volterra. Bus stops near the castle of Monteriggioni are the Rotonda (main bus stop) and Scuola.

Both stops are about 500 meters from the castle.

How to Get to Monteriggioni by Car

Traveling by car to Monteriggioni is the more convenient option since you’ll have control over your time. However, keep in mind that vehicles are prohibited inside the town proper . You will have to leave your car at either of the several parking lots outside of Monteriggioni.

💡 NOTE:   All parking spaces require a small fee.

You can get here by car via the Florence-Siena dual-carriageway. You need to take the “Monteriggioni” exit 10km from Siena (the city) and simply follow the directions toward the town.

Here’s the approximate distance and driving duration from several nearby destinations:

➡️ Siena – 21 km (20 minutes)

➡️ Florence – 65 km (1 hour)

➡️ San Gimignano – 28 km (50 minutes)

➡️ Volterra – 40 km (50 minutes)

Things to Do in Monteriggioni

✔️ Taste the traditional red wine of Monteriggioni: Chianti Colli Senesi Monteriggioni

✔️ Visit in July and take part in their famous Medieval Festival.

✔️ Try on some ancient armor and swing a 10kg sword at the Museo delle Armature (Museum of Arms – Monteriggioni in Arms).

✔️ Visit the tiny 13th-century Church of Santa Maria Assunta.

✔️ Enjoy great food and drinks at the heart of Monteriggione: Piazza Roma

Where to Stay in Monteriggioni

Borgo San Luigi and Il Piccolo Castello are great choices of accommodations in Monteriggioni.

13. Fosdinovo

Another small town in Tuscany that is worth visiting is Fosdinovo. It’s located in northern Tuscany just 45 miles north of Pisa. It lies within the drainage basin of Val di Magra and is considered the gateway to the historic Lunigiana region.

Although this town is not a staple in every tourist’s itinerary, I know you won’t be disappointed. It boasts a perfectly preserved castle-fortress and a scenic view of the sea and mountains.

The town is also close to the Apennine and the Apuan Alps. So contrary to the rolling hills that you can find in southern Tuscany, steep hills will meet you in Fosdinovo. Winter may also bring snow to this small village.

How to Get to Fosdinovo

You can reach Fosdinovo by train, bus, or car.

How to Get to Fosdinovo from the Airport

Included in the airports closest to Fosdinovo are Pisa Airport and Florence Airport .

From either airport, you can either ride a bus or train to go to Fosdinovo. Riding a taxi is also another option if you’re leaving from Pisa Airport.

How to Get to Fosdinovo via Public Transport

The closest railway station to Fosdinovo is Sarzana. From there, you’ll need to ride a CTT bus to reach Fosdinovo.

How to Get to Fosdinovo by Car

You’ll need to drive via the A12 motorway and take the Sarzana exit. Continue driving on the Aurelia state road towards Carrara until you reach the crossroads for Fosdinovo. You’ll then need to climb for about 6 km before you reach Fosdinovo.

Things to Do in Fosdinovo

✔️ Explore the town’s main attraction: Malaspina Castle.

✔️ Visit the marble tomb of Galeotto Malaspina in the Church of San Remigio

✔️ Admire the 15th-century wooden statue of the Virgin Mary in the Compagnia dei Bianchi Oratory

✔️ Stroll along the beautiful park in Villa Malaspina

✔️ Learn more about the resistance in the Apuan and Luni areas in the Audiovisual Museum of the 2nd World War Resistance.

Where to Stay in Fosdinovo

Both Castello Malaspina di Fosdinovo and Locanda De Banchieri are highly rated by hundreds of travelers as some of the best hotels in Fosdinovo.

14. Volterra

Volterra is a hilltop Etruscan town in Tuscany. It’s located in the province of Pisa and attracts countless tourists for its archeological sites, museums, excursion destinations, and overall picturesque landscape. 

The town’s Etruscan heritage is still evident to this day, especially with the protective walls that have surrounded the town since the 5th to 4th centuries BC.

Volterra is also filled with boutiques and handicraft workshops where you can choose from a wide range of souvenirs. Included in your choice are alabaster handmade objects for which Volterra is highly regarded.

💡 FUN FACT:   Volterra is dubbed “the city of Alabaster” for their world-famous work with Alabaster. This ancient tradition originated from the Etruscans.

Tip : Use their Volterra Card so you can save money on most entrance fees to the town’s several attractions.

How to Get to Volterra

You can reach Volterra via train, bus, or car. You also have the option of riding a taxi if you’re leaving from an airport.

How to Get to Volterra from the Airport

There are five airports near Volterra:

From there, you’ll need to ride a train before transferring to a bus or taxi. However, if you’re leaving from Bastia Airport, you’ll need to ride a ferry and then a bus (or drive) before reaching Volterra.

How to Get to Volterra by Car

Volterra is not too far from the surrounding cities and you can definitely drive there. However, you need to keep in mind that the last kilometers before reaching the town proper might be a tad difficult since the road is very curvy and goes uphill.

If you’re leaving from Florence, you need to take the Firenze-Siena roadway before taking the exit at Colle di Val d’Elsa Nord. You’ll then have to follow the road signs toward SR68 and Volterra.

How to Get to Volterra by Bus

You can take a bus to Volterra from Pisa, Siena, and Florence. However, there are no direct routes and you’ll have to change buses before getting to Volterra. 

If you’re at the Volterra Saline-Pomerance train station, take the bus line 780 which is only about a 20-minute ride to Volterra.

How to Get to Volterra by Train

The Cecina-Volterra railway line is the closest train station to Volterra. You’ll have to get off at the Volterra Saline – Pomarance stop, which is still 10km away from the city center of Volterra. However, this line is small so check the train schedules beforehand.

There are larger railway stations that are still close by as well. These are in Cecina and Pontedera.

Things to Do in Volterra

✔️ Taste some delicious Italian delicacies during Volterra’s Saturday market.

✔️ Climb the tower of Palazzo dei Priori to better enjoy the town’s view.

✔️ Stroll along and relax in the town’s main square: Piazza dei Priori

✔️ Pass through the Porta dell’Arco, the oldest gate in Volterra.

✔️ Explore the Museo Etrusco Guarnacci (Etruscan Museum)

Where to Stay in Volterra

Check out Albergo Etruria and Hotel La Locanda for your hotel stay in Voleterra!

Pienza is a small town perched on top of a beautiful hill in the province of Siena. The town offers magnificent views of Val d’Orcia, encompassing expansive vineyards, rolling hills, charming villas, and rows of cypress trees. 

Aside from its natural landscape, Pienza is also famous for its pecorino cheese, historic buildings, and romantic street names. This Renaissance town is known as a legacy of Enea Silvio Piccolomini (Pope Pius II) as well.

Pope Pius II redesigned the town to embody his idea of the ‘ideal city’ with respect to his Humanist vision and philosophy. He tasked architect Bernard Rossellino and the great humanist Leon Battista Alberti to lead the construction project.

After 3 years, they have successfully built the Piazza Centrale, Pienza Cathedral, the Papal Residence, and the Municipal Palazzo, among others. Palazzo Piccolomini is what Pope Pius II chose as his summer residence.

After the redesign, the town, which is previously called Corsignano, was renamed Pienza, which translates to ‘city of Pius’. In 1996, Pienza was officially recognized as a UNESCO World Heritage Site.

How to Get to Pienza

Depending on where you’re traveling from or your personal preferences when it comes to comfort and convenience, you can get to Pienza by car or bus. You might also have to ride a train to a nearby town and then transfer to a local bus since there is no train service in Pienza.

How to Get to Pienza by Car

Pienza is between San Quirico d’Orcia and Montepulciano on SS146. Going there by car is the easiest , in my opinion. You won’t have to rely on bus schedules which can leave you waiting for a long time.

➡️ If you’re from Montepulciano , you can take the road to Torrenieri and SS2. Then, take the SS2 south to San Quirico d’Orcia. You can then find the SS146 which runs east to Pienza.

➡️ If you’re from Siena , you need to take SS2 south to SS146. But if you prefer a more scenic route, you can take SS438 south through Asciano and via Monte Oliveto Maggiore.

➡️ If you’re from Florence , the quicker route is taking the A1 Autostrada and EXIT Valdichiana. This will only take about an hour and 40 minutes. Although this can change depending on the traffic. For a more scenic route, your option is to take the FI-SI (Raccordo Autostradale Firenze-Siena) and EXIT Siena Sud. This can add 20 more minutes to your traveling time.

➡️ If you’re from Rome , take A1 Autostrada and EXIT Chiusi-Chianciano Terme. Depending on the traffic, you can reach Pienza between 2 hours and 3.5 hours.

How to Get to Pienza by Bus

If you don’t want to drive a car, there’s always the option of taking the bus. A bus service between Chiusi train station and Montepulciano can bring you to Pienza. You can also catch a bus from Siena.

💡 NOTE:   It’s important to study the bus schedules in order to save some time waiting for a bus to arrive. Also, there’s only a limited bus service running on Sundays and public holidays.

➡️ If you’re from Florence , you’ll need to go on a bus to Siena, which could take about 3-4 hours. From Siena, you’ll have to change buses at least once to reach Pienza. 

➡️ If you’re from Rome , the entire bus ride to Pienza can take at least 5 hours. You can ride the FlixBus to Siena and then transfer to a local bus to reach Pienza.

Things to Do in Pienza

Pienza is such a small town that I would still recommend visiting it even if you only plan a short visit to Tuscany.

✔️ Visit the previous summer residence of Pope Pius II: Palazzo Piccolomini

Just beside Pienza Duomo, you can see the very walls wherein Pope Pius II resided during summer. There are guided tours for Palazzo Piccolomini that happen at regular intervals during the day. The tours come with a host and an audioguide, and usually last for about 40 minutes.

You will be guided through the different rooms inside the palace. The audio guide will then offer an explanation in your chosen language and in your own time. The tour also includes rooms that can be interesting for kids as well, such as the armor room and the Pope’s bedroom.

To culminate the tour, you will be brought to the amazing suspended garden in Palazzo Piccolomini. This will allow you to bask in the vast stunning views of the countryside. The garden’s strategic location is intentional, placing it at the heart of the vision of the Pope’s ideal town.

✔️ Taste the pecorino cheese that Pienza is famous for.

Pienza is especially proud of its pecorino cheese—and rightfully so!

This cheese is made from sheep’s milk and comes in many varieties. The two main varieties are:

🧀 Red Rind Cheese seasoned with Tomato Juice

🧀 Black Rind Cheese (aged pecorino)

If you want to try some, you can easily find pecorino cheese in the shops all over Pieanza. I recommend trying it alongside some cured meats and a glass of their local wine too! Pasta dishes are often made with the famous cheese as well. 

💡 FUN FACT:   Pienza celebrates ‘Fiera del Cacio’ in September. This is a folkloric event where local producers can test their skills at making cacio wheels roll around a wooden pole. This event is held at Pienza’s main square.

✔️ Stroll along Piazza Pio II

Piazza Pio II is the town’s main square and was named after Pope Pius II. It has a unique trapezoidal shape and is dotted with several important structures, like the cathedral, Palazzo Borgia, Palazzo Piccolomini, and an ancient well called ‘pozzo dei cani’ or dog’s well. 

You can find it relaxing to simply stroll through the square and admire the 15th-century buildings. Or if you happen to visit during summer, you might catch one or two concerts being held here.

💡 NOTE:   Piazza Pio II is car-free. So if you’re driving a car, you have to park at some of the designated parking spaces before coming here.

✔️ Visit Pienza Cathedral and explore the crypt below it 

Cattedrale dell’Assunta is Pienza’s cathedral and is located in Piazza Pio II. It was built in the 15th century by architect Bernardo Rossellino. The architecture of the building is a reflection of the Renaissance style and some Gothic influences that Pope Pius II saw and liked during his travels.

And after you’ve admired the cathedral’s structure, I recommend exploring the crypt and labyrinth below it. 

The crypt is the San Giovanni church that preserved the baptismal font designed by Bernardo Rossellino. You can see many Flemish tapestries within the crypt, as well as the medieval Santa Maria church.

A little beyond the crypt is the labyrinth: a maze of narrow brick tunnels. Visiting both the crypt and labyrinth can take between 15 and 30 minutes. But unlike in Montepulciano, there are no caves. So I only suggest visiting if you simply want to see the entirety of the cathedral and the church of Santa Maria.

💡 NOTE:   The cathedral is closed on Tuesdays and visiting hours vary depending on the day and season. It’s best to check their official website prior to visiting.

Where to Stay in Pienza

Relais Il Chiostro Di Pienza and Borgo Sant’Ambrogio – Resort are a couple of highly recommended places to stay in Pienza.

Arezzo is technically a city, not a town. But it’s always worth a visit so I wouldn’t leave it out my list.

Arezzo is known as the city of gold and high fashion . Many known artists and poets are from Arezzo, including Giorgio Vasari, Guido of Arezzo, and Guittone d’Arezzo. The Renaissance artist Michelangelo also hailed from the province of Arezzo.

The city is filled with amazing frescoes and sculptures, most of which you can find in churches. Some of the more popular artworks are the painted vaulted ceilings and the 15th-century fresco of Mary Magdalene made by Piero della Francesca in the Arezzo Cathedral. 

The Basilica di San Frances also has a chapel that is adorned with more of Piero’s stunning frescoes. And in Basilica di San Domenico , you can find the 13th-century painting ‘Crucifix’ by Cimabue. 

Aside from art and history lovers, shopping fans will also find Arezzo worth visiting. From trendy clothes and elegant jewelry to household goods and antiques, you can find all kinds of items you’ll want for a shopping spree!

How to Get to Arezzo

In order to get to Arezzo, you can either take the train, ride a bus, or drive a car. For convenience, I always opt for driving a car and suggest you do the same as well.

How to Get to Arezzo by Car

You can easily reach Arezzo by taking the Autostrada del Sole (A1 Milan-Naples). You will then take the exit at the tollgate of Arezzo and travel for about 11km more to reach the city center.

➡️ If you’re from Siena , you first need to take the SS73. This connects to Autostrada di Sole where you’ll then go north before exiting at Arezzo.

But if you want a more scenic alternative to this route, you can always take the exit at Colonna di Grillo and head toward Chianti before reaching Arezzo. Or you can take the exit at Rigomagno and stop at Lucignano before you can reach Arezzo.

How to Get to Arezzo by Train

If you don’t want to drive, traveling to Arezzo by train is also fairly easy. The train station of Arezzo is located along the Bologna-Rome railway line. Trains from Rome, Florence, and other places in Italy frequently run to Arezzo too, so you probably won’t have a very difficult time waiting.

Things to Do in Arezzo

Although Arezzo is out of the way from the more famous tourist spots in Tuscany, this charming city has so much to offer. Whether you’re a solo traveler or you have your family with you, you can find a lot of fun things to do in Arezzo.

✔️ Watch a historical reenactment

If you happen to visit Arezzo on the third Saturday of June and the first Sunday of September, I recommend watching the reenactment of the Saracen Joust held in Piazza Grande. But if your visit doesn’t coincide with these dates, you can still learn about Saracen Joust at the Saracen Jousting Museum.

✔️ Admire the beauty of the Palace of Fraternita dei Laici

This palace is a gorgeous building that you can find in Piazza Grande, the main square of Arezzo. The structure itself is already noteworthy so if you’re in a rush, you can just admire it from the outside.

It’s amazing to see the sculptures of Bernardo Rossellino (the Madonna della Misericordia) and the statues of Pope Blessed Gregory X and St. Donald placed artfully outside of the palace. You can also see one of the oldest functioning clocks in Italy on top of this building.

If you have a bit more time, I suggest going in, especially if you’re fascinated by the arts. Inside the palace is the Museum of Fraternita, which holds a vast collection of 6000 paintings, sculptures, and antique furnishings.

💡 NOTE:   There is a small entrance fee to the museum.

✔️ Go shopping!

After visiting museums and witnessing historical artworks, you can enjoy yourself more and indulge in some shopping. One good place to do this is Corso Italia, a pedestrian street that’s always bustling with activity. There are a lot of boutiques, antique shops, cafes, and restaurants on this street. 

And if you particularly want a plethora of choices when it comes to antiques and other items, I recommend visiting Arezzo on the first Sunday of every month.

During this day, the festive vibe in the city is magnified as approximately 400 stalls open up in Piazza Grande and the surrounding streets. You can find various artwork, furniture, clothing, home goods, toys, and jewelry.

Where to Stay in Arezzo

When looking for places to stay in Arezzo, check out B&B Hotel Arezzo and Hotel Minerva .

17. Pitigliano

Pitigliano is a small town in the Maremma region that was built on a tuff cliff. It’s located on a ridge about 300 meters above sea level and is surrounded by panoramic green valleys. With scenic views and rich history, Pitigliano is one of the best spots in Southern Tuscany.

💡 FUN FACT:   An ancient legend credits two Romans in the name of Petilio and Celiano for the foundation of Pitigliano. And it is by combining their names that the town got its own name.

Due to its interesting location, it became a unique-looking walled town whose main attractions include its medieval stone streets, museums, and the Jewish quarter.

Ptigliano is actually well known for its nickname ‘Little Jerusalem’ . This is because when the Jews were escaping, this town became their refuge in the 14th century. And as their number grew, they built a temple in Pitigliano in 1598.

When the 17th century came, Medici annexed Pitigliano which led to the Jews being confined in ‘ghettos.’ Fortunately, the local government understood the Jews’ vital role in the town’s economic and commercial activities and they worked on improving their status and fundamental rights.

How to Get to Pitigliano

You can get to Pitigliano by car, bus, or train. However, if you’re taking the train, you still need to transfer to a bus in order to reach Pitigliano. There is no train station within the town itself.

How to Get to Pitigliano by Car

Driving a car to get to Pitigliano (and to go around Tuscany) is the best option for me.

You need to take the A1 motorway heading to Rome and get off at Orvieto. You then need to take SS71 towards Bolsena, then SS2 Cassia, and SS74 which heads toward Pitigliano.

You have to drive through Grande Raccolto Anulare towards Florence. Once you reach Rome, take the A1 highway, turn at Orte, and follow the signs for Viterbo. You just then have to take SS71 until you reach Pitigliano.

➡️ If you’re heading in from Rome , you will have to take the Roma-Civitavecchia motorway and follow the signs for Grosseto-Livorno. You then need to take the exit at Albinia and follow the signs for Manciano. Simply follow the signs for Pitigliano afterward.

How to Get to Pitigliano by Bus

If you don’t feel like driving, there are daily buses that run to Pitigliano from Siena, Florence, and Grosseto.

How to Get to Pitigliano by Train

While you can’t ride a train straight to Pitigliano, you can still take it and stop at any of the following nearby railway stations:

➡️ Grosseto (80km from Pitigliano)

➡️ Albinia (50km from Pitigliano)

➡️ Orbetello (57km from Pitigliano)

➡️ Viterbo (57km from Pitigliano)

From these stations, you can catch a bus that will take you to Pitigliano.

