Best Towns in Tuscany: 10 Gorgeous Villages You’ll Love to Visit

Would you like to explore stunning Tuscan towns, like Florence and Pienza? In this article you will find great tips on attractions, where to stay, and more!

Last updated: 31 July 202516 minute read

Planning a trip and wondering which are the best towns in Tuscany? This region has something for everyone: historic cities, charming villages plus great options for food and wine.

In this guide, you’ll discover 10 beautiful spots perfect for a base, a day trip or just to enjoy the Tuscan countryside.

1. Florence (Firenze): The Heart of Renaissance

​​Florence is the capital of Tuscany and one of the most famous cities in Italy. Known as the birthplace of the Renaissance, it’s the home of amazing landmarks like the Duomo with its big dome, the Ponte Vecchio bridge and the Uffizi Gallery with works by Botticelli and Leonardo da Vinci.

Walk through the old town, enjoy a stroll along the Arno River, stop for a gelato in Piazza della Signoria and finish the day with a bistecca alla fiorentina in a local trattoria. If you can, climb to Piazzale Michelangelo for an amazing sunset view of the city.

✅ Florence at a Glance

• Why go? Birthplace of the Renaissance, full of art, history and great food.
• Top sights: Duomo, Ponte Vecchio, Uffizi Gallery.
• Best view: Piazzale Michelangelo at sunset.
• Extra tip: Use Florence as your base for day trips to Siena, Pisa and Chianti.

🛏️ Where to Stay in Florence

• Art Hotel Villa Agape: Historical villa on a hill with garden and Florence views
• The Social Hub Florence Lavagnini: Rooftop terrace with pool and panoramic city views
• c-hotels Ambasciatori: Great location near the train station of Santa Maria Novella

2. Siena: Medieval Charm & Piazza del Campo

Siena is a smaller and a quieter city than Florence, perfect if you want a slower pace. It’s full of medieval charm and history. The heart of the city is Piazza del Campo, a beautiful square where the famous Palio horse race happens twice a year (on July 2 and August 16).

Don’t miss the Duomo, one of the most stunning Gothic cathedrals in Italy, with its detailed marble façade and rich interior. For amazing views of the city and of the Tuscan hills, climb the Torre del Mangia, the tall tower located in the main square.

Siena is also a great place to try local food like pici pasta and ricciarelli cookies. You can visit in one day, but staying overnight lets you enjoy its magical evenings.

✅ Siena at a Glance

• Why go? Medieval charm, Gothic architecture and the famous Palio horse race.
• Top sights: Piazza del Campo, Duomo di Siena, Torre del Mangia.
• Best view: From the top of Torre del Mangia.
• Extra tip: Visit in July or August to experience the Palio, but book early!

🛏️ Where to Stay in Siena

• Palazzo Ravizza: Historic charm, elegant interiors, great location in the city center
• Hotel Athena: Stunning panoramic views of the Tuscan countryside
• Hotel Alma Domus: Budget-friendly, Simple rooms, central location, breakfast included

3. San Gimignano: The Town of Towers

San Gimignano is one of the most unique towns in Tuscany, famous for its tall medieval towers that create a skyline like no other place in the world. This small hill town is a UNESCO World Heritage site and feels like stepping into the Middle Ages.

You can walk through its narrow streets in just a few hours. Stop at Piazza della Cisterna, look up at the towers and make sure to try the gelato at Gelateria Dondoli, often called the best in the world.

If you love wine, don’t miss a glass of Vernaccia di San Gimignano, the local white wine.

✅ San Gimignano at a Glance

• Why go? UNESCO-listed hill town with a unique skyline of medieval towers.
• Top sights: Piazza della Cisterna, Torre Grossa, Duomo di San Gimignano.
• Don’t miss: Gelato at Gelateria Dondoli and a glass of Vernaccia wine.

🛏️ Where to Stay in San Gimignano

• La Cisterna: Historic building with a prime location in Piazza della Cisterna
• Hotel Leon Bianco: Exceptional views and hot tub in the heart of the city
• Hotel Bel Soggiorno: Elegant setting with panoramic restaurant views

4. Pienza: The Ideal Renaissance Town

Pienza is one of the prettiest towns in the Val d’Orcia. It was redesigned in the 15th century as the “ideal Renaissance city” and today it’s famous for its perfect square, elegant buildings and amazing views over the Tuscan hills.

Start at Piazza Pio II, the main square, then walk through the quiet streets and stop in a shop to try Pecorino di Pienza, the local cheese.

If you can, stay until sunset. The view from the town walls over the Val d’Orcia is something you’ll never forget.

✅ Pienza at a Glance

• Why go? UNESCO World Heritage town with Renaissance architecture and amazing views.
• Top sights: Piazza Pio II, Pienza Cathedral, panoramic walls.
• Don’t miss: Tasting Pecorino di Pienza in local shops.

