15/Oct/2024

Top 10 Towns To Visit in Tuscany

Art Romance Daytrip Countryside Tuscany

Whether you are interested in history, food, scenery or looking to spend a day on the beach, here is our selection of the best 10 towns in Tuscany that you should add to your itinerary

Tuscany boasts an enchanting countryside, medieval architecture, and timeless beauty; it’s no wonder this region has long been a popular destination among tourists. And yet, in spite of this, many people refrain from venturing beyond larger cities like Florence. For those ready to deep dive into the region’s hidden gems, here’s a guide of ten must-visit towns in Tuscany; each brimming with charm and history. So whether you’re drawn to ancient heritage, culinary treasures, or scenic views, these towns promise an unforgettable journey into the heart of this stunning region.

 
 

10. Volterra

Famous For: Etruscan heritage and alabaster craftsmanship.
 
Volterra promises a journey through the area’s complex layers of history. From its Etruscan roots to Roman and medieval architecture, there’s no shortage of antiquity in this small Tuscan town. Given this, history lovers will not want to miss a visit to its Etruscan Museum and Roman Theater. And those looking to bring home a piece of Volterra’s heritage, be sure to pick up on handcrafted alabaster artwork; an artisanal tradition dating back to Etruscan era!
 
 

9. Arezzo

Famous For: Antique fairs and Piero della Francesca’s frescoes.
 
A vibrant town, Arezzo strikes the perfect balance between artistic heritage and a thriving local culture. Drawing in collectors from far and wide, the town hosts a monthly antique market in its trapezoid-shaped Piazza Grande. This alone makes it a popular spot for shoppers! But Arezzo is also home to the famed fresco cycle by artist Piero della Francesca. Located in the Basilica di San Francesco, this is a must-visit on any art lover’s itinerary.
 
 

8. Montalcino

Famous For: Brunello di Montalcino wine and rolling vineyards.
 
Another popular hilltop town, Montalcino is renowned across the world for its production of Brunello wine. Vineyards surround this picturesque, medieval town, making it a popular destination for both wine lovers and anyone enchanted by the iconic Tuscan landscape. From wine tastings at local wineries to taking in the history at the Fortress of Montalcino, Montalcino has something for everyone.
 

7. Castiglione della Pescaia

Famous For: Seaside charm and picturesque old town.

 

Located in Tuscany’s rugged Maremma area, this coastal gem combines medieval history with beachside ambience. Its historic center features narrow lanes and the Aragonese Castle, which offers beautiful views of the Tyrrhenian Sea. Known for its beautiful beaches and fresh seafood, Castiglione della Pescaia is an ideal choice for those seeking to enjoy both historic charm and coastal relaxation.

 

 

6. Montepulciano

Famous For: Renowned Vino Nobile wine and captivating Renaissance architecture.

 

Set in Tuscany’s scenic countryside, Montepulciano is a household name across the world, thanks to the production of its famous red wine. It offers a delightful blend of beautiful architecture and exquisite wine culture. At the heart of this Renaissance town is Piazza Grande, home to quaint cafes and an imposing clock tower. Meanwhile, to the delight of wine enthusiasts, beneath the streets of Montepulciano are a plethora of wine cellars that offer tastings of the town’s famed Vino Nobile red wine.

 

  

5. Monteriggioni

Famous For: Enchanting medieval fortress and preserved town walls.

 

A hilltop town, Monteriggioni offers panoramic views of the Chianti countryside and Siena, with its well-preserved fortress. Visitors can walk along its ancient walls to immerse themselves in the town’s medieval history. Boasting fourteen towers, the walls of Monteriggioni completely encircle the town. Meanwhile, located in the town’s main square is the Church of Santa Maria Assunta; an example of simple and rustic architecture. Finally, visitors can make a stop at the "Monteriggioni in Arme" museum for a snapshot of medieval and Renaissance weapons and

 

 

4. Pitigliano

Famous For: Dramatic cliffside setting and historic Jewish community.

 

Sitting on a striking cliff, Pitigliano boasts a rich cultural history. It offers a unique blend of natural beauty and history, making it one of Tuscany's most unique towns. With its historic synagogue and an ancient Jewish quarter, this town is also often nicknamed "Little Jerusalem". For a thrilling experience, visitors should consider a walk through the Vie Cave, the hollow cave-like Etruscan roads that connect to the nearby town of Sovana.

 

 

3. San Gimignano

Famous For: Medieval towers and UNESCO World Heritage status.

 

To soak in views of the stunning Tuscan countryside, climb Torre Grossa, which also happens to be San Gimignano’s tallest tower. This picturesque town is also known as the "Medieval Manhattan", thanks to its impressive skyline of towers. While here, wander through Piazza della Cisterna, the town’s charming and quirky triangular-shaped square. To learn more about the town’s storied past, visitors can opt to explore the Civic Museum, which dates back to the 13th century.

 

 

2. Cortona

Famous For: Etruscan roots and panoramic valley views.

 

Perched on a hilltop, the medieval town of Cortona offers stunning views of the Val di Chiana and Lake Trasimeno. Boasting a blend of ancient history and sweeping vistas, it’s a must-see for archaeology buffs and landscape lovers. A visit to the MAEC Museum can offer insight into its history, thanks to an impressive display of Etruscan artifacts. Meanwhile, for a blend of history and incredible panoramas, consider taking a stroll up to the Fortress of Girifalco. Built in the 16th century over an existing Etruscan fortress, it stands at over 600 meters above sea level, making it the highest point of the town. Cortona has also risen to fame thanks to the movie (and book) Under the Tuscan Sun.

 

 

1. Pienza

Famous For: Pecorino cheese and Renaissance architecture.

 

Regarded by many as the "ideal Renaissance town," Pienza is also synonymous with Pecorino cheese. This charming town boasts streets lined with shops selling the locally-produced sheep’s milk cheese. It offers the perfect blend of architectural beauty and culinary delights, making it a paradise for food lovers and history buffs alike. Visitors will want to make a stop at Palazzo Piccolomini, which offers elegant gardens and breathtaking views of the Val d’Orcia.