Things to Do in Pitigliano

✔️ Explore the Jewish Quarter

The Jewish synagogue and the museum beside it are worth visiting. The museum will give you an idea of how the Jewish community has lived their daily lives. You can also see the Mikveh, which is a Jewish ritual bath where it’s believed to help people achieve purity. There’s also a butcher shop and bakery called Forno delle Azzime.

✔️ Visit Fontana Delle Sette Cannelle

If you want some nice views, I suggest visiting Fontana delle Sette Cannelle or Fountain of the Seven Spouts in English. It was built in 1545 in Piazza della Repubblica and gives you access to its surrounding magnificent views.

The fountain has seven pipes, as its name suggests, which are each decorated with a sculptured animal head. You can also see some arches that are actually an aqueduct leading to the fountain. These arches were built in the 1600s by Antonio da San Gallo il Giovane in order to supply water to the region, as instructed by the Medici family.

✔ Wander within Palazzo Orsini

If you go to Palazzo Orsini, what you’ll see is an impressive building with high crenelated walls and defensive towers. All of which are the result of several renovations starting from the Middle Ages until the 19th century.

The palace was originally used as a convent but was transformed into a fortress in the mid-13th century by the Aldobrandeschi. Around the middle of the 16th century, this fortress was significantly restructured under the dominion of the Orsini. A transformation was also done during the Lorraine period between 1777 and 1840.

Aside from its noteworthy architecture, the palace also features two museums: Museo di Palazzo Orsini and Museo Civico Archeologico di Pitigliano.

Museo di Palazzo Orsini

This gorgeous museum holds sacred art and liturgical furnishings from the Cathedral of Pitigliano and other surrounding churches.

There are 18 rooms in the entire museum, featuring some famous art pieces like the wooden statue of Madonna and Child by Jacopo della Quercia and the panel Madonna and Child with angels and saints Francesco and Pietro made by Guidoccio Cozzarelli.

Museo Civico Archeologico

This museum serves not only as a gallery but also as a restoration workshop and warehouse. It houses numerous finds from the excavations of the Poggio Buco necropolis and from the finds in Pitigliano. These pieces date back to the Etruscan era.

Where to Stay in Pitigliano

And if you’re looking for something that many other travelers confidently recommend, FicOlivo and B&B Locanda Il Tufo Rosa are two of the many accommodations with a lot of glowing reviews.

18. Monticchiello

Another hill town in Tuscany that is worth visiting is Monticchiello. It’s a small medieval village that is not often included in many traveler’s itineraries but somewhere I still recommend for you stop by. It has definitely a lot to offer not only in sights but also in culture.

Monticchiello is nearby other more famous destinations, like Siena, Pienza, and Montepulciano. It is only a small town but it boasts a stunning natural beauty and a unique theater tradition that distinguishes it from other Tuscan towns.

The town’s famous ‘poor theater’ or ‘Teatro Povero’ offers a theatrical experience that characterizes Monticchiello and its locals. It showcases the day-to-day life in the village, inspired by their local history and re-introducing the customs of rural civilization.

How to Get to Monticchiello

Despite being not as popular as some of the best towns in Tuscany, Monticchiello is easy to reach. You can drive there or opt for public transportation, which consists of a train and bus.

How to Get to Monticchiello by Car

As always, I believe driving is the easiest way to get to Monticchiello. You just have to take the A1 motorway and exit at the Chiusi-Chianciano Terme junction. About 20km ahead of it is the town of Monticchiello.

➡️ From Florence

Take north A1 then exit at Valdichiana. You then have to continue on SP327 toward Torrita di Siena, followed by SP135 and SP17 to Montepulciano. Then simply head towards Monticchiello until the SP88 turn.

How to Get to Monticchiello by Public Transportation

You can take a train and stop at the Chiusi-Chianciano Terme train station. From Chiusi-Chianciano, you can catch a bus to Monticchiello which could take about 2 hours and 10 minutes.

There are also available taxis there. Or if you want, you can drive a car from Chiusi-Chianciano to Monticchiello.

Things to Do in Monticchiello

✔ Catch one of their unique theater performances.

Every summer, there are open-air theater performances in Monticchiello. If you happen to visit during this time, I highly recommend not missing the chance to see it!

This form of theater was first introduced in Monticchiello as a community project. It was 1967 and their community was going through significant changes. The theater then became their way of expressing various thoughts and fears about the said changes.

Over the years, their ‘poor theater’ performances have broached several topics that not only concern the local community but also touch international interests.

✔ Visit the church of Saints Leonardo and Cristoforo

Pieve dei Santi Leonardo e Cristoforo was built in the second half of the 13th century with a Gothic architectural style. Its simple facade has a beautiful rose window above an ogival portal.

The interior was remodeled in the 18th century and has walls that feature many frescoes from the Sienese school. These frescoes date back to the 14th and 15th centuries.

✔ Look for the traitor’s head!

A fun challenge for anyone visiting Monticchiello is to look for the traitor’s head that was oppressed by a cannonball. Hint: It’s on the facade of one of the houses in the village streets, about 5 meters high.

This piece of art was made in the 14th century to depict the traitor who opened the city gates for the Florentine enemies in exchange for two thousand guilders.

Where to Stay in Monticchiello

These two farmhouses having glowing reviews: Agriturismo Riposati and Agriturismo Barbi.

19. Montalcino

In the province of Siena, Tuscany, you will find the interesting hill town called Montalcino. It overlooks expansive Sangiovese vineyards and offers a scenic view of Val d’Orcia. 

Montalcino gained worldwide recognition mainly for its two famous wines: Rosso di Montalcino and, of course, Brunello di Montalcino . But even if you’re not a wine enthusiast, there is still a lot in this town that can make your visit worthwhile!

The town can also interest art lovers with its museums and architectural masterpieces. Among its notable sites are the Rocca (a fortress built in 1361) and the tall clock tower. There are also several arts and crafts shops where you can stop by.

How to Get to Montalcino

There are three ways to get to Montalcino: by train, bus, and car.

How to Get to Montalcino by Car

You need to drive about 8km off the SS2 via Cassia. This road runs between Rome and Siena. 

You can easily find a rental car in Siena or Florence. And if you don’t like driving throughout your vacation, there are private drivers that you can hire as well.

How to Get to Montalcino by Public Transport (Train + Bus)

There are numerous trains that run on the Grosseto line every day. The nearest stop is at Buonconventio which is still about 14km from Montalcino. From there, you can catch a bus to Montalcino which can take about 30 minutes.

You can also ride a bus from Siena, although you have to change buses once in Buonconvento.

Things to Do in Montalcino

✔ Try Montalicino wine!

Being known for its world-class wines, especially the Brunello, it’s almost a crime not to go wine tasting in Montalcino. You simply have to taste for yourself why their wines are highly praised.

You can find a lot of ‘enotecas’ or wine repositories that offer wine tasting. And if you liked them, you can buy your favorite bottle or two. Most of the wines that they offer for wine tasting are the town’s two biggest sellers, Brunello and Rosso di Montalcino.

Brunello di Montalcino is made from 100% Sangiovese grapes and is aged for 5 years. 2 of these aging years are spent in oak barrels. Brunello can then be released for public consumption on January 1st the fifth year after harvesting.

Rosso di Montalcino is a wine made from 100% Sangiovese grapes as well. The only difference is that the aging duration is not as strict as Brunello’s. Rosso can be released to the market after only a year of aging.

✔ Explore the fortress

The Rocca or fortress in Montalcino has been dominating the town’s skyline since 1361. It was built by the Sienese to mark the passage of Montalcino under Siena’s power.

The fortress sits on the town’s highest point. And if you climb to the top of the tower, you’ll gain access to an uninterrupted view of the natural beauty of Montalcino and Val d’Orcia. You’re also allowed to walk along the walls, giving you more views of the town from different angles.

There are practically no significant changes in the fortress since the Middle Ages. Its mighty structure is now used as a venue for concerts, festivals, and other community events. And every July in the summer, the Jazz & Wine Festival makes the fortress more inviting for locals and tourists alike.

💡 NOTE:   The fortress courtyard is open to the public for free. However, there is a small fee for climbing the steps to the walls and tower.

Where to Stay in Montalcino

Check out these Montalicino accommodations that are highly rated by hundreds of people: Le Ragnaie and Drogheria e Locanda Franci .

20. San Quirico d’Orcia

San Quirico d’Orcia is one more town in Tuscany that sits prettily on top of a hill. This commune is named after Saint Quiricus and is blessed with a serene natural landscape. The magnificent views in this town include vineyards, olive groves, lovely hills, and lines of cypress trees, to name a few.

History, art, and architecture lovers will also love visiting San Quirico d’Orcia. Here you can see some medieval churches whose structure will make for memorable photographs!

During medieval times, San Quirico d’Orcia was in a strategic location where emperors, pilgrims, and merchants constantly pass through. In fact, Emperor Federico Barbarossa camped here in 1154 and met with the pope’s emissaries to talk about his coronation.

How to Get to San Quirico d’Orcia

It’s easy to get to San Quirico d’Orcia by driving. If you’re from Siena, simply take the SR2 and it will lead you straight to the heart of Val d’Orcia. 

And if you choose to try public transportation, just keep in mind that there are no train services in the actual town. The nearest station is still in Buoconvento. From there, just hop on to a TIEMME bus and you can reach San Quirico d’Orcia.

Things to Do in San Quirico d’Orcia

✔ Walk along Horti Leonini

One of the attractions you shouldn’t miss in this beautiful Tuscany town is Horti Leonini. It’s a Renaissance garden that dates back to 1581. This stunning Italian-style garden is named after Diomede Leoni to whom this land was gifted by Francesco I de’ Medici.

Horti Leonini is located in the main square of San Quirico d’Orcia. It features geometric box hedges, a crumbling stone tower, and manicured green space that makes for a relaxing strolling area.

✔ Admire the Collegiate Church of Saints Quirico and Giuditta

Collegiate Church of Saints Quirico and Giuditta is an admirable Romanesque church built with cream-colored stones. This makes the building even more attractive in daylight, beckoning tourists to look and take photos.

This church is dedicated to Quiricus, a 3rd-century child martyr. And aside from his depiction of the altar, the church design also includes the rare example of Lombard style in Tuscany.

Among the church’s three doorways, one was credited as a masterpiece of Giovanni Pisano. Other remarkable works in the church’s interior include the altarpiece by Sano di Pietro, a 15th-century painter from a Sienese school. 

✔ Celebrate Festa di Barbarossa  

As I mentioned above, Federico Barbarossa camped in San Quirico as he was on the way to his coronation. And in honor of him, the town now celebrates Festa di Barbarossa in June of every year. This fest includes people donning beautiful costumes and participating in period archery tournaments.

Where to Stay in San Quirico d’Orcia

Hotel Palazzuolo and Antica Sosta are great places to stay in San Quirico d’Orcia.

21. Anghiari

Although this is the last in my list of best towns in Tuscany, Anghiari is by no means the least of them. This hill town found in the province of Arezzo is also a charming village that still clearly depicts its medieval roots.

During the Medieval Ages, Anghiari played a vital role in war. The flat valley under it became the place where the famous Battle of Anghiari transpired in the year 1440. This is where the Florentine troops won against the Milano army.

Anghiari is enclosed in massive walls built in the 13th century. To this day, the walls still stood tall, preserving the original atmosphere in this small medieval town.

Anghiari is now considered one of the most beautiful villages in Italy and was awarded an Orange Flag distinction from the Italian Touring Club.

How to Get to Anghiari

To get to Anghiari, you can either drive a car or take public transportation.

If you’re driving from Florence, you just have to take the A1 road towards Arezzo, and then go on E78 or SP43 (Strada Provinciale della Libbia). You will then find Anghiari along E45 by the Sansepolcro exit.

For public transport, I recommend taking the train to Arezzo where you’ll then have to transfer to a bus in order to reach Anghiari.

Things to Do in Anghiari

✔ Explore the museums

The Battle of Anghiari was painted by Leonardo da Vinci to honor the victory and materialized its glory. However, the original artwork was lost. What remained is the copy made by Paul Rubens, which you can find in the Museum of the Battle and Anghiari.

There are also other museums in Anghiari, such as the State Museum and Misericordia Museum.

You can find the State Museum in Palazzo Taglieschi where it housed its prestigious art collection, including the polychrome wooden Madonna made by Jacopo della Quercia.

✔ Visit various castles and palaces.

Like the other medieval towns in Tuscany, Anghiari comes with its fair share of historical castles and palaces. Some of these are the Castle of Galbino , which was made back in the year 1000, and the Castle of Sorci , which now houses a highly acclaimed traditional restaurant.

Where to Stay in Anghiari

There are many great places to stay in Anghiari. A couple of these are Hotel La Meridiana and Locanda Del Viandante B&B .

For more options that fit your budget range and preferences in amenities, I suggest heading to Booking.com .

Bonus: Unique Day Trips from Tuscany

Just to throw in a couple of bonuses for you. Here are some great day trips in Tuscany and from Tuscany.

⭐ Florence American Cemetery

Car travel time: 40 minutes (not near a train nor town but easy access off the highway outside Florence)

For you Americans or history hounds, we chose to stop on our way back from Sienna at the Florence American Cemetery (free parking and admission). This pristine park pays tribute to the 4,402 American soldiers buried there who lost their lives during WWII, pushing up the length of the Italian countryside to clear the enemy lines. 

What a perfectly preserved place of peace. Extremely somber and mesmerizing and important and impactful. Be sure to walk to the top of the hill to read through the history of the route the battalions advanced now and forever etched into stone.

A very special place.

⭐ Asmana Wellness World Firenze

Italy is known for its wellness centers. It’s part of their culture of health.

Asmana Wellness is a wellness center and spa just outside of Florence. I’ve had multiple friends who have raved about it.  From the fresh juices to the saunas, wellness water journey, and even napping spaces, it’s the perfect place to rejuvenate your body and mind!

To get to Asmana, it’s best to have a car. However, you could take a combination of a train + bus + a little walking. 

⭐ Bagni Di San Filippo

About a 2 hour drive from Florence, Bagni Di San Filippo is an amazing giant natural mineral hot spring. It is a fabulous free way to spend a day. The white calcium waterfall seemingly frozen in time holds hot waters careening down it with cut out tubs perfect for lounging in. Named the white whale, this beast of a beauty was super relaxing and didn’t cost us a cent!

⭐ Portovenere

Located about 2.5 hours from Florence is the seaside picturesque town of Portovenere. We originally planned to take the dayboat from La Spieza to Portovenere through to Cinque Terre. However, upon arrival at the ticket booth, we discovered the seas were too strong for the ferry to turn the corner past Portovenere to Cinque Terre.

So we changed plans and chose to explore the seaside harbor town of Portovenere instead. The harbor holds multi-colored building facades and winding streets lined with shop after shop of food and flavors to fill up your day. Portovenere ended up being one of our favorite stops and less crowded than Cinque Terre!

⭐ Civita di Bagnoregio

Civita di Bagnoregio is one of the coolest towns in Italy. You can only access this quaint medieval town via the pedestrian bridge. The hill which holds Civita di Bagnergio is eroding so there aren’t many inhabitants left. Yet is still has some charming shops and restaurants and is one of my favorite day trips from Tuscany.

⭐ Lucignano

An unlucky day of the week choice for us as the museum holding the Tree of Love was closed on the Tuesday that we visited. The story of the golden gilded tree that took over a hundred years to craft led us to Lucignano but the charming concentric circling cobblestone streets on our cloudy day there brought us back in time.

We only had time for a quick stop in the quaint Collodi, but we got a glimpse of the Pinocchio crazed town including the tallest Pinocchio in the world.

How many days do you need in Tuscany, Italy?

The amount of time you need in Tuscany depends on how much you want to see. You most likely can’t see it all. I’ve spent over 4 months traveling throughout Tuscany and haven’t seen everything!

Some people come via cruise for a day and pop into Florence and maybe Lucca. Others stay for a week driving around to multiple small villages and larger towns.  And some, like myself, stay for months.

My advice is to get clear about what is important to you. When you are on your way home from your trip, what do you want to feel? What will you be glad you experienced?  If you also want to feel refreshed, remember that you don’t need to see it all. 

No matter how much time you have in Tuscany, I think Tuscany is best experienced by doing these three things:

✔️ Visiting a popular town (such as Lucca or Florence)

✔️ Visiting a smaller village

✔️ Seeing the rolling green hills (which can be done in conjunction with visiting a winery)!

What is the best time to visit Tuscany?

The best time to visit Tuscany is the Spring or Fall. The shoulder seasons essentially are when the crowds dissipate, the weather is a bit cooler and you can really enjoy the beauty in Tuscany.  Of course, truly you should visit Tuscany during the time of year that best suits your preferences. 

How to get around Tuscany?

To get around Tuscany, you can take the train, rent a car or take a bus. The other more expensive option would be to hire a driver.

If you are staying outside of the city center, I would recommend renting a car. It’s truly the best way to see the Tuscan rolling countryside and smaller villages.

FAQs about the Best Towns to Visit in Tuscany

Curious about the best towns to visit in Tuscany? Here are some of the most common questions:

Which is the prettiest part of Tuscany?

Cortona and San Gimignano are among the prettiest towns in Tuscany.

Going to Piazza Garibaldi in Cortona will give you a fantastic vantage view of its surrounding hills and valley. And if you prefer a charming cityscape, San Gimignano offers the iconic medieval towers Torre Grossa and Torre Rognosa. You can even climb inside these towers to better appreciate the panoramic view of the Tuscan countryside.

Check out some Tuscany inspiration:

Where are the best areas to stay in Tuscany?

Florence is one of the best areas to stay in Tuscany. It’s the capital city and the region’s primary tourist hotspot, which gives you a wide range of options for accommodations that fit any budget range. Also, a lot of attractions and must-try activities are conveniently nearby.

Siena is another good base in Tuscany. It’s located in the center of the region and will put you close to other must-visit places in Tuscany.

What is the safest city in Tuscany?

Florence is the safest city in Tuscany with a safety index of 70. It’s even one of the safest cities in Italy. 

You don’t have to worry about going to other places in Tuscany as well. Tuscany is considered one of the safest regions in Italy so exploring its glorious towns won’t pose too much of a risk.

However, keep in mind that safety precautions are still advisable, especially in touristy areas where pickpockets and the like may be present.

What is the most famous part of Tuscany?

The historic cities of Florence and Siena are among the most famous parts of Tuscany.

Florence is Tuscany’s main tourist hotspot and is known as the birthplace of the Renaissance. On the other hand, Siena is home to the world-renowned cathedral of Piazza del Campo, where the famous Palio horserace is held twice a year.

Pisa is also high on the popularity list. It’s mainly known for its leaning tower but also for the Square of Miracles and Arno River, to name a few.