🛏️ Where to Stay in Pienza

• Hotel Relais Il Chiostro di Pienza: Historic building with pool and great breakfast
• Hotel Corsignano: Comfortable rooms, hot tub and stunning views
• PienzaLettings Suites: Modern suites with panoramic views

📌 If you want to explore more of Italy, check out our Top 10 Best Cities to Visit in Italy and When: discover the best time to go, what to see and why these cities are perfect for your trip.

5. Montepulciano: Wine Lover’s Paradise

Montepulciano is a hill town in southern Tuscany, best known for Vino Nobile di Montepulciano, one of the region’s most famous red wines. It has a mix of Renaissance buildings, cobblestone streets and great views of the countryside.

Start in Piazza Grande, the main square, then visit the wine cellars under the old palaces. Many offer free tastings, so you can try the local wine.

Take a walk through the streets, stop in small shops and check out the viewpoints for photos. If possible, stay until sunset for a nice view of the hills.

✅ Montepulciano at a Glance

• Why go? Home of Vino Nobile, Renaissance charm, amazing views.
• Top sights: Piazza Grande, Montepulciano Cathedral, historic wine cellars.
• Don’t miss: A wine tasting in one of the underground cantinas.

🛏️ Where to Stay in Montepulciano

• Etruria Resort & Natural Spa: Pool and great views of the Tuscan countryside
• Palazzo Nobile di San Donato: Elegant rooms in a historic building, breakfast included
• Bed & Breakfast Vicolo dell’Oste: Budget-friendly, Charming B&B in a central location

6. Montalcino: Home of Brunello Wine

Montalcino is a small town famous for Brunello di Montalcino, one of Italy’s best red wines. It’s a great stop for wine lovers and anyone exploring southern Tuscany.

Begin your visit at the 14th-century fortress, where you’ll find incredible views of the Val d’Orcia. Then, explore the quiet streets, stop in a local enoteca and try some Tuscan specialties.

If you have time, don’t miss the Abbazia di Sant’Antimo, a beautiful Romanesque abbey just a short drive from the town. Surrounded by olive trees and vineyards, it’s one of the most peaceful spots in Tuscany.

✅ Montalcino at a Glance

• Why go? Birthplace of Brunello, medieval charm, amazing wine culture.
• Top sights: Rocca di Montalcino, Sant’Antimo Abbey, scenic vineyards.
• Don’t miss: A Brunello tasting with a view of the hills.

🛏️ Where to Stay in Montalcino

• Mastrojanni Relais: Elegant wine resort with pool and amazing countryside views
• Hotel Dei Capitani: Great location with panoramic terrace and outdoor pool
• Idolina Guest House: Cozy guesthouse with breakfast included and friendly service

7. Volterra: Etruscan History & Alabaster Art

Volterra is one of the oldest towns in Tuscany, with history that goes back to the Etruscans. It’s a great choice if you want a quiet, authentic experience away from the big crowds.

Visit the Etruscan Museum to see ancient artifacts, then explore the medieval streets filled with small shops and artisans carving alabaster, a local tradition. You can even buy a handmade piece as a souvenir.

Then head to Palazzo dei Priori, the oldest town hall in Tuscany, located in the main square. After that, don’t miss the Roman Theatre, one of the best-preserved in Italy and a great spot for photos.

✅ Volterra at a Glance

• Why go? Rich Etruscan history, authentic atmosphere, local crafts.
• Top sights: Etruscan Museum, Palazzo dei Priori, Roman Theatre.
• Don’t miss: Watching alabaster artisans at work.

🛏️ Where to Stay in Volterra

• Albergo Villa Rioddi: Historic villa with pool and countryside views
• Hotel Volterra In Superior: Stylish and elegant, perfect for a central stay
• Albergo Etruria: Great location in the historic center, cozy rooms

8. Cortona: Under the Tuscan Sun Vibes

Cortona is a lovely hilltop town that became famous thanks to the book and movie Under the Tuscan Sun. It’s full of charm, with small streets, pretty squares and amazing views of the Val di Chiana.

Begin your visit with a stroll through the narrow streets, stopping in Piazza della Repubblica, the heart of Cortona. Check out the MAEC Museum for a mix of Etruscan and Renaissance treasures.

After that, take your time to wander: there are plenty of viewpoints with amazing views of the valley. Sunset is a great moment to enjoy them.

✅ Cortona at a Glance

• Why go? Romantic hilltop town with breathtaking views and cultural treasures.
• Top sights: Piazza della Repubblica, MAEC Museum, panoramic viewpoints.
• Don’t miss: Enjoying a glass of wine at sunset overlooking the valley.

🛏️ Where to Stay in Cortona

• Villa di Piazzano: 16th-century villa with pool and stunning countryside views
• Monastero di Cortona Hotel & Spa: Historic monastery with spa and panoramic terrace
• Hotel San Michele: Central location, charming and cozy atmosphere

9. Lucca: Renaissance Walls & Slow Living

Lucca is a Tuscan town known for its Renaissance walls that surround the historic center. Rent a bike and ride on top of the walls for a great view of the city.

