Best Day Trips from Siena, Italy

Explore the beautiful Tuscan countryside and nearby cities with these top day trips from Siena!

1. San Gimignano (30 miles/48 km)

Known as the “Town of Fine Towers,” this medieval hill town boasts a skyline filled with towers from the wealthy families who built them in the Middle Ages. Stroll through its historic center, visit the Collegiate Church of Santa Maria Assunta, and taste local white wine Vernaccia di San Gimignano.

2. Monteriggioni (19 miles/30 km)

A picturesque medieval walled town, Monteriggioni is a perfect stop on your way to or from San Gimignano. Its well-preserved walls and towers have remained unchanged for centuries, offering an authentic glimpse into Tuscany’s past. Be sure to check out the Church of Santa Maria Assunta inside the walls.

3. Chianti Wine Region (25 miles/40 km)

Rolling hills covered in vineyards, charming villages, and delicious wine – the Chianti region is a must-visit when in Siena! Rent a car or join a guided tour to explore this picturesque area and sample some of the world-famous Chianti Classico wines.

4. Pisa (70 miles/113 km)

Famous for its leaning tower, Pisa offers more than just an iconic photo opportunity. Visit the Piazza dei Miracoli (Square of Miracles), explore the Cathedral and Baptistery, and stroll along the Arno River. If you’re a university student, be sure to check out the Scuola Normale Superiore di Pisa – one of Italy’s most prestigious academic institutions.

5. Volterra (40 miles/64 km)

A charming Etruscan hill town, Volterra offers a unique glimpse into ancient civilization. Explore its historic center, visit the Guarnacci Etruscan Museum, and wander through the Alabaster workshops that have been producing this local craft for centuries.

6. Montalcino (53 miles/85 km)

Home to one of Italy’s most famous wines – Brunello di Montalcino – this hill town offers stunning views, medieval architecture, and delicious food. Climb the Fortress of Montalcino for panoramic vistas, visit the Abbey of Sant’Antimo, and sample some local wine in a local enoteca (wine shop).

7. Orvieto (62 miles/100 km)

Perched atop a volcanic plug, Orvieto boasts stunning views over the Umbrian countryside. Its historic center is filled with medieval and Renaissance architecture, including the massive Orvieto Cathedral and the Pozzo di San Patrizio (St. Patrick’s Well). Be sure to try some local black truffles and Underground Orvieto wine!

Tips:

• Rent a car for the most flexibility, but be aware of driving in Italy.
• Check opening hours for attractions, as they may change due to season or COVID-19 restrictions.
• Wear comfortable shoes and bring water for long walks.
• Taste local cuisine at each destination, such as pasta e fagioli (bean soup), pici (thick homemade spaghetti), crostini di fegato (liver bruschetta) and schiacciata all’uva (grape focaccia).
• Enjoy your day trips and discover the beauty of Tuscany!