What town is the heart of Tuscany?

Florence is mainly considered as the heart of Tuscany but others also take Pienza as the real heart of Tuscany.

Pienza is a Renaissance town that offers the most picturesque areas in Tuscany. It’s nestled on Tuscan hills where you get to see Renaissance palaces and the unobstructed view of the Val d’Orcia landscape.

If you’re going on a drive through the heart of Tuscany, your route will pass through Pienza, Montepulciano, Monticchiello, Val d’Orcia, and Bagno Vignoni.

What are some non-touristy towns in Tuscany?

Pitigliano, Barga, Suvereto, and Arezzo are some of my recommended non-touristy towns in Tuscany. You can enjoy a lot of fun activities, explore historical places, and bask in the magnificent natural view in these places without being thrust into overly crowded places.

What are the best towns near Florence, Italy?

San Gimignano, Monteriggioni, and Volterra are among the best towns near Florence, Italy. You can easily explore them by car or public transport if you choose to stay in Florence. 

Final Thoughts about the Best Towns in Tuscany

There are so many amazing towns in Tuscany. Venture out, explore the countryside, the villages, the olive farms, the wineries. Stop and enjoy the views.

My recommendation when checking out these best towns in Tuscany: Don’t try to see it all. Plan your meals around siesta so you aren’t left hungry. Go a little off the beaten path where there aren’t so many tourists. Have conversations with locals.

Enjoy all that Tuscany has to offer!

About the Author

Michelle Schomp is the co-founder and main writer of Passport Explorers.

She loves to explore new places together with her husband and three kids. And as they travel the world and gain new experiences, she loves to share everything she’s learned with all of you!

You can find more of her and her family’s adventures on YouTube .

The 5 Best Tuscany Day Trips From Florence [2024 Reviews]

If you’re already going to be in Florence, you would be missing out if you didn’t take a dedicated trip to Tuscany.

While Florence certainly has its own beauty and fascinating history, Tuscany is a great way to escape the city and into a serene realm of wine, delicious food, and rolling countryside.

There are tons of Tuscany tours out there, which can make it hard to narrow them down and choose which is best for you.

We have done the “hard” part for you, ensuring that each one of these tours are worth your time and money. Without further ado, we present to you the top day trips to Tuscany from Florence!

Be sure to see our reviews of Full Day Tuscany Day Trips, Florence Wine Tours and Cinque Terre Tours.

Best Day Trips To Tuscany From Florence

Quick answer: the 5 best tuscany day trips from florence tours.

• Best Combination Tour: Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa & Lunch at a Winery
• Best Guided Tour: Tuscany Wine & Food Tour with Guide From Florence
• Best Full Day Tour: Tuscany Wine Tasting Full-Day Trip From Florence
• Best Private Tour: Private Tuscany tour: Siena, San Gimignano and Chianti. Day Trip from Florence
• Best Budget Tour: Tuscany Day Trip with Optional Lunch and Wine From Florence

Tuscany Day Trips From Florence Reviews

1. best combination tour: tuscany day trip from florence: siena, san gimignano, pisa and lunch at a winery.

• Duration: 11-12 hours
• Departure:  Piazza della Stazione, 14/39, 50123
• Departure Time: 8:00 AM
• Includes: English-speaking driver/guide, transport by minivan, visit to Siena, San Gimignano and Pisa with lunch and wine tasting.

First up, we have an amazing full day of fun on the Tuscan countryside. The Tuscany Day Trip from Florence is a great way to see some of the most beautiful parts of Italy with a guided tour so you get to see more. Prepare for a day of knowledge, experiences, and a lot of fun as you’ll head to various cultural stops!

Start off in the morning where you will head to Siena. It feels like a part of this area never quite left the medieval ages, and is charming in its own way.

Here, we recommend you enjoy lunch in at the Pizzicheria de Miccolil. It’s half-butcher shop, half-bistro so you know your food is fresh. Did we mention it also includes a cheese and wine cellar?

Salamis and hams are abundant here, and try their delicious house-made pizza! Siena is definitely one of the most beautiful towns in Tuscany. That’s saying a lot, considering we are talking about the culture-rich Italian countryside.

Next onto the walled town of San Gimignano. One of the oldest villages in Chianti, some say it was even where Amerigo Vespucci was born. The fortified medieval hamlet is truly breathtaking with its scenery and architecture, and is known for its wine where you’ll try plenty.

Here you can go to the famous Guardastelle Vineyard where you can take a tour and taste some fine Italian wines. If your still hungry or even if your not, have some cheese and appetizers as well. Or go for a full lunch!

When you are ready for some exploring, we recommend checking out La Rocca di Montestaffoli. This 14th century fortress offers amazing views of the town.

Don’t miss the Torre Grossa. This is an ancient skyscraper, the ancients built them as well! When you climb to the top, you will be met by spectacular views of the town below.

More Information & Tour Booking

100% refund for cancellations within 24 hours of tour experience, search for other top rated florence experiences you may enjoy:, 2. best guided tour: tuscany wine & food tour with guide from florence.

• Duration: 8 hours
• Departure:  Piazzale Montelungo
• Departure Time: Morning
• Includes:  T ransportation by air-conditioned vehicle,  Wi-Fi on board,  English-speaking driver/guide, g uided visit to 3 different wineries, w ine tasting, o live oil tasting, l unch, f ree time in Greve in Chianti

If you’re a wine lover or would simply like to explore more about this world, you’re on the right track. The From Florence: Tuscany Wine & Food Tour with Guide is a bit longer, clocking in at 8 hours.

However, you’ll have time to visit 3 different wine estates and get to try all kinds of wines, olive oil, and balsamic vinegar! Another massive bonus to this tour is that they operate with very small groups, only. This means that you won’t just be lost in the crowd.

You’ll have personalized attention and can ask your guide any questions you may have. Smaller groups also allow you to simply see more!

Start off your morning by meeting at Piazzale Montelungo, where you’ll be picked up by your air-conditioned vehicle.

With wi-fi on board, you never have to worry about being out of the loop. You can go “live” on your social media platforms, send videos and photos to friends and family, post about your tour, etc. without having to wait!

However, we’re sure you’ll want to live in the moment and enjoy the beautiful scenery around you, too. As you journey around, your driver/guide will tell you and your group all about the area’s history, wine production, and other interesting facts and anecdotes.

You’ll drive south from Florence and reach your first winery where you’ll enjoy some wine and a tasty traditional Tuscan lunch.

The second winery will teach you all about the winemaking process where you’ll visit their farm and learn about where their ingredients come from. Their wine expert won’t hesitate to share interesting facts and “secrets” about their products and will give you a full tour of the space.

Make sure to try their perfectly-sweet Vin Santo dessert wine while breathing in the fresh air of the undisturbed rolling hills. Then, head to Greve in Chianti, where you’ll have some time to walk around the lovely main square which has been significant in the local community for many years.

3. Best Full Day Tour: Tuscany Wine Tasting Full-Day Trip From Florence

• Duration: 7 hours
• Departure: Piazza della Calza
• Departure Time: 9:45 am
• Includes: T our guide, t ransport for activity duration, m ap

First off, we have the From Florence: Tuscany Wine Tasting Full-Day Trip . Designed for independent travelers between the ages of 18 and 35 years old, it’s a lot of fun and relaxation with beautiful scenery to set the scene! This tour includes visits to 2 different wineries, but you’ll be able to learn about and experience much more than that!

Meet at a central pickup spot (Piazza della Calza) in Florence with the rest of your group and hop on board a luxury van! This van is climate-controlled, with a nice amount of space and comfortable seats. You’ll set off at 9:45 am, which means you still have some time to sleep in and enjoy breakfast before starting your tour.

Your first stop is San Gimignano, located in the Chiani countryside, which is what this area is renowned for. When you first arrive, you and your group will have time to stroll around at your own pace.

This really is one of the best ways to see it, as you’ll be able to see this charming town up close and be able to really appreciate the details, the friendly locals, and different shops.

After this, you’ll head to a wine tasting school (which everyone should be educated on!). Here, you’ll try 4 different wines, including the notorious Chianti Classico D.O.C.G., a Super Tuscan wine, a 30-year-old balsamic vinegar, and lush truffle extra virgin olive oil.

As you taste, a professional wine producer will teach you how to spot the different flavor profiles and help develop your skills.

Next, head to another local winery facing the gorgeous tower of San Gimignano. The winemakers really treat you like family, sharing secrets about their wine and oil, along with the best wine and oil pairings to take full advantage of these flavors.

After tastings, you’ll have the chance to purchase their wines at an affordable cost to enjoy at home or share with your friends and family.

Then, you’ll have more free time to wander around the little alleyways of San Gimignano with some of their world-famous gelato in hand!

4. Best Value Tour: Private Tuscany Tour: Siena, San Gimignano & Chianti – Day Trip from Florence

• Departure: H otel pickup and drop-off included
• Departure Time: 9:00 am
• Includes:  Driver, hotel pickup and drop-off, private tour, transport by air-conditioned minivan

If you’re looking for a comprehensive, educational tour of Tuscany but are on a tight budget, then you may be feeling like you don’t have a lot of options. However, we’re here to prove that wrong with our next tour! The Private Tuscany Tour: Siena, San Gimignano and Chianti Day Trip from Florence is just the ticket for what you’re searching for!

Clocking in at 8 hours, they really manage to pack everything in for an adventure-filled day that will never leave you with a dull moment. You’ll head out to 2 of the most charming, well-preserved Tuscan villages that will make you want to come back for more.

These villages aren’t quite as tourist-heavy as Rome or Florence, so you won’t have to worry about crowds or noisiness. Start off by being picked up at your Florence hotel and hop aboard a deluxe minivan with comfortable seats and large windows to admire the hills as you head toward your first destination.

Siena is up first, which is an UNESCO World Heritage-listed town known for its captivating cathedral and Piazza del Campo. The latter allows only pedestrians to walk around, slowing things down and allowing you to really treasure the environment and experience.

After some leisure time, you’ll head to the hilltop village of San Gimignano which is famous with its 14 towers! Located along the renowned “via Francigena” road once operated by pilgrims, it’s known for producing the white wine of Vernaccia di Sangimignano and saffron. Don’t miss its Duomo “La Collegiata” which was built in 1200 and is still surprisingly well-preserved!

5. Best Budget Tour: Tuscany Day Trip with Optional Lunch and Wine From Florence

• Duration: 12 hours
• Departure:  Santa Maria Novella train station by the taxi stand
• Includes:  Expert guide, g uided walking tour of Siena, e ntry ticket to Siena Cathedral, f armhouse lunch at a winery estate in Chianti (if lunch option selected, w ine tasting of 4 regional wines (if lunch option selected)

Lastly, we have the longest tour on the list which is perfect for those who really want the longest experience possible for a day tour.

This 12-hour tour includes skip-the-line tickets and plenty of wine tastings to make for a wonderful experience! If that sounds like fun to you, sign up for the From Florence: Tuscany Day Trip with Optional Lunch and Wine !

Your morning starts bright and early, where you’ll meet up with your guide and the rest of the group at Florence’s central train station. Your guide will greet you and sit with you, informing you of interesting stories and historical accounts of the areas you pass by.

Your first stop will be Siena, which is known as the country’s most picturesque medieval city. We can’t deny that, as even before you get to the city center you can see just how well the locals have taken care of their centuries-old city.

Admire the iconic orange terracotta roofs, contrasting the majestic gothic and Romanesque architecture of the cathedral. You’ll then head up to San Gimagnano, the UNESCO-site sitting on a hilltop.

The tower houses were constructed in the Middle Ages, and you’ll have plenty of time at your own leisure to check them and the local palaces, churches, etc. out!

You can’t miss out on a trip to Pisa and its iconic tower where you have to get some photos! Then walk around the Piazza dei Miracoli and check out other notable landmarks! Be prepared for plenty of walking but you won’t even notice it with so much going on.

What Can I See in One Day in Tuscany? (With a Sample Itinerary)

Tuscany without question is one of the most beautiful and charming regions of Italy. Even is you only have one day to spend in Tuscany, you can still see some of its best attractions.

First thing to do is head out to the countryside, where the real charm of Tuscany is. Your first stop should be the medieval town of San Gimignano. With its imposing towers, narrow alleys, and beautiful churches, its a must see! Walk around town and enjoy the views of the town and surrounding countryside.

Now its time to check out the small town of Monteriggioni. Its surrounded by 13th-century walls and towers. It’s a perfect example of medieval Tuscany and is a must visit for history enthusiasts. Walk along the town walls, explore the castle and take in the views of the Tuscan countryside.

After exploring Monteriggioni head to Siena. I think this is Tuscany’s most beautiful town. Siena is a perfect example of Italian culture and art.  It also has a beautiful medieval center that is a UNESCO World Heritage Site .

Explore the city’s narrow streets and visit the Piazza del Campo which is a Cathedral. If you have time, stop at a local trattoria and try some of the delicious Tuscan specialties, such as pici pasta or the famous bistecca alla fiorentina.

Of course one day is not enough to see everything Tuscany has to offer but this one day itinerary is a great way to hit the highlights.

What is the Best Way to do a Day Trip to Tuscany from Florence?

Getting to Tuscany from Florence is a breeze and there are several ways get there.

Guided Tours : If you’re looking for the easy button, then taking a guided tour is your best bet to see Tuscany. There are several tour operators in Florence that have day trips to Tuscany where you can sit back, relax and enjoy the beauty of the Tuscan countryside without any of the stress of planning. We have highlighted our favorite options above .

Rent a Car: If you want to explore on your own, renting a car is your best bet to explore Tuscany. Florence is well connected to Tuscany’s major cities and towns with highways, making it easy to get around. Driving through Tuscany is worth the trip with stunning views of rolling hills, vineyards and ancient towns.

Public Transportation: If you’re looking for an inexpensive option, taking a train or bus will get you to several towns and cities in Tuscany. There are several trains and buses that run between Florence and major cities like Siena, Pisa, and Lucca, allowing you to explore the region for cheap.

However you choose to get to Tuscany, the journey there is sure to be just as awesome as the destination. The beauty of Tuscany is should not be rushed so you to take in the sights of this beautiful region of Italy.

Why You Should Take a Day Trip to Tuscany

Tuscany is a region that has captured the hearts of millions of travelers for centuries and for good reason!

• The Scenery : Tuscany has some of the most stunning scenery in the world. From rolling hills covered in vineyards and olive groves to ancient towns perched on hilltops. Every corner of Tuscany is a feast for the eyes and you’ll find yourself constantly stopping to take in the views and some pictures.
• The Food : If you love Italian food then you will be in paradise in Tuscany. There are hearty soups and stews to delicious steaks and fresh pasta. You will be spoiled when it comes to dining options in Tuscany. Let’s not forget the wine! Tuscany has to some of the world’s best wineries. If you have time, taking a tour of the wineries around Tuscany is a must do!! Enjoy wines like Chianti, Brunello di Montalcino, and Vernaccia di San Gimignano. See our reviews of Tuscan cooking classes if you have the time.
• The History : With ancient towns and cities that have been standing for centuries you are surrounded by history. From the iconic Leaning Tower of Pisa to the stunning Duomo in Florence. Tuscany has some of the world’s most famous landmarks. Don’t forget the countless museums, art galleries, and churches to be explored.

Tour Guides

The City Escape Tuscany Private Day Trip is our Editors Choice for the best Tuscany day trip from Florence.

Robert Baker

Related articles, the 5 best stonehenge tours from london [2024 reviews], the 5 best florence wine tours [2024 reviews], the 7 best vatican tours ⛪ [2024 reviews], the 5 best seine river dinner cruises [2024 reviews].

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17 Best Day Tours In Tuscany You Will Love (Wine, Culture, and More!)

September 6, 2022 //  by  Follow Me Away //   Leave a Comment

Are you searching for the best Tuscany tours?

If you want to take a tour while you are in Tuscany but are afraid of paying too much or having a terrible or boring experience, rest easy!

Touring Tuscany with a professional guide is a great option if you are looking to see and experience the best without doing a ton of planning on your own.

We have been to Tuscany multiple times and have compiled this list of trustworthy tour operators in Tuscany who are worth every penny.

Whether you are taking a Tuscany road trip and want to add on some local tours, you are stopping in Italy on a cruise, or you visiting during your Italy itinerary , tours in Tuscany have the option to enrich your experience.

These best tours in Tuscany will provide you with enough options from group and private tours to half and full-day options so you can choose the tour that best suits your trip to Italy.

Whether you are looking for wine tours in Tuscany or want to see the historic sites , this region of Italy has something for everyone!

If you are looking for a trusted place to find the best Tuscany tours, get ready to find them all in one place.

Don’t forget to check out our list of the best places to stay in Tuscany !

Small Group Wine Tasting Tour to Tuscany (4.5 Hours)

Be honest, one of your main reasons for visiting Italy is to sip on some fine wine!

There are many Tuscany wine tours from Florence, and we will feature a few favorites today. Make sure to check out our list of the Best Places to Stay In Florence!

This Small Group Wine Tasting Tour to Tuscany is the perfect introduction to Tuscan wine culture.

On this wine tour in Tuscany, you will visit two wineries where you can enjoy wine paired with local produce.

The duration of the tour is just long enough for you to get a great feel for wineries in Tuscany without going overboard.

You will get to experience some historic culture and tour wineries during your time in the Chianti Classico wine region.

A wine tasting in Tuscany is a romantic thing to do during a Tuscany honeymoon !

Reserve your tour: From Florence: Small Group Wine Tasting Tour to Tuscany

You May Also Like: Siena Educational Wine Tour And Tasting (3 Hours)

Florence: Siena, San Gimignano, & Monteriggioni Day Tour (11 Hours)

Florence is a wonderful base for many of the best Tuscany tours. It is centrally located and the most popular and well-known city in Tuscany.

The Siena, San Gimignano, & Monteriggioni Day Tour will show you what the best three ancient Tuscan cities have to offer.

This tour in Tuscany is not for the faint of heart as it is a full-day tour.

That said, you will be traveling through the Tuscan hills in an air-conditioned luxury motorcoach and will have a live guide.

The best part? This tour is both historic and tasty!

If you are looking for a Tuscany wine tour and historic tour all in one, this option is the perfect choice for you as you will receive two exclusive Tuscan wine tastings.

You will love exploring these beautiful small towns in Italy on one of the best tours to Tuscany from Florence!

Reserve Your Tour Here:   Florence: Siena, San Gimignano, & Monteriggioni Day Tour

You may also love:  Montepulciano Wine Tasting and Cellar Tour (1 hour)

Pizza & Gelato Preparation Tour in Florence (3 Hours)

If you are looking for a Tuscany tour that offers something a little different and unique, then you will love this  Pizza & Gelato Preparation Class in Florence.

There is nothing better than an enjoyable day finished off with a delicious meal and the best souvenir you can bring home, the skills to recreate the dish on your own!