Inside, visit Piazza dell’Anfiteatro, the Lucca Cathedral and San Michele in Foro. Don’t miss the Guinigi Tower, with its small garden at the top. After sightseeing, relax in a café or grab a gelato.

If you’re visiting in late October or early November, you might catch Lucca Comics & Games, one of Europe’s biggest comic and gaming festivals.

✅ Lucca at a Glance

• Why go? Renaissance walls, peaceful streets, and authentic Tuscan charm.
• Top sights: Piazza dell’Anfiteatro, Lucca Cathedral, Guinigi Tower.
• Don’t miss: Cycling on the historic city walls.

🛏️ Where to Stay in Lucca

• Hotel Ilaria: Great location near the city walls
• Albergo San Martino: Cozy and welcoming, close to main attractions
• San Luca Palace Hotel: Elegant rooms, central location and breakfast included

10. Arezzo: Art, Antiques & Authentic Tuscany

Arezzo is a town in eastern Tuscany that many travelers skip, so it’s a great choice if you want a quieter and more authentic experience.

It’s full of medieval charm and art. Begin your visit at Piazza Grande, one of the most beautiful squares in Italy. Then visit the Basilica of San Francesco to see Piero della Francesca’s famous frescoes.

If you visit on the first weekend of the month, you’ll find Arezzo’s famous antique fair. It’s one of the biggest in Italy, with hundreds of stalls selling furniture, art, jewelry and vintage items.

✅ Arezzo at a Glance

• Why go? Rich in medieval art, quiet atmosphere, local traditions.
• Top sights: Piazza Grande, Basilica of San Francesco, antique market.
• Don’t miss: Piero della Francesca’s frescoes and local trattorias.

🛏️ Where to Stay in Arezzo

• Cameracaffè Centro: Great breakfast, lovely terrace and central position
• Hotel Continentale: Rooftop terrace with city views, central location
• Antiche Mura: Historic charm and cozy atmosphere

Bonus! Pisa: More Than Just the Leaning Tower

Pisa is world-famous for its Leaning Tower, but there’s more to see than this iconic landmark. The tower is part of Piazza dei Miracoli (Square of Miracles), a UNESCO World Heritage site that also includes the Cathedral and the Baptistery, both worth a visit.

Take a walk along the Arno River and explore the city’s historic streets. Pisa has a lively atmosphere, thanks to its large student population and plenty of cafés and trattorias where you can enjoy classic Tuscan dishes.

✅ Pisa at a Glance

• Why go? To see the Leaning Tower and explore a vibrant university city.
• Top sights: Leaning Tower, Piazza dei Miracoli, Baptistery.
• Don’t miss: A photo with the tower and a walk along the Arno River.

🛏️ Where to Stay in Pisa

• Grand Hotel Duomo: Just steps from the Leaning Tower, rooftop terrace with views
• Hotel Bologna: Central location with cozy and stylish rooms
• Prato dei Miracoli Residenza d'Epoca: Stunning view of the Leaning Tower, elegant historic charm

Bonus! How to Get Around Tuscany

The best way to explore Tuscany is by car. Having your own vehicle gives you the freedom to visit small hill towns, stop for photos in the countryside and travel at your own pace. Most villages are not well-connected by public transport and parking is usually available just outside the historic centers.

If you don’t want to drive, you can still get around by train and bus, especially between major cities like Florence, Siena, Pisa and Lucca. Trains are frequent and comfortable, while buses often cover the routes that trains don’t reach.

✅ Quick Travel Tips

• By Car: Ideal for exploring rural areas like Val d’Orcia or Chianti. Rent the vehicle from Florence or Pisa for the best options.
• By Train:
  • Florence → Siena: ~1h 30m by bus (faster than train)
  • Florence → Pisa: ~1h by train
  • Pisa → Lucca: ~30 min by train
• By Bus: Great for reaching smaller towns, but check schedules in advance.

Bonus! Best Time to Visit Tuscany

Tuscany is beautiful all year round, but the best time to visit is during spring (April-June) and autumn (September-October). The weather is mild and there are fewer crowds compared to the summer months. These seasons are perfect for sightseeing, wine tasting and enjoying outdoor activities without the heat.

Summer (July-August) is high season, so expect more tourists and higher prices, especially in popular towns like Florence and Siena. It can also get very hot, with temperatures often above 30°C (86°F).

Winter (November-March) is the quietest period. Some small towns may feel very calm, but it’s a great time to explore cities, enjoy museums without crowds and find better hotel deals.

Conclusion

Tuscany is easy to enjoy if you plan well. Choose a few key towns instead of trying to see everything in one trip. Renting a car is the best option to explore the countryside and smaller villages, while trains work well for major cities.

Take advantage of local experiences: wine tastings, small trattorias and scenic walks. Finally, book your accommodation early if you’re traveling in summer or during popular events like the Palio in Siena.

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