Not only will you learn to make classic Tuscan pizza, but you will also learn the Florentine way of preparing gelato.

This cooking tour is set in the late afternoon so while your pizza cooks you can sip a glass of included wine and enjoy an early evening meal.

Your tour guide will be a famous local chef who knows the ins and outs of Tuscan cooking. What a memorable experience!

Book Your Tour Now:  Pizza & Gelato Preparation Class in Florence (3 Hours)

You may also love: Florence: Cooking with Kids 3-Hour Experience

Pisa City Center: 2-Hour Private Tour (2 Hours)

You have heard about this famous city for years and now you will finally get to see it on this Pisa City Center: 2-Hour Private Tour .

If you prefer a personalized tour, this option is perfect for you as it is set up for 2 guests.

You will explore the Piazza dei Miracoli, admire Pisan monuments, visit the Cathedral of Pisa, and learn about Galileo’s life throughout your tour with a private guide.

You will be able to stop and ask questions, photograph, and spend time at each monument as you wish while touring in Tuscany.

All of your entrance tickets are included in the price of the tour so you will be set to go from the moment you arrive until the moment the tour concludes.

Reserve now:   Pisa City Center: 2-Hour Private Tour (2 Hours )

If you are coming from a cruise: From Livorno: Bus Transfer to the Leaning Tower of Pisa

Tuscany Truffle Hunting with Wine and Lunch (3 Hours)

If you are looking for a really unique Tuscan experience, then you need to book this Tuscany Truffle Hunting with Wine and Lunch tour!

On this tour, you will head into the forest with a knowledgeable guide and truffle hunting dogs.

If you are looking for some fun, cottagecore vibes, you cannot miss out on this opportunity!

After searching for truffles, you will enjoy a delicious 4-course lunch with a wine tasting.

This is will be the highlight of your time in Tuscany! Who doesn’t like running around a forest with dogs?

Book Here: San Gimignano: Tuscany Truffle Hunting with Wine and Lunch

Guided Walking Tour Of Florence (2.5 Hours)

Florence is the birthplace of the Renaissance and a Guided Walking Tour is the perfect introduction.

The best way to explore any city is to walk through it and the experience is even better when you are accompanied by a knowledgeable local guide.

On this 2.5 hour Florentine Tour , you will be able to see fantastic monuments such as the Ponte Vecchio bridge and the Basilica di Santa Croce all while learning about Florence’s journey through the Renaissance.

This easy Tuscany tour is a great morning or afternoon excursion before lunch or dinner and the cost won’t break the bank either so you have some extra cash for another class of wine!

After the walking tour, go take a tour of the Duomo ! It is a can’t-miss site in Florence.

Reserve now: Guided Walking Tour Of Florence (2.5 Hours)

You may also like: Private Tour Of Florence (4 hours)

Chianti Afternoon Tuscany Wine Tour (5 Hours)

This focused Tuscany wine tour will take you through the beautiful Chianti wine region where you will see vineyards unfold before your very eyes.

During the  Chianti Afternoon Tuscany Wine Tour , you will enjoy delicious Chianti wines, Tuscan products, and rolling hills and vineyards.

You will stop at two wineries and will visit two historic wine cellars to learn about how Chianti wine is made.

You will also have the chance to try cured meats and cheeses along with your wines.

The best part of this tour is that you will be able to see one of the oldest medieval walled cities in Italy.

As far as wine tours in Tuscany go, this one ticks all the boxes for food, flavor, and fun for anyone who loves wine!

Book your wine tour now:   Chianti Afternoon Tuscany Wine Tour (3 Hours)

Florence Hop-on Hop-off Bus Tour (24 Hours)

Florence is one of those cities you want to learn everything about!

What better way to do that than on this  Florence Hop-on Hop-off Bus Tour ?

This is one of the only Tuscany tours of this kind, so if you love bus tours, this will be the one to book.

Of course, walking through the city is great, but we particularly love hop-on-hop-off bus tours because they allow you to see the major sites of the city without having to worry about transportation or directions.

While you are riding on this bus tour in Tuscany, you will also have an expert local guide who will point out sites along the way and in-between destinations!

You can purchase tickets good for 24, 48, or 72 hours depending on the length of time you want to allow for this Tuscany tour.

This tour will help you see all the amazing things to do in Florence !

Reserve here:   Florence Hop-on Hop-off Bus Tour

Carrara Marble Quarries Tour by Jeep (2.5 Hours)

Looking to break up the wine and cheese with one of the more adventurous Tuscany tours?

The  Carrara Marble Quarries Tour by Jeep is a whirlwind 2.5-hour adventure that you will most certainly be writing home about.

We bet that you have probably never even heard of the Tuscan Carrara Marble Quarries before this post, and you are going to love this hidden gem in Italy .

These mines have provided marble to Italy for centuries and many cities utilized the marble including Rome.

Your 4WD adventure will take you into two quarries, including an underground one.

You will also have the chance to taste some Lardo di Colonnata IGP during one of the more unique Tuscany tours.

Book now:   Colonnata: Carrara Marble Quarries Tour by Jeep

Pisa, Siena & San Gimignano Day Trip with Lunch & Siena Tour with Cathedral (12 Hours)

Short on time or just don’t want to beat around the bush?

This  Pisa, Siena & San Gimignano Day Trip with Lunch & Siena Tour with Cathedral will show you the best of what Tuscany has to offer all on one tour.

One of the most comprehensive day tours in Tuscany, this tour will show you Pisa, San Gimignano, and Siena which are some of the most beautiful cities in the region.

If you don’t have time for one of the many Tuscany wine tours, don’t worry, there is a wine tasting on this tour as well.

Your admission fees are included and you will eat a Tuscan lunch at a winery on this full-day tour in Tuscany.

One of the things that set this tour apart from other Tuscany tours is that you have the option to book pick-up on demand which means the tour company will pick you up from your hotel.

Overall, this is one of the Florence to Pisa tours if you want to check out the famous city.

Reserve Here:   From Florence: Pisa, Siena & San Gimignano Day Trip with Lunch & Siena Tour with Cathedral

You May Also Love: Brunello di Montalcino Full-Day Wine Tour with Tastings

Medici Family History Tour (2 Hours)

If you are looking for something fun and informative to do, the Medici Family History Tour may be perfect for you!

While visiting the Palazzo Medici, a famous architectural work of the fifteenth century, you get to also visit a secret place where Michelangelo learned to sculpt during this adventure.

This symbolic tour lets history buffs relive the betrayal and victories of the famous Medici family while exploring some of the most famous architectural buildings and also visiting where many scenes of the TV series “The Medici” took place!

If you’re a fan of the show, we highly recommend checking this out!

Book Here: Florence: Medici Family History Tour

Florence: Evening Food Tour (3.5 Hours)

There is no denying the fact that one of the best things about visiting Italy is the food, so is there a better way to enjoy Tuscany tours other than by booking a food tour?!

The Florence Evening Food Tour is unique, as you and your small group can explore the other side of Florence, which is called the Oltrarno, to experience a less-than-touristy night of mouthwatering food.

While you will be walking a bit during this tour, you also get to explore the ancient and medieval neighborhoods around the Oltrarno area in addition to getting to know genuine Italian food traditions and local, craft beer.

Of all the best tours in Tuscany, this one lets you eat your heart out: from cured meat and cheese, to beer samples, to family-owned bakeries and more, you will leave feeling stuffed!

This is one of the most delicious and best tours in Florence, Italy!

Book Here: Florence: Food Evening Tour

Museo Galileo Small Group Tour (1.5 Hours)

If you are looking for a fun and unique Tuscany tour, you might want to consider checking out the Museo Galileo Small Group Tour .

The Museo Galileo is one of the most famous international institutions dedicated to the history of science.

On this 90-minute small-group tour, an official guide will reveal all of this museum’s secrets to you.

From getting to know some of the scientific tools made by Galileo himself, this Tuscany tour lets you set back in time to admire science and history and is perfect for a short tour/adventure to squeeze in between your sightseeing adventures!

This is one of the best Tuscany small group tours!

Book Here: Florence: Museo Galileo Small Group Tour

Inferno Florence Private 3-Hour Tour (3 Hours)

There’s no denying the fact that Florence is a city full of mysteries and secrets, and Tuscany tours like the Inferno Florence Private 3-Hour Tour allow you to explore the city’s secrets in a unique and unusual way.

During this tour, you can follow the “main character” of Dante Alighieri’s Inferno on his adventures, exploring the nine circles, seven sins, and one terrifying secret.

This private tour is fun and mixes history, literature, science, and art together while immersing yourself in Florence.

From learning about the Middle Ages to exploring the Palazzo Vecchio and Baptistry, this is a guided tour in Tuscany you may not want to miss!

Book Here: Inferno Florence Private 3-Hour Tour 

Chianti and Castles Tour with Wine Tastings (5 Hours)

The sounds, scents, and flavors of Chianti will capture your senses, and this is a must-do Tuscany tour, as it is one of the best Tuscany wine tours around.

Expert tour guides will lead you around the uncontaminated landscapes of the Chianti area and you’ll get to visit these vineyards that are well known for their color– so make sure to bring your camera!

But better yet, this Chianti and Castles Tour with Wine Tastings also lets you explore ancient churches, medieval Tuscan castles , and small villages throughout your five-hour adventure.

From trying bruschetta to wine tasting to visiting historical buildings and breathtaking landscapes, this is one of the best Siena tours to choose from!

Book Here: From Siena: Chianti and Castles Tour with Wine Tastings

Discover Cinque Terre From Florence (13 Hours)

If you don’t mind long Tuscany tours and are looking for a slice of paradise during your trip, you might want to check out the Cinque Terre Full-Day Trip !

This tour lets you discover the hidden gems of the Cinque Terre regions, allowing you to explore the ancient fishing villages of Manarola, Riomaggiore, Monterosso, and Vernazza.

Spend time marveling at the rocky coast of the Ligurian Sea.

It is breathtaking and offers fantastic seaside views that you may want to check out.

The seaside is wonderful, and be careful, because once you visit, you may not want to leave!

There are so many fun things to do in Cinque Terre ! Plus, there are a bunch of beautiful places to stay in Cinque Terre on your next visit!

Book Here: From Florence: Cinque Terre Full-Day Trip

Visit the Accademia Gallery with Reserved Entrance (1 Hour)

If you are visiting Tuscany and Florence, stopping by the Accademia Gallery is a must! It is one of the best things to do in Italy !

This Tuscany tour will only take about an hour of your day, as the Accademia Gallery: Tour is the perfect one-stop-see-all moment!

This tour lets you discover and understand the creation of Michelangelo’s famous masterpieces and lets you explore the halls of the Accademia gallery, which are filled with Florentine paintings from the 15th century.

With this relaxed yet informative atmosphere, this is the perfect tour for art lovers and helps you cross off some of the most iconic sights to see in a short period of time!

Seeing David in person is one of the top things to do in Tuscany , so you cannot miss out on this tour!

Book Here: Accademia Gallery: Tour

Whether you are looking for wine, adventure, or culture, these best Tuscany tours offer something for everyone.

All of these guided tours in Tuscany are worth every penny and you will not be disappointed.

They are also quite affordable for what they offer so you can’t go wrong no matter which tour in Tuscany you choose.

Which one of these Tuscany tours are you most excited about? Let us know in the comments below!

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Tuscan Escapes

A truly tuscan experience.

Daily departures from Siena, travel in a small group of maximum 8 participants to ensure a personal experience.

Visits at a leisurely pace throughout the day, wine regions and main hill towns of central Tuscany, tour wineries and enjoy lunches on farms.

Experiences

Coming to Siena? Get an understanding for the city and its surroundings on city tours, hikes and activities. Admire the natural and artistic beauty and savor the delicious wine and food in classes.

Tour Schedule

Prefer to go Private?

Need a more exclusive or custom experience? we have made it easy for you to find what you need.

Hire a city guide for museums and city center tours  

Request a guide in your language  

Privately led by expert official guides

Book a Hiking or Biking Guide   

Customize your outing to the preferred level of physical activity

p rivate transportation and expert local driver-guide  

Tour wineries and farms  

Visit historical centers and hill towns

Transport between destinations    

Stop for lunch and visit towns and sights en-route

When staying in a Private Villa or apartment in Tuscany and you would like an activity or special meal provided for you, make your specific request. We love challenges and catering to different requests.

We are based out of Siena, so we only cater to villas situated in the vicinity of Siena (50km Radius)

Some of the activities we provide, include. Chef hire for meal preparation, wine and food guided tastings, arts and crafts workshop, live music and entertainment. 

Book Private Service

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Where Every Day is a Masterpiece

The BEST Tuscany Tours & Day Trips

Book wine tours, vespa experiences, cooking classes, and more.

Tuscany is a large region and home to many cities, including Florence, Sienna, Lucca, San Gimignano, and more, but where do you start? When most people think of Tuscany they are not thinking of a city like Florence, they're dreaming of rolling hills and curated rows of olive trees and grape vines! Below you'll find tour options to choose from, including day trips to Pisa, Sienna, wine country, Chianti, and even Vespa rides outside Florence!

17 Tours Found

Price - Lowest First

Price - Highest First

Most reviewed

Most Popular

Tuscany Wine Tour by Vespa from Florence

Taste the food and wine of Chianti as you ride through the Tuscan countryside on a vintage scooter

Pisa and Lucca Day Trip from Florence

Book a stress-free trip to see the Leaning Tower of Pisa and Lucca's medieval walls in a day

Tuscany Wineland Safari from Florence

Get off the beaten track to explore vineyards, castles, food, and Chianti wine on this 4x4 day tour

Tuscany Wine Making Experience and Gourmet Dinner from Florence

Dine like Tuscan royalty and create your own Chianti wine blend on this small group VIP evening tour

Tuscany Day Trip from Rome with Vineyard Lunch and Wine Tasting

Wander through the medieval towns of Montepulciano and Pienza and enjoy a 3-course meal!

Brunello di Montalcino Helicopter Tour from Rome or Florence

Soar above Tuscany on an exclusive VIP tour, complete with private wine tastings and a gourmet lunch

Orvieto, Civita di Bagnoregio & Winery Private Day Trip from Rome

Escape the city on a memorable journey through Umbria’s historic towns to taste fine local wines

Private Wine Day in the Chianti Hills from Florence

Enjoy an intimate day trip tasting wine and organic food from local farms and vineyards in Tuscany

Authentic Tuscan Cooking Class in Florence with San Lorenzo Market

Create delicious pasta, tiramisu, and more with market-fresh ingredients and an expert local chef

Chianti Vineyards Tour and Wine Tastings from Florence

See two luxurious wine estates, taste local wine, and sample delicious produce on this half day tour

Vintage FIAT 500 Self-Drive Tuscany Tour from Florence

Get behind the wheel of an iconic Italian car, cruising to the Tuscan countryside

Tuscany Winery Tour and Gourmet Bites in Montalcino

Pair irresistible wine with delicious gourmet bites after strolling through picturesque vineyards

Brunello di Montalcino Winery Tour & Tasting

Sip wine and stroll through vineyards alongside an expert guide in the hills of Montalcino

Private Vintage FIAT 500 Chianti Tour with Driver from Florence

Cruise through the hills of Tuscany in style and dine at a Tuscan villa on this exclusive experience

Pizza and Gelato Cooking Class in a Tuscany Farmhouse in Florence

Pick fresh ingredients and learn to make authentic, Italian cuisine on an unforgettable day trip!

Things to do in Florence

Florence Tours | Accademia Tours | Tuscany Tours | Florence Food Tours | Florence Wine Tours | Florence Full Day Tours | Florence Half Day Tours | Day Trips from Florence | Florence Duomo Tours (Santa Maria Del Fiore) | Florence Cooking Classes | Florence Food Tours | Ponte Vecchio | Private Accademia Tours | Private Uffizi | Statue of David Tours | Pisa Tours from Florence | Florence Dome Climb Tours | Florence Tours with Transportation | Florence Museum Tours | Florence Tours Likely to Sell Out | Florence Shore Excursions | Florence Attractions

OUR BEST SELLING TOURS AT A GLANCE

Most Popular Tours

Privileged entrance vatican tour with sistine chapel.

Skip the line and gain direct access to the Raphael Rooms, Creation of Man, and St. Peter's Basilica

Rome in a Day Tour with Colosseum and Vatican Museums

Explore the Sistine Chapel, St. Peter's Basilica, Roman Forum, Pantheon, Trevi Fountain, and more!

Ultimate Palace of Versailles Tour from Paris

Breeze past the lines for the palace and gardens with a friendly English speaking guide

St. Mark’s Basilica & Doge’s Palace Half-Day Tour with Gondola Ride

Explore St. Mark's Square's most iconic attractions with skip-the-line tickets and an expert guide

St. Peter's Dome Climb and Sistine Chapel Combo Tour

Begin your day early and see Rome from above, the Papal Crypts below, and the Vatican museums nearby

Ultimate Venice in a Day with Murano and Burano

Do more in a day: St. Mark's, Doge's Palace, glassblowing and lacemaking demos, and a gondola ride

Venice in a Day Tour with Gondola Ride

Visit St. Mark's Basilica, Doge's Palace, Rialto Bridge, and the hidden areas of Venice

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15 Best Tuscany Wine Tours & Wine Tastings for 2024

Thinking About Visiting Tuscany in 2024? Book Some of the Best Tuscany Wine Tours to Experience the Region Like a Local

Italy has been a popular destination for #Winetravelers this year. We’re frequently asked how to best navigate popular regions such as Tuscany , and there really is no better way to fully immerse yourself in the region than by using a guided wine tour or tasting experience that’s operated by a local. With insider knowledge, not worrying about planning, logistics or driving, you can have a much more fulfilling time exploring the region, and usually save yourself a lot of stress and time.

RELATED: Table for Two in Tuscany: Romantic Itinerary for Places to Eat, Stay, Drink & Explore

All of that being said, we’ve compiled a list of the top wine tours in Tuscany based on reader feedback and ratings. These tours include both group experiences, as well as options for private wine tastings and excursions throughout Tuscany. Whether you’re staying within the Tuscan countryside or you’re looking for a day trip from Florence , Rome or Siena , we have you covered below.

Note that for a limited time, we’ve partnered with Viator to provide our readers with secure advanced booking, free cancellation as well as an exclusive 15% discount on any wine tours that are booked via Winetraveler.com . Simply use code WINETRAVELER15 at check out.

RECOMMENDED: Stay at These Luxury Tuscan Vineyard Resorts While You Visit Tuscany

Horseback Ride and Poolside Day Chillout with Tuscan Lunch

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Florence serves as an ideal base for Tuscany wine tours due to its central location within the region, providing easy access to renowned wine areas such as Chianti, Montepulciano, and Montalcino. Its well-connected transportation system, including train routes and bus lines, ensures hassle-free travel to various vineyards and wineries.

RELATED: The Best Tuscany Wineries, Hotels & Vineyard Resorts to Experience

Additionally, numerous tour operators within Florence offer curated wine experiences that cater to a range of preferences, from small boutique wineries to larger renowned estates. This, combined with the city’s own rich cultural and culinary scenes, makes Florence the perfect starting point for exploring Tuscany’s wine country.

Tuscan Safari: Tuscan Villas with Vineyards, Cheese, Wine & Lunch from Florence

Winetraveler Rating (over 3,165 reviews):

Italy’s iconic Tuscany region is more than just a destination – it’s a feast for all your senses. This full-day Tuscany wine and food tour, departing from Florence, offers you the chance to taste the region’s finest offerings, guided by experts with in-depth local knowledge.

Navigate the enchanting Tuscan countryside in a comfortable 4×4 minibus, stopping to explore a historic wine estate and villa, and a cellar filled with delectable Chianti Classico. Each stop on your journey is an opportunity to learn more about wine and olive oil production, and to indulge in locally-sourced cheese and other Tuscan delicacies.

This unique journey culminates in a traditional 3-course Tuscan lunch at a winery restaurant with breathtaking views. Experience the magic of the Chianti region as you dine amidst vineyards under the Tuscan sun.

This particular tour, operated by Walkabout Tours, has been designed to ensure a seamless and enriching experience for our #Winetravelers.

Highlights:

• Full-day wine and food tour from Florence, with 4×4 off-road minibus transportation.
• Traverse the scenic Tuscan countryside on an off-road adventure.
• Delight in a traditional Tuscan lunch at a picturesque winery restaurant.
• Explore a historic wine estate, with a guided tour of wine, extra-virgin olive oil, and cheese tastings.
• Visit a second winery for a deeper dive into the renowned Chianti Classico wine.

15% Off With Code WINETRAVELER15

Florence Vespa Tour: Tuscan Hills and Italian Cuisine

Winetraveler Rating (over 2,896 reviews):

Venture off the beaten path and explore the heart of Tuscany on a classic Vespa scooter. This unique tour, offered by Walkabout Tours, takes you on a scenic ride through the Tuscan hills, starting from the Renaissance city of Florence. With a knowledgeable local guide leading the way, you’ll discover hidden gems such as the Piazzale Michelangelo and the Church of San Miniato al Monte.

RELATED: 25 Best Things To Do in Florence Italy: Visitor’s City Guide

The adventure doesn’t end there. After exploring the picturesque countryside, head back to a welcoming country estate to indulge in a delicious traditional Italian meal. Feast on a menu of mouth-watering bruschetta, perfectly cooked pasta, and a flavorful cheese and salami board. Experience the authenticity of Tuscany as you dine surrounded by its natural beauty.

To ensure a truly personalized and intimate experience, this tour is limited to 15 travelers.

• Explore the Tuscan hills on your own Vespa scooter, led by a local guide.
• Discover lesser-known sights such as the Piazzale Michelangelo and the Church of San Miniato al Monte.
• Delight in a traditional Tuscan meal at our country estate, featuring local favorites like bruschetta, pasta, and a cheese and salami board.
• Enjoy the personalized attention offered by small-group tours with a maximum of 15 participants.

This Vespa tour in Tuscany, presented by Walkabout Tours, gives you a unique opportunity to experience Tuscany’s charming countryside in an authentic and memorable way. Don’t just visit Tuscany, live it like a local!

Grab this opportunity to explore Tuscany in the most Italian way possible. Reserve your spot now as this is one of the best selling Tuscany wine tours currently.

Tuscany Bike Tours: One Day Bike Tour through the Hills of Tuscany

Winetraveler Rating (over 1,158 reviews):

Escape the bustling city of Florence and immerse yourself in the natural splendor of the renowned Tuscan countryside. Offered by Tuscany Bike Tours, this top-rated bike tour combines the awe-inspiring scenery of Tuscany, a rich history that spans centuries, and an authentic taste of the region’s flavors in an exciting and active way.

Pedal across fertile valleys and hilly landscapes adorned with olive trees and vineyards, stopping to explore a 12th-century villa and indulge in a traditional Italian restaurant for a mid-day meal. Recharge and enhance your journey with tastings of Chianti wine and local olive oil – the signature flavors of Tuscany.

• Cycle through the beautiful Tuscan countryside, leaving the city behind.
• Enjoy a wine tasting at a medieval castle and savor a delectable lunch at a local restaurant.
• Engage in an active and refreshing journey, a welcome alternative to being confined on a bus.
• Join the ranks of satisfied travelers who’ve showered this bike tour with hundreds of 5-star reviews.

Experience the Tuscan region in a refreshing and dynamic way. The inviting landscape, the ancient history, the flavors of the region – all come together on this journey to provide an unforgettable Tuscan experience.

Ready for the ride of a lifetime? Secure your spot on this Tuscany Bike Tour today.

Pizza and Gelato Cooking Class at a Tuscan Farmhouse from Florence (with wine, of course)

Winetraveler Rating (over 3,633 reviews):

Embark on a delightful culinary adventure near Florence, nestled within a picturesque Tuscan estate. Ideal for culinary enthusiasts and culture lovers, this unique experience allows you to learn the art of crafting two of Italy’s culinary treasures – pizza and gelato, guided by a professional Italian chef.

This interactive, hands-on cooking lesson culminates in a delicious 3-course feast of appetizers, freshly made pizza, and delectable gelato, all paired with a selection of fine wine and beer. To keep the magic of this culinary adventure alive, you’ll also receive a recipe booklet to take home and hone your new skills.

• Participate in a pizza and gelato cooking lesson, right in the heart of Tuscany.
• Learn the art of crafting two iconic Italian delights under the guidance of a professional chef.
• Relish a 3-course meal accompanied by wine or beer, all set within a charming Tuscan estate.
• Enjoy round-trip transportation from central Florence for a hassle-free experience.

Why Choose this Tour? This gourmet cooking class pairs two beloved Italian classics with the unbeatable scenery of Tuscany, creating an immersive experience that surpasses any restaurant setting.

Ready to create some delicious memories? Book this culinary adventure now and add a slice of Tuscan flavor to your journey. Unleash your inner chef and bring a piece of Italy back home with you.

Tuscan Wine Tour with Lunch, Visit to San Gimignano & Organic Wineries

Winetraveler Rating (over 547 reviews):

Take a break from the energetic pace of Florence and set off on a journey into the heart of the Tuscany wine region. This day trip includes round-trip transport from a central Florence location, making your adventure as comfortable as possible.

In the company of your knowledgeable guide, you’ll gain valuable insights into the intricate winemaking process at local vineyards, typically overlooked by many visitors to Tuscany. The day’s schedule is thoughtfully designed to include wine tastings, an authentic Tuscan lunch, and ample opportunities for capturing beautiful photographs against the backdrop of Tuscany’s scenic landscapes.

• Savor tastings of Chianti wines and relish a traditional Tuscan lunch.
• Benefit from the expertise of a guide, ensuring a stress-free exploration without the need for navigation.
• Gain insights into the winemaking process unique to the Chianti region.
• Enjoy hassle-free, round-trip transportation from a central Florence location.

Discover the serenity and charm of Tuscany’s renowned wine region with this insightful Chianti day trip. Immerse yourself in the winemaking heritage, savor authentic Tuscan cuisine, and capture memories set against Tuscany’s breathtaking vistas.

Ready to uncork the magic of Tuscany & Chianti? Book this day trip now and delve into a world where the essence of Tuscany comes alive in every vineyard, every glass of wine, and every plate of food.

Self-Drive Vintage Fiat 500 Tour from Florence: Tuscan Wine Experience

Winetraveler Rating (over 415 reviews):

Embark on an Italian adventure like no other as you couple a wine tasting experience with a classic Fiat 500 tour. Departing from Florence, step into the driver’s seat of a beautiful 1960s Fiat 500 model, and journey through the Tuscan hills as part of a scenic convoy. The tour reaches its crescendo as you park your vintage ride at a stunning 15th-century wine estate and villa.

• Enjoy a self-driven Fiat 500 tour from Florence, highlighting the esteemed wines of Tuscany.
• Visit a captivating 15th-century Renaissance villa and wine estate nestled in the Tuscan countryside.
• Immerse yourself in the estate’s vineyards and cellars, indulging in tastings of several locally produced wines.
• Travel through the scenic Tuscan hills with confidence, guided every step of the way.

Explore the splendors of Tuscany in an unforgettable way. From the thrill of driving a classic Fiat 500 through the picturesque hills, to the rich taste of Tuscan wines in a historic setting – this tour promises a feast for the senses.

Ready to drive into a day of Tuscan delights? Reserve your spot now and create memories that will last a lifetime.

Private Tuscany Wine Tour Experience from Florence

Winetraveler Rating (over 54 reviews):

Delve into the heart of Tuscany’s world-renowned flavors and stunning landscapes on a private wine tour from Florence. Journey through the picturesque hills and vineyards in the company of a knowledgeable sommelier guide, visiting three distinctive estates to sample top-notch regional wines and olive oil.

The journey includes a visit to a family-owned winery, where a traditional Tuscan lunch, paired with an array of fresh local products and wine, awaits you. Gain insights into traditional winemaking processes through a cellar tour and engaging conversations with winemakers.

• Full-day private wine tour from Florence, removing any uncertainty about selecting wineries, thanks to your expert sommelier guide.
• Explore three diverse wineries, including quaint family-run and organic estates.
• Discover the winemaking process through an immersive cellar tour.
• Savor a range of the region’s best varietals.
• Enjoy an authentic Tuscan lunch crafted from locally produced ingredients.
• Benefit from the flexibility to tailor your itinerary to your preferences.

Embark on a journey of flavor and beauty in the Tuscan region. From the quaint charm of family-run vineyards to the vibrant taste of Tuscan wines and the warm hospitality of the locals, this tour promises a truly enriching experience.

Winetraveler Rating (over 15 reviews):

Trade the bustling streets of Florence for a day of tranquility immersed in nature. Experience a horseback riding adventure through the picturesque Tuscan countryside, capped off with downtime at an elegant country resort nestled within the verdant Florentine hills. Indulge in a delightful Tuscan lunch served poolside and complemented by local Chianti wine.

• Escape the crowds of Florence and embrace the tranquility of the Tuscan countryside.
• Absorb the lush landscapes from the unique perspective of horseback riding, suitable for all levels.
• Enjoy a private experience tailored exclusively for your party.
• Benefit from round-trip transfers from Florence for a hassle-free day.

Immerse yourself in the calming serenity of Tuscany’s nature. From the thrill of horseback riding through picturesque landscapes to relaxing at an elegant resort with a refreshing poolside lunch, this day promises a rejuvenating escape from the hustle and bustle.

Tuscany Wine Tours from Rome

While Rome is not located in Tuscany, its position and connectivity make it a viable alternative base for Tuscany wine tours. Rome’s strategic location allows for comfortable day trips to southern Tuscan areas like Montepulciano and Montalcino, both renowned for their exceptional wines. The Italian capital boasts excellent high-speed rail links and highway networks that can transport you to the heart of Tuscany in just a couple of hours. This flexibility allows you to explore Tuscany’s world-class vineyards and return to Rome’s vibrant nightlife and historical attractions all in one day, offering a rich, balanced travel experience.

Tuscany Wine Tour from Rome with Private Driver

Winetraveler Rating (over 6 reviews):

Make the most of your time with this private tour that covers three enchanting hill towns in Tuscany and Umbria in just one day. With the convenience of hotel pickup in Rome and a full day’s transport, you can indulge in wine tasting in Montepulciano, savor the renowned pecorino cheese in Pienza, and admire the breathtaking views from the cliffside town of Orvieto.

• Benefit from round-trip private transportation from your hotel or chosen location in Rome.
• Enjoy ample free time to explore and shop in the beautiful towns of Montepulciano, Pienza, and Orvieto.
• Experience the unique flavors of Tuscan wines, cheeses, and other gourmet delights.
• Take advantage of a private day trip for greater flexibility and personalized attention.

Embark on a journey through the scenic landscapes of Tuscany and Umbria. Savor the exquisite flavors of the region, marvel at the panoramic views, and soak up the unique charm of these picturesque hill towns.

Winetraveler Rating (over 5 reviews):

Trace the footsteps of the Etruscans as you visit the picturesque medieval settlements of Montepulciano and UNESCO–listed Pienza, two of Tuscany’s most charming hilltop towns. Starting from Rome, this tour offers a comfortable journey in an air-conditioned minivan, giving you ample time to explore the historical streets at your own pace. Revel in the magnificent panoramas over the Val d’Orcia, with round-trip transport from your Rome hotel included.

• Explore the enchanting towns of Montepulciano and UNESCO–listed Pienza in a single day.
• Enjoy ample free time to discover the rich history and culture of these sites at your own pace.
• Be captivated by the panoramic views of the Val d’Orcia from the vantage point of Pienza.
• Benefit from round-trip transportation in an air-conditioned minivan from your Rome hotel.

Step back in time and explore the medieval charm of Tuscany. From the Etruscan roots of Montepulciano to the UNESCO-listed beauty of Pienza, this tour offers a captivating look into Tuscany’s past.

Tuscany Wine Tours from Siena

Tuscany hiking tour from siena including wine tasting.

Winetraveler Rating (over 47 reviews):

Join us as we step back in time, tracing the footsteps of ancient pilgrims along the Via Francigena, a historic route that connected Canterbury, England, to Rome. This rural path winds through charming villages, vineyards, and some of Tuscany’s most picturesque landscapes. The journey concludes in the enchanting medieval village of Monteriggioni, where you’ll be rewarded with a curated wine tasting. To wrap up your adventure, we’ll provide a train ticket for a comfortable return to Siena.

RELATED: Here’s Why You Should Include Siena on Your Next Trip to Italy

• Enjoy a half-day hiking tour from Siena coupled with a delightful wine tasting.
• Follow sections of the historic Via Francigena, a key pilgrimage route leading to Rome.
• Absorb the history of the route from our expert guide.
• Traverse between Siena and the medieval walled village of Monteriggioni.
• Bask in the captivating Tuscan vistas of rolling hills blanketed in vineyards and olive groves.
• Immerse yourself in local flavors during an educational wine tasting session in Monteriggioni.
• Take advantage of the included train ticket for a convenient return to Siena.

This is more than just a hike; it’s an invigorating journey through history and a celebration of Tuscany’s beautiful landscapes and rich flavors. Ready to walk the ancient paths and savor the local wines? Book your spot today!

Winetraveler Rating (over 122 reviews):

Tuscany is famed worldwide for its exceptional wines. Get an insider’s view into this illustrious industry with a tasting tour in the vineyards close to Siena. This intimate tour, limited to just 12 participants, takes you to a historic cellar where you’ll refine your palate and learn to distinguish delicate flavors under the guidance of a sommelier. With a choice of morning or afternoon departure, you can conveniently fit this experience into even the most packed sightseeing agenda.

• Break away from the city and effortlessly explore the vineyards surrounding Siena.
• Sharpen your palate to discern subtle flavors under the guidance of a trained sommelier.
• Choose from two departure times throughout the day for your convenience.
• Benefit from personalized attention in a small group limited to 12 participants.

Unleash your inner wine connoisseur on this exclusive tasting tour. From exploring historic cellars to learning from a knowledgeable sommelier, this experience brings you closer to Tuscany’s rich wine culture.

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Experience the unique thrill of hunting for Italy’s coveted tubers in the Tuscany countryside during an authentic truffle hunt near San Miniato. Join Francesca, a seasoned forager, and her truffle-hunting dog for a leisurely stroll through the woods in search of fresh truffles. After the hunt, unwind at her family farmhouse, where a mouth-watering lunch featuring the day’s truffle harvest awaits.

• Engage in the age-old tradition of truffle hunting with an experienced local “tartufaio” in Tuscany.
• Enjoy a walk through the woodlands near San Miniato with a specially trained truffle dog.
• Relish a satisfying lunch featuring bruschetta and pasta adorned with freshly found truffles, followed by dessert.
• Enjoy the warmth of local hospitality during this immersive experience at a family-run farm.

Embark on a truly unique Tuscan journey. From the exciting pursuit of truffles to the exquisite flavors of a truffle-infused lunch, this experience offers a deep dive into the tradition and culinary richness of Tuscany.

Tuscany Travel Logistics

Getting to tuscany.

Florence Airport, Peretola (FLR): Known as Amerigo Vespucci Airport, it’s the closest airport to the heart of Florence and Tuscany. It’s relatively small and offers fewer international connections, but it’s a popular choice due to its proximity to Tuscany’s major cities. Browse current flight deals and book as the best rates arise using Kayak.

Pisa International Airport (PSA): Also known as Galileo Galilei Airport, this is the largest airport in Tuscany with more international flight connections. Pisa airport is well-connected to Florence and other Tuscan cities by both train and bus services.

Bologna Guglielmo Marconi Airport (BLQ): Although not located within Tuscany, it’s another good option to consider as it has strong flight connections, both domestic and international. It’s roughly an hour and a half’s train ride to Florence.

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Arriving from Other Parts of Italy

Tuscany is well-served by Italy’s extensive train network. The high-speed trains from cities like Rome, Milan , and Venice make getting to Tuscany both quick and convenient. Florence’s main station, Firenze Santa Maria Novella, is a major hub connecting Tuscany to the rest of Italy.

Getting Around Tuscany

Public transportation.

Trains: The train network in Tuscany is quite extensive, connecting not only the major cities but also smaller towns. They are generally punctual, affordable, and efficient.

Buses: For some of the smaller towns and villages, bus is the only public transport available. Although they can be less predictable than trains, buses can get you to places trains can’t reach.

Renting a car can be an excellent option if you wish to explore the countryside or visit vineyards at your own pace. Do remember that driving in Italy requires an International Driving Permit along with your regular driver’s license for non-EU citizens. Also, many city centers in Tuscany are limited traffic zones (ZTLs) and are camera-controlled. Driving into these zones without a permit will result in a fine.

Taxis are readily available in cities and larger towns. Uber operates in Florence and is another convenient option for getting around.

Best Time to Visit: Tuscany is a year-round destination, but the ideal times to visit are between April and June, and September and October when the weather is comfortable and the countryside is at its most vibrant.

Language: Italian is the official language. However, English is widely spoken in tourist areas, hotels, and restaurants.

Currency: Euro (€) is the official currency of Italy.

Safety: Tuscany is generally safe for tourists, but like any other tourist destination, be aware of your surroundings, particularly in crowded places.

Electricity: Italy operates on a 220V supply voltage and 50Hz. The power plugs and sockets are of type F and L.

Cities, Towns and Villages within Tuscany

As the capital of Tuscany, Florence is an incredible mix of art, history, and culture. It’s the birthplace of the Renaissance, and home to world-class museums such as the Uffizi Gallery and the Accademia Gallery, where you can admire Michelangelo’s David. The city also has a rich culinary scene, with countless trattorias serving classic Tuscan cuisine. Florence is an ideal base for day trips throughout the region, thanks to its central location and excellent transportation links.

Famous for its medieval cityscape and the historic Palio horse race, Siena is a must-visit. The city’s heart is the Piazza del Campo, a shell-shaped square that hosts the Palio twice every summer. The Siena Cathedral (Duomo di Siena) is another highlight, featuring intricate Gothic architecture. Siena’s historical center has been declared a UNESCO World Heritage Site for its preserved medieval city planning and architectural splendor.

RELATED: Top Small Towns in Italy to Visit Famous for Wine [Wineries & Wine Tour Options Included]

Known worldwide for its leaning tower, Pisa has much more to offer. The city hosts a wealth of historic sites, including the Piazza dei Miracoli, where you’ll find the Leaning Tower, the Pisa Cathedral, and the Baptistery. For an authentic Tuscan experience, visit during June when the city celebrates the Luminara di San Ranieri festival with thousands of candles lighting up the riverside.

Enclosed by well-preserved Renaissance walls, Lucca is a charming town ideal for leisurely exploration. Its cobblestone streets, beautiful piazzas, and numerous churches, including the Lucca Cathedral, offer a snapshot of its rich history. One fun fact is that the town’s intact city walls have been transformed into a pedestrian promenade, perfect for biking or a leisurely walk.

San Gimignano

Known as the “Town of Fine Towers”, San Gimignano is famed for its 14 medieval towers that dominate the skyline. This UNESCO World Heritage Site offers fantastic art, great dining, and world-class gelato at the Gelateria Dondoli, a two-time champion of the Gelato World Cup. Its proximity to Chianti makes it an excellent stop on a Tuscan wine tour.

Montepulciano

This medieval and Renaissance hill town is known for its Vino Nobile wines. Stroll along the Corso, a grand avenue packed with Renaissance palazzi and churches, or visit the impressive Tempio di San Biagio. The town also offers panoramic views over the surrounding vineyards and Val d’Orcia.

Best known for its Brunello di Montalcino wines, this hilltop town is a favorite among wine lovers. Besides its wine, the town boasts a stunning fortress offering panoramic views, a charming historical center, and the beautiful Romanesque Abbey of Sant’Antimo.

RELATED: Read Recent Articles and Travel Guides for Exploring Italy

A true hidden gem, Volterra offers Etruscan, Roman, and medieval sites, including the Roman Theatre and the Etruscan Acropolis. Volterra is also renowned for its alabaster craftsmanship, a tradition that dates back to the Etruscan period.

Set on a hill overlooking Lake Trasimeno, Cortona is one of Tuscany’s oldest towns with a history dating back to the Etruscans. Visit the Museo dell’Accademia Etrusca, or explore the town’s charming narrow streets and squares. The town is also known from the book and movie “Under the Tuscan Sun.”

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Frequently Asked Questions about Wine Tours in Tuscany

What kinds of tuscany wine tours and wine tasting experiences are there.

Tuscany offers a rich variety of wine tours and tastings that cater to all tastes and preferences. For instance, there are full day private tours from Florence, led by a knowledgeable sommelier, offering the chance to visit three different wineries and enjoy an authentic Tuscan lunch. For those looking to combine scenic drives with wine, consider the excursion that pairs a Fiat 500 tour with a visit to a 15th-century wine estate. Alternatively, you can delve into Siena’s surrounding vineyards on a small group tasting tour that educates your palate with the help of a sommelier. For those seeking a unique countryside experience, a horseback riding tour in the Tuscan countryside lets you unwind at a country resort with a full Tuscan lunch and local Chianti wine. These are just a few examples of the range of experiences Tuscany has to offer. Each tour provides a unique way to explore the region’s world-renowned wine culture. To learn more and book a wine tour that suits your preference, please check our detailed guide.

When is the best time of year for a wine tour in Tuscany?

The best time to visit Tuscany for a wine tour largely depends on your personal preferences, but there are a few peak periods that are particularly popular. Spring (April to June) and Fall (September and October) are often considered the ideal times for a Tuscan wine tour. The weather during these seasons is typically mild and pleasant, and the landscape is at its most vibrant – with blooming flowers in spring, and changing leaves in the fall. Fall is also the time of the grape harvest (known as “vendemmia”), which can be a fascinating process to witness. Some wineries even allow visitors to participate in the harvest. Summer (July and August) in Tuscany can be quite hot, and many Italians go on vacation in August, which means some wineries might be closed. However, the region is still beautiful during this time and the wine tours are certainly still operational. Winter (November to March) is the low tourist season in Tuscany. While the weather can be cooler and wetter, there are fewer tourists, making it a good time to visit if you prefer to avoid crowds. Regardless of when you choose to visit, it’s always a good idea to check with individual wineries or tour companies in advance for their operating hours and to book your tour.

What is the main wine region in Tuscany?

The most renowned wine region in Tuscany is the Chianti region, famous for producing Chianti and Chianti Classico wines. It’s characterized by its idyllic rolling hills, historic vineyards, and scenic villages. The Chianti region is situated between Florence and Siena, making it conveniently accessible for tourists and wine lovers. However, Tuscany boasts several other notable wine-producing areas. For example, Montalcino, located south of the Chianti region, is renowned for its Brunello di Montalcino wines. Nearby, Montepulciano produces the famous Vino Nobile di Montepulciano. Further west towards the coast, you’ll find the Bolgheri region, known for its superb “Super Tuscan” wines, a term referring to high-quality wines that don’t adhere to traditional Italian wine regulations but have nonetheless achieved worldwide recognition. Each of these areas offers unique variations in climate, soil, and winemaking traditions, contributing to the diversity and richness of Tuscan wines.

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How to Plan an Incredible 7 Day Tuscany Itinerary

Want to plan an incredible trip to Tuscany, but not sure where to start, what to include, or how much time you need? In this guide, we’re going to cover exactly how to spend 7 days in Tuscany. 

Tuscany is an incredible – albeit very popular – slice of Italy. Within its borders, which stretch almost coast to coast in Central Italy, you’ll find world-class wine (several of Italy’s most prestigious reds come from Tuscany), picturesque landscapes (that are surprisingly diverse), amazing food, and countless charming hilltop towns with commanding views over said landscapes. 

Before my (Matt here!) last trip to Italy, I had never explored much of Tuscany outside of Florence. While Florence is great, especially if you’re into history and art, the real magic of Tuscany happens out in the countryside. 

If it’s your first time in Tuscany, you should plan on balancing your trip between the hustle and bustle of cities like Florence and Siena, and the slower life found in the Val d’Orcia and Volterra. 

In this guide, we’re going to cover everything you need to know to plan an incredible Tuscany road trip (spoiler: you’re probably going to want to rent a car).

We’ll start with some important logistics to help you structure your itinerary, then dive into the best things to do and see in Tuscany based on our experience. 

The intention here is to give you the information you need to plan your own trip to Tuscany. 

Keep in mind that we’re assuming you have one week in Tuscany in the main itinerary. If you have more or less time than that, we’ve got a section below the main itinerary with suggestions on what to do with more and less time (3-5 days, or 10+ days). 

Disclaimer: Some of the links in this post, like hotel links, are affiliate links, meaning at no additional cost to you, we make a little bit of money if you click through and book. That being said, we would never recommend something to you that we don’t stand behind 100%.

A Quick Tuscany Geography Overview

Before we get into the meat of the itinerary, it makes sense to take a second to talk about the geography of Italy’s most famous region. 

Tuscany is in central Italy and is a land of olive trees as far as the eye can see, rolling hills, winding roads, and cypress trees.

The capital of Tuscany is Florence, which is well worth a couple of days exploring (our recommendation would be to do it at the end of your trip), but cities like Pisa and Siena are also within Tuscany’s boundaries. 

In order to talk about what to focus your time on when you visit Tuscany, we’re going to break up the region into four distinct areas. This is just our way of breaking things down into more digestible pieces, it’s not an official designation or anything like that. 

Here are those four regions: 

• Florence & Around (including Chianti)
• Siena & Around
• Southern Tuscany & The Val d’Orcia (Pienza and Montepulciano)
• San Gimignano and Volterra

Now, there are other places in Tuscany – like Pisa and Lucca up north, and the Tuscan coast out to the west – but if you have limited time and you’re looking for the quintessential Tuscan countryside, these are the four areas we think you want to focus on if you have 10 days or less (which is going to be most people reading this). 

With that brief and incomplete overview out of the way, let’s get into the information you’ll need to actually plan your trip to Tuscany. 

Do You Need a Car for This Itinerary?

While we’re big fans of train travel in Italy, Tuscany is one of the places (along with Sicily ) where you really need a car to fully experience it. 

You’ll need to rent a car, and we’d strongly recommend you avoid having a car for your time in Florence (if you decide to include the biggest city in Tuscany in your itinerary). Parking in Florence will be expensive and unnecessary – you really don’t need a car. 

To pull this off, we’d put Florence at the end of your time in Tuscany. 

You’ll want to rent a car from the airport when you arrive and head straight down to Siena, and then drop it off on the day you ARRIVE back in Florence (day 6, if you follow our itinerary below).

Then take the bus from the Florence Airport into the city, and spend a couple of days exploring before you head home!

That way, you don’t have to deal with traffic or parking in Florence, which can be a nightmare. 

Here are a few things to know about renting a car in Italy (keep in mind that we’re American).

You Need an International Drivers License if You’re Coming From the US

You can get them at AAA in the US. While they might not ask you for it at the rental car counter, the police will ask you for it if you get into an accident or get pulled over. Best not to risk it. 

Know Your Toll Roads

Toll roads in Italy – called Autostrade – are essentially equivalent to Interstates here in the United States. 

They have anywhere from two to four lanes, high speed limits, and are more or less a straight shot between destinations. You can only enter and exit them at fixed points, but there are gas stations and casual restaurants at rest stops along the way. 

Unlike here in the US, you have to pay to use the highways, which are toll roads. 

You do this by either renting a transponder from your car rental company, or by stopping at one of the entrance stations and getting a ticket, which you pay when you exit the toll road. You can almost always pay with a credit card these days (in our experience, anyway). 

Here’s a guide to help you understand toll roads in Italy .

What If You Don’t Want to Drive in Tuscany?

Look, we totally understand the hesitance to drive in a foreign country. Especially in a country like Italy, which doesn’t exactly have a reputation for having friendly, patient drivers. 

If you don’t want to drive in Italy (or can’t drive in Italy), you can still make this itinerary work using a combination of public transportation and guided tours. 

You’ll want to base yourself in Florence and Siena – which are connected by train and bus, so they’re relatively easy to get between – and use them as a home base to do day trips out into the wider Tuscan countryside. 

Unfortunately, that means you’re going to be paying more for guided tours to the Val d’Orcia and San Gimignano, and you’ll have less flexibility to explore at your own pace without a car. 

Where to Start and End Your Road Trip

Without a doubt, the best place to start and end this road trip is going to be Florence. There are three main reasons why we think that’s the case. 

First, if you’re flying in from outside of Italy, Florence is your best bet in terms of finding flights. You’ll want to fly into Florence Airport (FLR), NOT PISA INTERNATIONAL AIRPORT, which as you might expect, is actually in Pisa (about 45 minutes west of Florence). 

Second, you’ll have the best selection of rental cars in Florence.

Third, Florence is the closest major city (with a solid airport) to the main regions of Tuscany we touched on above. It’ll take about an hour and 15 minutes to get from Florence to Siena, your first stop on this itinerary. 

Another airport to look at – and this is actually the airport we flew into – is Bologna Guglielmo Marconi Airport (BLQ) . It’s about 45 minutes north of Florence (which means 2 hours to Siena), but it’s a good alternative and you might be able to find slightly cheaper rental cars and flights. 

Plus, we adore Bologna, and it’s worth a day or two of your time (here’s our guide to spending one day in Bologna). 

Plan on doing a big loop through Tuscany, and returning your car to (and flying out of, if applicable) the same airport you came in to. 

Is One Week Enough Time?

While you could technically do Tuscany in a couple of days, you’re not going to have much time to experience the dolce vita that makes this part of Italy special if you do it that way. 

We think you need at least one week to do all four of the regions of Tuscany we mentioned above.

That will give you enough time to get beyond the surface level in each place. That’s why we chose to write this guide for 7 days in Tuscany. 

A good example of why this is important is Siena. Siena is a madhouse during the day when buses full of tourists get dropped off to wander through Piazza del Campo and the Duomo. 

However, when those tour buses leave, Siena transforms into a much more serene destination – the narrow alleys go from packed wall-to-wall with people to being nearly deserted. 

If you only have a couple of days in Tuscany, you won’t have the time to experience Siena either in the early morning or evening, when it’s a completely different – and much more pleasant – place. 

What should you do if you only have 3-5 days or so? Pick one or two of the regions above, and focus on those rather than trying to do it all.

We have suggestions on how to plan a shorter itinerary below the main itinerary, which includes day-by-day itinerary options for 3 and 5 days.  

More time? Great! We also have suggestions on what to do with your extra time in a section below the main itinerary. 

Where to Stay in Tuscany

When it comes to where to stay, there are essentially three approaches you could take: stay in one place for your entire trip, and use it as a base for exploring the entire region, stay in a different place each night, or a find a home base in each micro-region and stay there for a couple of nights each. 

As you might imagine, we like the last approach, which is a hybrid that gives you the benefits of staying in each of the parts of Tuscany that you’re visiting (which cuts down on drive time) and not having to move around every single night. 

If you follow our itinerary below as written, you’ll stay in Florence, Siena, and the Val d’Orcia for 2-3 nights each. 

By the way, we have an entire guide dedicated to helping you find the perfect place to stay in Tuscany . If you want more detail, head over and read that.

Hotels in the City Center vs. Agriturismos?

The next decision you’ll need to make is what kind of stay you’re looking for. Do you want to stay right in the middle of all the action in a hotel right in the city center, or would you rather have a tranquil stay in the Tuscan countryside?

Our (strong) bias is the latter – we stayed exclusively at Agriturismos in Tuscany, and loved every second of it . 

You won’t have to worry about (or pay for) overnight parking, you’ll have a little more space (if you’re lucky, a patio with some nice views), and you’ll be awash in the warm glow of the dolce vita as you sip your morning coffee on the outdoor patio with a view of Cypress Trees and hilltop towns. 

The upside of staying in the center of a city is, obviously, convenience. However, parking and navigating ZTL (the car-free zones in the city center of most of Tuscany’s towns and cities) make staying in a city with a car less appealing, at least in our estimation. 

Our recommendation would be to spend your two nights in Florence in the city center (you won’t have a car at this point, so parking isn’t as much of an issue), and stay in the countryside around Siena and in the Val d’Orcia . 

Where to Stay in Florence, Siena, and the Val d’Orcia

Let’s quickly cover some of our specific recommendations on where to stay based on our own experience and research. 

In Siena, we stayed at Il Palazzetto just outside of town for a few nights and loved enjoying our coffee in the morning with a view of Tuscany from our front porch.

It’s a farmhouse in the countryside surrounded by olive trees, rolling hills, and Cypress trees, and they have a few beautiful rooms and apartments on the property. Very friendly staff, and helpful recommendations for what to do, see, and eat in Siena. 

In the Val d’Orcia, we stayed at Agriturismo Il Casalino , a cute little farmhouse in the valley below Pienza with a spectacular view of Pienza up on the hill. Very friendly owner, and the location is truly excellent. Cypress trees and rolling hills as far as the eye can see!

In Florence, you’re going to want to stay in the city center. We’ve stayed at Pietrapiana Boutique Apartments , which are in a great central location about ten minutes from the Duomo di Firenze. They’re compact, but they have a little more space to spread out and relax.

Here’s our guide to where to stay in Florence for more detail. 

7 Days in Tuscany: How to Plan an Amazing Tuscany Road Trip

With a week, we’d strongly recommend limiting your trip to Florence, Siena, the Val d’Orcia, and San Gimignano (plus a side trip to Volterra) to avoid driving for hours a day and, most importantly, missing out on the slow life that makes this part of Italy special.

We’ve structured this itinerary as a loop that begins and ends in Florence, like we mentioned above. 

Now, let’s get into the itinerary itself! Here’s a day-by-day itinerary, and a map to visualize what it looks like. 

• Day 1: Siena
• Day 2: Siena
• Day 3: Val d’Orcia
• Day 4: Val d’Orcia
• Day 5: San Gimignano and Volterra (end in Florence)
• Day 6: Florence
• Day 7: Florence

Now that you’ve got a good overview of the geography and logistics, let’s get into exactly how to spend one week exploring the best of Tuscany!

Days 1 & 2: Siena

Drive Time and Distance from Florence to Siena: 1 hour 15 minutes / 78 km 

On your first day, pick up your car and head straight to Siena. Chances are, you’re either taking the train to Florence, or you’re flying into the airport in Florence.

Either way, skip Florence for now (you’ll be back!) and head straight down to Siena, which will take you about 90 minutes, depending on traffic. 

There’s really no place to soak up Tuscany’s medieval charm quite like the hilltop city of Siena, one of the best preserved medieval villages in all of Italy.

The striking city is characterized by its red clay brick houses, grand Gothic churches and palaces, and soaring medieval towers. It’s home to some of the finest art and architecture in the country thanks to its great wealth and power during the 13th and 14th centuries.

Siena is also famous for its historic Palio horse race, which takes place on July 2nd and August 16th each year. The event has been taking place in the city since the 15th century and features 10 riders from different districts racing bareback around central Piazza del Campo. 

This is one of the most exciting – albeit extremely busy and expensive – times to visit.

Things to Do in Siena

Siena’s distinctive medieval architecture and unique charm have earned the city the recognition of UNESCO World Heritage Site. And it is now one of the most popular destinations in Tuscany.

This does, however, mean that it gets pretty busy all throughout the year, with crowds that rival even the bigger cities of Florence and Pisa.

There’s one implication of Siena’s popularity that you should consider. 

Many people visit Siena on a day trip from Florence , which means it’s at its busiest in the middle of the day.

To see the city at its most peaceful, head out early in the morning or late in the evening and enjoy having space to yourself. This is why we’ve recommended spending two days in Siena.

• A Walking Tour of Siena. We did this walking tour on our first day and it was an excellent introduction to the history and culture of Siena. It even included a visit to the cathedral, which is a fascinating place to explore with a knowledgeable local guide who can point things out that you wouldn’t otherwise notice (though, it does not include a ticket to the viewpoint of the cathedral – more on that in a second). 
• Piazza Del Campo. Siena’s impressive main square is surrounded by stunning Medieval palaces and historic buildings. Today, it’s a hub of social life in the city and a great place to take a stroll or stop for a drink on the terrace of one of the charming cafes.
• The Duomo di Siena (and the view from Facciatone). Siena’s 13th-century cathedral is one of the finest Gothic churches in all of Italy, with an intricate marble façade and lavishly decorated interiors. The colorful stained-glass window and amazing mosaic floors were particular highlights for us. Plus the Panorama dal Facciatone – located at the top of the incomplete expansion of the church in the now museum – offers breathtaking views over the historic city. The extra cost (you have to buy a special ticket) to get up to the viewpoint is well worth it, we think. 
• Eating and Drinking in Siena. Siena is a great foodie destination, with plenty of delicious things to try. Places we’d recommend eating and drinking in Siena are Bakery Il Magnifico (for Siena’s famous chewy almond cookies, Ricciarelli), Caffetteria Torrefazione Fiorella (for coffee at the counter), Du’ Cose Da Berna (recommended by the host at our agriturismo), and La Prosciutteria Crudi e Bollicine Siena (for cured meats).

Days 3 & 4: The Val d’Orcia (Montalcino, Montepulciano, & Pienza)

Drive Time and Distance from Siena to Val d’Orcia: 1 hour 15 minutes / 55 km

Next, it’s time to journey through the beautiful Val d’Orcia in southern Tuscany. This is one of our absolute favorite parts of the region. 

If you’re like us, the things you associate with Tuscany from popular culture are rolling hills, cypress trees, and red wines. Which, spoiler alert, is exactly what you’re going to find in Tuscany (along with some other gems). 

The journey from Siena to the Val d’Orcia can take anywhere between 1 hour and 1 hour 15 minutes, depending on the route and traffic.

The Val d’Orcia is quintessential Tuscany, with rolling green hills (at least in the spring and early summer before they turn brown) dotted with cypress trees, vineyards, historic farmhouses, and picturesque hilltop towns.

The valley’s gorgeous landscapes and unmatched beauty inspired many Renaissance painters during the 15th and 16th centuries.

Two days is a good amount of time to spend on a little road trip around the Val d’Orcia. We’d suggest focusing your visit on three main towns; Montepulciano, Montalcino, and Pienza. 

Things to Do in the Val d’Orcia

Pienza is situated in the middle of the two other towns. We’d recommend starting at Montepulciano or Montalcino on your first day and moving east or west with Pienza as the second stop to minimize travel time. 

There are also tons of great places to stay in and around Pienza (for what it’s worth, we chose Agriturismo Il Casalino and loved it) so it makes a good base in the region.

The other thing to know is that each of the towns are fairly small, so you’ll only need a couple of hours to explore the town itself. You can spend the rest of your time enjoying a long leisurely lunch, sipping local wine with a view, and driving the winding roads through the countryside.

Montepulciano

This quaint little town sits on the edge of a volcanic rock cliff face with sweeping views over the surrounding valley.

Make sure to go wine tasting at De’ Ricci (Vino Nobile is the local red wine), climb the tower of Comune di Montepulciano for excellent views of the valley sprawling out to the west, and take a stroll along the winding Via di Gracciano nel Corso, the main street in town.

Sitting in the heart of Tuscany’s famous Brunello wine region, Montalcino is a must-visit for red wine lovers.

You can sample local Brunello wine at Ciacci Piccolomini D’Aragona (or any of the other wineries south of Montalcino) where we got a crash course in Brunello, which is largely made with the same grape varietals as Chianti, but is processed differently.

You should also take the time to walk the historic walls of Fortezza di Montalcino, the town’s medieval fortress, and visit the Romanesque monastery Abbazia di Sant’Antimo (which is conveniently right next to the winery we recommended above, which makes it an easy stop). 

A romantic Renaissance town with spectacular panoramic views over the surrounding countryside. This viewpoint was our favorite.

The town is also famous for its local Pecorino di Pienza cheese, which you can try at La Taverna del Pecorino (if you can find it, get it baked with honey on top – pecorino con miele).

And don’t miss coffee with a view at the lovely Bar il Casello .

Day 5: San Gimignano, Volterra, & Drive to Florence

Drive Time and Distance from Val d’Orcia to San Gimignano: 1 hour 45 minutes / 95 km

On day five, you’ll want to gradually make your way back from the Val d’Orcia towards Florence, taking a slight detour to visit the towns of San Gimignano and Volterra along the way.

Both towns sit on the western end of Tuscany towards the sea. They are located around 30km from each other and can take anywhere between 40 minutes to 1 hour to drive between. So be sure to factor this into your day if you do want to visit both.

San Gimignano is a lovely medieval town and another of Tuscany’s UNESCO World Heritage sites. The small town once had over 70 soaring medieval towers making up its skyline, gaining it the unique title of the “Manhattan of the Middle Ages”. 

Today only a handful of these towers remain, but the town is still known as Italy’s “City of Towers”. 

Nearby Volterra is slightly less well-known than its famous neighbor (unless you’re a Twilight fan, in which case you probably know it). 

The less popular walled hilltop town is still a great place to explore and is worth the drive, with several important historic and archeological sites including a world-class Etruscan museum and a couple of Roman archaeological sites. 

You’ll also find considerably smaller crowds than San Gimignano, so it’s a good place to escape the chaos for a couple of hours.

Things to Do in San Gimignano

San Gimignano is a relatively compact town, and it is one of the most popular places to visit in Tuscany.

Wandering the narrow streets, you’ll likely find yourself packed wall-to-wall with other visitors if you’re here in the summer between 11:00 am and 5:00 pm (especially on a weekend).

However, it’s easy to see why so many visitors flock here – the towers of San Gimignano are an iconic piece of Tuscany’s landscape.

• Eating in San Gimignano. San Gimignano is a lovely spot to make the most of Tuscany’s world-class cuisine. Enjoy lunch on the terrace at Le Vecchie Mura for great food and even better views. And don’t forget to grab some tasty gelato from Gelateria Dondoli (they also have gelato making classes). 
• Drink Vernaccia Di San Gimignano. Produced in the vineyards surrounding the town, Vernaccia is Tuscany’s most famous white wine. You can sample Vernaccia in most restaurants and bars around town, or head to the Vernaccia di San Gimignano Wine Experience to learn more.
• Climb the Torre Grossa. The bell tower of the Palazzo Communale (town hall) is the tallest remaining tower in San Gimignano, sitting at 177 feet. You can climb 218 steps to reach the tower’s summit and enjoy beautiful views over the town. And while you’re there, spend 15 minutes admiring the artwork in the attached Palazzo Comunale – there’s not much but it’s definitely worth a quick visit.
• Parco della Rocca. This lovely hilltop park is the highest point in San Gimignano and is home to the ruins of a medieval fortress. Today it’s a great place to take a walk or stop for a relaxing picnic with amazing views over the town (the best view is from here ).

Things to Do in Volterra

Volterra is also a small town at the top of a rocky outcropping (are you seeing the pattern here yet?) with great views out over Tuscany (and even out to the sea, on a clear day).

There’s not a whole lot to do in town, and we found it to be pretty sleepy on a random weekday afternoon in mid-October. 

However, it’s gorgeous and is an important piece of history on the Italian Peninsula. It’s worth visiting for the walking tour and Etruscan Museum alone. 

An afternoon in Volterra is well worth the drive from San Gimignano, we think. You only need about a half a day to see the highlights. Here are some of our favorite things to do in Volterra.

• The Etruscan Museum. Volterra has been home to many different inhabitants over the years (it has been consistently inhabited since the 8th Century B.C.), including the Etruscans, who left their mark on the city. The Etruscan Museum in town is well worth a couple of hours of your time – it has one of the most extensive collections of Etruscan artifacts in the world. 
• Walking Tour. This twilight walking tour of Volterra (NOT THAT TWILIGHT) was one of our favorite experiences in all of Tuscany. It covered the history of the city in just one hour. The time of the tour varies each day, and it is well worth the small donation (only cash) to hear about Volterra’s history from a local, including the feat of saving the main gate into town from destruction during World War 2. 
• Roman Ruins. One of the other fascinating elements at play here is related to another of the town’s inhabitants over the millenia, the Romans. There are several sites around town where excavations have uncovered extensive Roman ruins, and the best example is the Roman Theater on the northern side of town ( here is the best view). There is another, more recently uncovered Roman amphitheater further north outside of town, which was uncovered in the 2000’s (which is the most recent archaeological discovery I personally had ever heard of). 

Days 6 & 7: Florence

Drive Time and Distance from Volterra to Florence: 1 hour 30 minutes / 85 km

Finally, spend the last two days of your trip exploring the regional capital and one of Italy’s most famous cities, Florence.

The city was one of the richest and most powerful in all of Europe (if not the world) during the 15th century, explaining its unmatched elegance and grandeur today.

Known as the ‘Birthplace of Renaissance’, Florence is a hub of world-class art and architecture.

Its two impressive art galleries are home to more masterpieces than you can possibly fathom, while the city itself is one giant open-air museum, with exquisite churches and grand Renaissance palaces on every corner.

It’s difficult not to fall in love with Florence, despite the huge tourist crowds that descend on the Italian city all year round.

Things to Do in Florence

Florence may be relatively small as far as Italian cities go, but it certainly still packs a good punch when it comes to things to see and do.

Two days is just about enough time to experience the city’s top sites and visit the two main galleries.

However, try to avoid visiting the Uffizi Gallery and Galleria dell’Accademia on the same day. Even for the biggest art lover, it’s simply too much information to digest all at once.

• Piazza del Duomo & Climbing the Dome. Sitting at the heart of the city, Piazza del Duomo is home to many of Florence’s most important landmarks, including the 13th-century Cathedral and its famous dome, the Baptistery, and Giotto’s Bell Tower. With only two days, we’d prioritize Brunelleschi’s Dome. By climbing 463 steps to the top of the iconic dome, you can admire the striking frescoes up close and experience amazing views over the church’s beautiful interior. Try to do it first thing in the morning for the fewest people, and book in advance here . 
• The Uffizi Gallery. This world-class gallery has a whopping 101 rooms that hold an unparalleled collection of Renaissance and European art. Many of the artworks were assembled by the powerful Medici family between the 15th-18th centuries. We’d highly recommend visiting on a guided tour to add context and richness to your visit – it can be a little overwhelming otherwise. We did this tour and absolutely loved our experience!
• The Galleria dell’Accademia and the David. Florence’s second major gallery is best known for one particular piece, Michaelangelo’s Statue of David, which is one of the most famous sculptures in the world. It’s worth visiting the gallery on a guided tour ( this is the one I did on my latest visit to Florence with my mom, who had never seen David in person before) to learn more about the famous statue and other artworks in the gallery.
• Explore Oltrarno. Just across Ponte Vecchio, which crosses over the Arno River that runs through Florence’s historic center, is one of our favorite parts of the city, Oltrarno. The neighborhood is full of charming little piazzas, traditional restaurants, and cozy bars. It’s a great place for a peaceful stroll or an afternoon aperitif. Check out Le Volpi e l’Uva for the best Italian wine selection, and Gelateria Della Passera for Alysha’s favorite gelato in Florence.
• Eating and Drinking in Florence. Tuscany is a region that’s known for its fantastic cuisine, and you can sample the best of it in its capital city of Florence. Start your mornings with coffee from Coffee Mantra , indulge in delicious pizza from award-winning Ciro and Sons , and don’t miss the Pappardelle al Cinghiale (pasta and wild boar ragu) at Da Garibardi . The city also has two food markets, Centrale and Sant’Ambrogio, which are must-visits for foodies.

More Time? Here’s What We’d Add to Your Itinerary

There are two places that we really liked that you’re missing if you follow the itinerary above as written. They are Chianti and Lucca, which are west of the majority of this itinerary. 

With a few extra days, we’d spend a day or two in each place. Both areas can easily be covered in a day for each, but two gives you the opportunity to do things at a more leisurely pace. You can absolutely do Chianti as a half day trip, either from Siena or Florence. 

You’ll notice that we haven’t included Pisa here, which is in the same vicinity as Lucca. We MUCH prefer Lucca to Pisa, both because it’s a more interesting city in general, and because it sees a fraction of the tourists that Pisa does. 

If you absolutely must see the leaning tower of Pisa, then we’d add it as a day trip from Lucca (but we wouldn’t stay the night in Pisa, if you can avoid it). 

Lucca is one of our favorite discoveries from our six week Italy trip in 2021, and the highlight here is the intact city walls that date back to the Renaissance. You can circumnavigate the city by walking along the walls, which is absolutely something you should plan on doing. 

The city is in a narrow valley, surrounded by mountains on the south and north sides. One thing you should absolutely do in Lucca is climb one of the many towers in the center of town.

We climbed the Torre Guinigi , and the view from the top with the towers and churches of Lucca and the surrounding mountainous landscape was sublime. 

Another thing not to miss is Piazza dell’Anfiteatro , which is a piazza built on the site of a former Roman amphitheater. The piazza keeps the same oval shape today, though the restaurants on it leave a bit to be desired.  

Chianti is a wine region just south of the city of Florence that is known for its red wines, specifically the Chianti Classico, which is one of the main wine exports of Tuscany. 

Similar to other Italian D.O.C.G. wines like Prosecco and Brunello, Chianti Classico is a red wine that is made in a specific way with primarily Sangiovese grapes from the Chianti region.

It is one of the most famous wines that comes out of Italy. If you don’t like red wine, I have some bad news for you – Tuscany is all about the red wines (except for vernaccia, which is a white wine that comes from San Gimignano!). 

As you might imagine, Chianti is all about the wine tasting. Now, on the itinerary above, you’ve covered a few different famous red wines from Tuscany like Brunello and Rosso di Montepulciano, and Chianti is somewhere in between the two in terms of prestige and price. 

The best way to experience the wines of Chianti is on a wine tour. In terms of guided tours, you have two options. You can either choose a tour that goes deep on a single winery , usually including a cellar tour and detailed tasting (but you’ll have to make your way out to the winery), or a tour that takes you around to multiple wineries . 

Since you have a car, we’d recommend the first option, which gives you a deeper, more intimate experience. We did this wine tour of a tiny organic winery in Chianti and absolutely loved it. 

If you have the time, we’d also recommend a stop at the lovely town of Badia a Passignano, a charming little town in the heart of Chianti. 

Pro tip: If you’re buying Chianti Classico at home or somewhere else in Italy, make sure it says “Chianti Classico” (versus just “Chianti”, which we learned can be made elsewhere in Tuscany) and has a rooster logo somewhere on the bottle, which is how you know it’s legit. 

Planning a Shorter Itinerary (3-5 Days)

If you have fewer than 7 days in Tuscany, our recommendation would be to focus your time on specific regions within Tuscany (see the geography overview above for how we’d break it up) rather than trying to see it all. 

The first thing to consider is whether or not you want to include Florence in your itinerary. You might have already been there, or you might be more interested in the charming hilltop towns in the south of Tuscany. 

If you want to include Florence in your itinerary AND you have limited time , we’d recommend basing yourself in Florence, and doing a day trip to Siena, Lucca, or Chianti from there. In this scenario, we’d strongly recommend that you don’t rent a car! 

We actually have a 3 day Florence itinerary for you to basically steal, which includes a day trip on the third day out into broader Tuscany. 

If you have three days and you don’t want to include Florence , then we’d focus on one region (and we’d make it either Siena or the Val d’Orcia).

If you have five days or so , focus on two regions – Siena and the Val d’Orcia. 

You could also structure your own itinerary based on your particular interests by using the information in the main itinerary above!

5 Days in Tuscany: Siena and the Val d’Orcia

These two regions are quintessential Tuscany, at least for us. Tuscany is famous for many things, but somewhere near the top of the list has to be cypress trees and hilltop towns perched atop rolling hills as far as the eye can see. 

That’s what you’ll find between Siena and the Val d’Orcia. If you only have five days, we’d split it between these two regions and completely skip Florence and San Gimignano. 

Here’s what that itinerary looks like: 

• Day 1: Drive to Siena
• Day 2: Siena + Monteriggioni
• Day 3: Val d’Orcia (Montalcino)
• Day 4: Val d’Orcia (Pienza & Montepulciano)
• Day 5: Val d’Orcia & Drive to Florence

3 Days in Tuscany: Siena & Around

Siena is a great city, and like we mentioned above is probably the best example of a charming hill town in Tuscany. It’s a bigger city than the vast majority of the other smaller towns on this itinerary, and it’s just beautiful vista after beautiful vista around every corner. 

If you have three days in Tuscany, Siena makes for a great home base because it’s central to both San Gimignano and the Val d’Orcia, which makes a day trip more feasible. 

One idea for a shorter itinerary like this that is based in Siena would be to hop on a day trip from Siena to reach either San Gimignano or the Val d’Orcia.

The tradeoff of seeing one of those places is that it gives you less time to explore Siena (you really only need about a day and a half, we think). 

• Day 1: Arrive in Siena
• Day 2: Day Trip from Siena
• Day 3: Siena + Drive to Florence

In terms of the day trips, we’d definitely recommend going with the company behind the walking tour we did in Siena, which we enjoyed. They have a small group tour to the Val d’Orcia (Montepulciano and Pienza) and one that goes west to San Gimignano and Volterra . 

3 Days in Tuscany: The Val d’Orcia

As we have already covered multiple times, we love the Val d’Orcia. 

The only issue with the Val d’Orcia is that it’s a little far from Florence, which means you’re going to spend a lot of time in the car between the two (roughly 90 minutes each way) for just a couple of days spent there. 

Still, we think it’s worth it. This is by far our favorite part of Tuscany.  

• Day 1: Drive to the Val d’Orcia + Montalcino
• Day 2: Pienza & Montepulciano)
• Day 3: Morning Scenic Drive + Drive Back

Matt is the founder and main writer behind Wheatless Wanderlust, which he started back in 2018 as a way to share his gluten free travel guides with his fellow Celiac travelers.

Since then, Matt and his wife Alysha have visited 18 national parks, spent three months in Europe and six weeks in Colombia, and have explored every corner of the Pacific Northwest, which is where Matt grew up.

He writes super detailed guides to the places they visit, bringing together personal experience and historical context to help YOU plan an amazing trip.

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Tuscany Day Trip from Florence with Chianti, Siena & San Gimignano

• World-famous for its hillside towns, sweeping views, cuisine, and wine, there are endless reasons to visit Tuscany. Experience all of these in the most authentic, relaxed way possible on this meticulously planned Tuscany day trip from Florence. Take the hassle out of your visit so you can sit back, relax, and enjoy a glass of wine (or two).
• Travel through Tuscany to Siena, Chianti, and San Gimignano in a small luxury vehicle with no more than 14 others.
• Stroll the beautiful medieval town of Siena, see its cathedral and the location of the Palio, and wander its atmospheric streets.
• Sit down for a relaxing lunch and wine tasting at an authentic Chianti farmhouse and vineyard.
• Explore one of Tuscany’s gems—the town of San Gimignano, a UNESCO World Heritage site—with a knowledgeable guide.
• Relax knowing that your two experts, a professional driver and local guide, have all the logistics handled for a perfect day in Italy.

Tour description

Discover three stunning destinations on a perfectly planned tuscany day trip from florence..

In just one day, you'll see, taste, and experience the best of Tuscany, complete with a homemade locally sourced lunch and expert-led wine tasting at a family-run farm in Chianti. We'll whisk you away to Siena and San Gimignano, two of the most stunning towns in Tuscany, helping you experience as much of this storied region as possible without you having to worry about the logistics. With a knowledgeable guide to lead the way as well as an experienced driver to get you from place to place, we've got all the details handled for an unforgettable Tuscany day trip from Florence.

See the best of Siena with the guidance of an expert in all things Tuscany.

Our day trip to Tuscany starts in the center of Florence, where you'll meet your expert guide, dedicated driver, and small group before boarding a comfortable, air-conditioned luxury vehicle. But before we set off into the rolling hills of Tuscany, we'll make a stop at Florence's best panoramic viewpoint for photos.

Your next stop will be eclectic, iconic Siena, which was miraculously spared from bombing during WWII—making it a pristine medieval gem in the midst of the Tuscan region. Stroll through the historic streets of the city center while your guide points out the most notable landmarks, including the famed Siena Cathedral and the location of the biannual Palio horserace.

Enjoy a gourmet lunch paired with impeccable wine on an authentic Chianti farm.

Of course, no Tuscany day trip from Florence is complete without a visit to the wine region! Chianti is a postcard-perfect area full of rolling hills and quaint farmhouses. As the lunch hour draws near, you'll take a tour of a family-run farm and winery, complete with sprawling vineyards and full wine cellars.

Time for lunch—and trust us, it won't disappoint. The menu varies seasonally, as Tuscan cuisine is famously linked to produce and uses only the freshest ingredients for the heartiest, most delicious dishes. Paired with a selection of the vineyard's very own wines, this is Italian food at its finest—and it's all included in the price of your tour.

Explore the UNESCO World Heritage town of San Gimignano.

With full bellies, we'll move on to the picturesque town of San Gimignano—so visually stunning and architecturally significant that it’s a UNESCO World Heritage Site. You'll enjoy a full tour of the town, then have a bit of free time to shop for local Italian specialties or climb the city’s campanile for one of the best views in Tuscany.

From start to finish, the emphasis of our Tuscany day trip from Florence is on indulgence. Indulge in stunning scenery, delicious wines, and lazy strolls on our all-inclusive Tuscan adventure. We’ve taken care of all the details so all you have to worry about is how much Chianti wine you can fit in your suitcase.

Please note that this description is an example and your experience may vary depending on the season, day of the week, and group size. Regardless of where your tour goes, you always have an excellent experience.

Sites visited

Verified guest reviews, aug 13, 2024.

This was a very good tour of 3 cities including one winery. It was informative, fun, and well managed. There were some steep hills to walk up that one should know about before embarking on tour.

Aug 10, 2024

We had a fabulous time with our Tuscan tour! The entire day was seamlessly planned, with incredible sites, delicious food and most importantly an incredible guide. Pia was very knowledgeable and so enjoyable to be around! Thank you for a wonderful experience!!

Aug 02, 2024

Ismael was a wonderful tour guide. He was very professional and informative. The driver was extremely professional and courteous. The venues visited were excellent and this tour was a great value for the price charged.

Jul 21, 2024

Annette was a wonderful tour house, very knowledgeable and friendly. We had an amazing day, absolutely loved the winery lunch. Thank you Walks of Italy

May 28, 2024

Elana was great!! Locations were great,

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Similar tours, tastes & traditions of florence: food tour with sant'ambrogio market visit, the chianti experience: small group half-day wine tour from florence, pristine pisa: leaning tower, cathedral, city walls trip from florence.

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15 Best Day Trips from Florence

Are you looking for the best day trips from Florence Italy? Say nothing more, we’ve got you covered! You can find on our list of day trips out of Florence the best Tuscany day trips from Florence, but also the best day trips from Florence by train. We are also covering a Florence to Bologna day trip , as well as a day trip to Pisa and Lucca from Florence. Now, since Tuscany is a central region, we’ve included on the list some great day trips that you can plan out of the region too.

15 Best day trips from Florence Italy

Before diving into the best day trips from Florence, make sure you check the best luxury hotels, affordable hotels, and hostels in Florence ! We also cover restaurants in the city and other great things to do! The 15 best day trips from Florence Italy include as we’ve mentioned some of the best Tuscany day trips from Florence, and the best day trips from Florence by train. We’ve got some stunning Tuscan villages on our list as well as cities in the region and the neighboring regions too.

You can find some great ideas for the Emilia Romagna region, such as a Florence to Bologna day trip, but also day trips to Tuscany countryside from Florence. If you’re looking for good day trips from Florence we advise you not to think about a Florence to Venice day trip, since Venice is really far, and one day isn’t enough to see it. So if you’d like to visit Venice , definitely plan at least two or three days for it!

If you’re looking for day trips from Florence Italy , we must start with the second most beautiful town in Tuscany! Siena is one of the best day trips from Florence by train too, but you can reach Siena by car or bus as well. The town is located south of Florence, just about one and a half hours away from Florence.

When it comes to good day trips from Florence, and Tuscany day trips from Florence specifically, we, who have seen Siena can confirm, that this is definitely one of the best day trips in Tuscany you should do, and there are a million reasons why! Siena is the largest of the hill towns in Tuscany , a medieval town, that’s home to some amazing Gothic architecture, charming medieval streets, and amazing Tuscan food.

If you visit Siena , you must see the fabulous Piazza del Campo, the largest and one of the most significant medieval squares in Europe. Here you can also see the Palazzo Pubblico and the Tower of Mangia. Moreover, in Siena you can visit one of the most fascinating Renaissance cathedrals, the Duomo di Santa Maria Assunta, then try some truffles, wine , and other great local dishes! Make sure you check out the best hotels in Siena too!

One of the best Tuscany day trips from Florence is definitely Pisa! The Leaning Tower of Pisa is probably one of the most iconic landmarks not just in Italy, but the whole of Europe. If you’re looking for the best day trips from Florence by train, Pisa is always a winner, since you’ve got a direct line there.

The first thing to visit in Pisa is always the Piazza dei Miracoli, where you can find the Cattedrale Metropolitana Primaziale di Santa Maria Assunta (Cathedral of Pisa, or in Italian it’s also called Duomo di Pisa), with the stunning baptistery on the side, and the Leaning Tower of Pisa behind it. Though, if you want to visit Pisa, it’s always best to think about 2 destinations. A day trip to Pisa and Lucca from Florence could be a great pick for good day trips from Florence.

I’m saying to plan something else on the side because there’s not too much to see in Pisa outside the Piazza dei Miracoli. We wandered around everything significant in about 3 hours, then it’s always good to eat something local and delicious, but it’s not enough to fill the whole day. Therefore, if you plan a second destination that’s reachable from Pisa by train, or car, you can see two stunning places in Tuscany at once. However, Pisa is anyway one of the best day trips in Tuscany, so don’t miss it!

3. San Gimignano

There aren’t many places better for day trips from Florence Italy than the charming San Gimignano. Between the hills of Tuscany, and millions of vineyards, there’s this small hill town, with many medieval towers that you can see from far away. San Gimignano earned to be one of the best day trips out of Florence and to be one of the top day trips to Tuscany countryside from Florence, since its magical.

A perfect medieval town packed with the most amazing food, truffles, dishes made of cinghiale (boar) meat, porcini mushrooms, cheese , great wine , and sweets. Moreover, you can find dozens of local shops to buy famous Tuscan olive oil , more wine, and ceramics. The ceramics are stunning!

Can’t be missed in San Gimignano:

While you’re roaming the cute town of San Gimignano, make sure not to miss this pastry and chocolate bar called Armando e Marcella. The story of this place is so beautiful on its own, that it just can’t be missed. This bar is a family-owned business, Armando e Marcella are those who opened it, and you can still find Marcella (who I’d say is around 80 years old) making amazing cappuccinos and serving their clients so fast, that a bartender in their 20s’ wouldn’t do it like her!

A local man recommended this place to us, and I must say that I have never had such a great brioche with cream, and brioche with chocolate as what they make! They also sell sandwiches, all types of sweets, but homemade chocolate balls (THEY ARE INCREDIBLE!) as well as homemade chocolate cream, hazelnut cream (better than Nutella!), and homemade pistachio cream! I spent more money shopping in this one bar than during my whole Tuscany trip! The charming town, the towers, the food, and this bar all together make San Gimignano definitely one of the best day trips in Tuscany!

4. Volterra

Volterra is another of the best Tuscany day trips from Florence, and another of my personal favorite Tuscan hill towns. If you’re planning day trips to Tuscany countryside from Florence, visiting San Gimignano and Volterra together can be a perfect itinerary for good day trips from Florence. These two are fairly close to each other, however, you must travel either by car or bus. If you want to rent a car in Florence , check our article!

Volterra isn’t as famous as Siena or San Gimignano, but it is definitely a stunning destination with an incredible panorama over the Tuscan hills. The best in this town is that it actually has these medieval vibes with dragon symbols around the town. Volterra’s historic center and these medieval vibes are absolutely fascinating, and sometimes you might find yourself looking if a knight covered fully in armor will show up on the next corner.

The town is steeped in mystic folklore, and those who loved the Twilight saga, I’d remind you, that the Volturi vampires had their residence in Volterra, while the town is also visible in the New Moon movie . Possibly the town was picked for the Twilight saga due to the many vampire stories originating from Volterra.

While you’re exploring this stunning town, make sure to stop by at the Alabaster Museum, and plan a lunch or dinner in the town, to try some delicious local dishes! If you like porcini mushrooms, the Risotto con Funghi Porcini is definitely something you want to try in Volterra!

One of the most perfect day trips to Tuscany countryside from Florence is Chianti. The land of the perfect grapes, the land of vineyards, and the land of one of the most famous wines in the world, the Chianti wines. Chianti is one of the most unique winemaking regions in the world.

The squat wine bottled held in straw baskets that are called a fiasco, you can recognize a Chianti wine easily, and no sommelier will pass the opportunity to explore the wine region for sure! To visit this area, the best is always by car, since the vineyards are spread in the area. Otherwise, you can try local buses, a bicycle or a motorbike .

Also, since the wine region is worldwide famous, you can expect to find some of the highest quality restaurants from Italy, that are usually serving traditional Tuscan dishes, many times with a modern twist. Anyhow, any foodie will definitely leave Chianti with a happy stomach!

6. Montepulciano

Montepulciano is another of the best Tuscany day trips from Florence! A prime example of Tuscan beauty! The medieval hill town is home to Renaissance buildings, a labyrinth of cobbled streets, beautiful churches, great food, history, and wine.

If you want to think about some day trips out of Florence, and you’re looking for elegant, yet rustic, beautiful locations, day trips to Tuscany countryside from Florence, we say Montepulciano. To be honest, the best is always to get a car, and travel around 5-10 towns in Tuscany during a trip instead of doing 1-1 random day trips, however, in each case, Montepulciano is one to consider.

For wine lovers a Tuscany day trip from Florence to Montepulciano can be a perfect option, so you can visit vineyards, and try some of the most famous Italian wines that you’ve ever tasted. Since Montepulciano isn’t big either, if you’re in the area, you can combine a visit also to Cortona from here.

I previously mentioned that if you’re planning to visit Pisa, the best is always to do a day trip to Pisa and Lucca from Florence. Lucca is a perfect choice for some of the best day trips in Tuscany. The medieval town center that’s really unique since it has a perfect round form, thanks to the buildings surrounding it.

While you’re in Lucca, you must explore some of the most stunning architectures, such as the Guinigi Tower. You can see on the top the holm oak trees that stand proud on top of the tower, that’s absolutely incredible to see! Also, the above-mentioned round square, Piazza dell’Anfiteatro is packed with lovely cafes and restaurants serving local dishes and wine.

Here’s another great option for the best day trips from Florence by train, Perugia! Perugia’s pristine medieval city center and the international student population, this is a large cosmopolitan city in the region of Umbria . If you’re looking for good day trips from Florence, and you prefer cities over towns, but still at a distance that’s doable, definitely visit Perugia!

Once you’re there, you must try one of Italy’s most famous hazelnut-flavored chocolate, the Baci. One of the most delicious chocolate treats that I’ve tried so far! Also, you must visit the beautiful Gothic palaces around the city center as well as the Galleria Nazionale dell’Umbria, where you can see pieces displayed in more than 40 rooms!

In Perugia, you should be visiting Rocca Paolina, the Renaissance fortress, as well as Piazza IV Novembre, and stop by to try some traditional dishes from Umbria! From Florence, Perugia is about 2 hours drive, but if you’re planning a day trip from Florence by train, you could arrive within one and a half hours! If you need accommodation in the town, make sure you check our Perugia hotels list!

Since this list of day trips from Florence Italy are picked by me, and because I’m based in the Emilia Romagna region , I’ve got to visit them, I can’t ignore a Florence to Bologna day trip either. Bologna is the capital city of the Emilia Romagna region, and it’s definitely one of the most beautiful cities to visit in Italy!

The perfect foodie trip, where you can eat as much ragu, mortadella, tortellini, cheese, and whatever else you desire to eat, every corner is packed with bars serving all types of delicious local food, and restaurants serving the best dishes of Emilia Romagna. The city is considered the food capital of Italy, and besides eating, there’s a lot to do in the city too!

Since the University of Bologna is the oldest university in Europe, student life is on top levels. This makes Bologna a perfect destination for young adults especially and friend groups. Eat and party, then explore the Asinelli and Garisenda towers, walk under the millions of Porticos of the historic center, and visit the enormous Basilica di San Petronio.

Remaining still in the region of Emilia Romagna, beyond a Florence to Bologna day trip, you should definitely consider Modena as well! A medium-sized town that’s just about 30 minutes by train from Bologna Centrale and it’s a must-visit! The lively Emilian town is famous for many reasons, but first of all, like all the towns in Emilia Romagna, it’s famous for food!

Modena’s Aceto Balsamico (balsamic vinegar) is worldwide famous and it is definitely the best as well! Since you’re in the city, don’t miss some of the most famous restaurants in Modena, such as La Francescana or Trattoria da Ermes. Stroll on the Albinelli Market, stop for an Aperitivo and visit some local historic sights. Also, don’t forget that Modena is the home of Ferrari, and you can also visit the Enzo Ferrari museum, as well as you can sign up for a Ferrari driving experience too! Modena is also a great option for day trips from Bologna !

Yet another of the best Tuscany day trips from Florence to Arezzo. The hilltop town is easily reachable from Florence, and it is definitely a must-see since, beyond the medieval architecture and stunning panorama, there’s also a Roman amphitheater to visit. Moreover, there are plenty of churches and a fortress as well to explore in Arezzo!

The stunning historic center, the Piazza Grande, is just stunning. Moreover, the Medici Fortress on the top of the hill is unmissable, also for the spectacular panorama that it offers. Definitely, a lot of good food, wine, and local delicacies are to be found in Arezzo, so everyone can satisfy their curiosity and stomach too!

Another of the best Tuscany day trips from Florence is definitely Assisi. When you think of Assisi, I’m sure the first idea to spring to mind is that of Catholic pilgrimage, and whilst that is true there’s far more to this town than religion alone. Whether you are religious or not the following sights are well worth a visit to view their splendid architecture, absorb the history, and well feel a little spiritual too. Well, Assisi is one of the best small towns in Italy!

The Porziuncola at Santa Maria degli Angeli, the tomb of Saint Francis at the Basilica of Saint Francis, and the tomb of Saint Clare at the Basilica of Saint Clare. If you are in town during the Assumption of the Immaculate Conception, you can see Mary’s Veil in the Basilica. It is claimed that the veil was a gift to Mary from the Magi, this precious silk veil was used to swaddle baby Jesus.

While exploring the beautiful town, you can stop by for a Piadina ( flatbread sandwich) at Piadina Biologica, or dinner at Ristorante Vicoletto. Exploring this gem of Umbria is absolutely a must-do, and it is also easy to travel there if you’re looking for the best day trips from Florence by train!

13. Val d’Orcia

Val d’Orcia is by far the most beautiful countryside in Italy. The whole valley is a UNESCO Heritage Site, thanks to its incredible beauty! Val d’Orcia is best to be discovered by day trips from Florence Italy, or you can easily reach it from Siena (it’s much closer), but also from Rome .

The valley is famous for its amazing wine and cheese products, such as the famous Pecorino Romano cheese, but many others too. In Val d’Orcia, you can eat as much as you can, while talking with producers, and visiting factories, but also drive through the beautiful countryside that looks like a painting, and feel like you’d be driving in a painting.

14. Portovenere

Portovenere is by far one of those good day trips from Florence that bring you to the amazing and beautiful coasts of the Liguria region. After Cinque Terre and Portofino , Portovenere is another coastal town in Italy that’s absolutely beautiful and worth visiting! It’s also more affordable than Portofino!

Just south of La Spezia, Porto Venere also consists of more towns and islands . The three villages, are Fezzano, Le Grazie, and Porto Venere, and the three islands of Palmaria, Tino, and Tinetto. Porto Venere is also part of the UNESCO Heritage Sites, just like Cinque Terre . A really beautiful destination that you can add to your Italy itinerary if you’re looking for day trips from Florence by car.

15. Terme di Saturnia

Terme di Saturnia is becoming more and more popular thanks to the natural pools and cascades created by limestone made this place absolutely fabulous. When you ask me about the best day trips from Florence Italy, and especially about the best Tuscany day trip from Florence, Terme di Saturnia will be one that I really recommend.

It is indeed a natural beauty, that also creates a stunning atmosphere. Terme di Saturnia is one of the most famous thermal baths in Tuscany . However remember, that Terme di Saturnia is indeed one of the best day trips to Tuscany countryside from Florence, without a car, it’s difficult to get there. It’s also pretty far from Florence, but if you plan a Val d’Orcia and Terme di Saturnia trip together, it could absolutely be the best Tuscany day trip from Florence!

Now that we’ve covered the best Tuscany day trips from Florence, including tips for the best day trips from Florence by train, we hope that you’re ready for your next Italian adventure! All those who want to see more than just one city, and looking for day trips out of Florence could have found on this list all the possible good day trips from Florence that are actually doable in one day! The Tuscany day trip from Florence can include even more than one stop since in the small towns and villages there isn’t so much to do for a full day.

We also covered Emilia Romagna, Florence to Bologna day trips, but a day trip to Pisa and Lucca from Florence as well. Driving through the region was like magic, and I can say from the bottom of my heart, that there’s no place like Tuscany’s countryside. So by this, we hope you’ve found the best pick for you for day trips to Tuscany countryside from Florence. We did not include Florence to Venice day trip since Venice isn’t doable in one day and the travel time is significant too!

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