Val d’Orcia Day Trip from Florence with Wine and Cheese Tasting

Escape Florence for a full-day journey through the heart of Tuscany’s Val d’Orcia, a UNESCO World Heritage landscape of rolling hills, vineyards, olive groves, and cypress-lined country roads. Visit three of the region’s most beautiful towns, Montalcino, Pienza, and Montepulciano, each known for its history, views, and authentic Tuscan character. Begin in Montalcino, home of the world-famous Brunello wine, where you’ll visit a wine cellar and enjoy a tasting. Continue to Pienza, the Renaissance “ideal city,” famous for its architecture, panoramic views, and Pecorino cheese. Finally, explore Montepulciano, renowned for Vino Nobile, and enjoy another wine and Pecorino tasting inside a historic underground cellar before returning to Florence.

1. 1

   Stop 1

   1.5 hours

   Meet your tour leader at the Tours & News Kiosk at Piazzale Montelungo Bus Terminal, located about 5–10 minutes on foot from Santa Maria Novella Train Station. Look for staff wearing a fuchsia jacket before departing Florence.

2. 2

   Val D'Orcia

   Pass by

   Travel through the scenic Val d’Orcia, a UNESCO World Heritage landscape famous for rolling hills, vineyards, olive groves, cypress trees, and postcard-perfect countryside views. Enjoy the beauty of classic Tuscany as you move between Montalcino, Pienza, and Montepulciano.

3. 3

   Montalcino

   1.5 hours

   Visit Montalcino, a charming Tuscan hilltop town known worldwide for Brunello wine. Enjoy time to wander through its picturesque streets and admire panoramic views over the countryside, vineyards, olive groves, and cypress-lined roads.

4. 4

   Montalcino

   1.5 hours

   Visit a wine cellar in Montalcino and discover one of Tuscany’s most celebrated wine traditions. Enjoy a tasting of Brunello wine and learn more about the flavors that make this area famous.

5. 5

   Pienza

   1.5 hours

   Explore Pienza, the Renaissance “ideal city” designed in the 15th century for Pope Pius II. Admire architectural landmarks such as the Duomo and Palazzo Piccolomini, enjoy panoramic views over Val d’Orcia, and taste the famous Pecorino cheese of Pienza.

6. 6

   Montepulciano

   1.5 hours

   Continue to Montepulciano, a beautiful hilltop town famed for its Vino Nobile vineyards, Renaissance architecture, and cinematic charm. Enjoy free time to explore its historic streets and soak in the atmosphere of one of Tuscany’s most elegant wine towns.

7. 7

   Montepulciano

   1.5 hours

   End the Tuscan tasting experience inside a historic underground cellar in Montepulciano. Savor Vino Nobile wine and Pecorino cheese while surrounded by the atmosphere of one of Tuscany’s most traditional wine towns.

8. 8

   Val D'Orcia

   30 min

   If included in the final route, enjoy the opportunity to retrace or view the famous Gladiator’s Walk, one of the most iconic countryside scenes associated with the Val d’Orcia landscape. This is a great stop for photos and panoramic views.

9. 9

   Florence

   1.5 hours

   Relax on the return journey to Florence after a full day of Tuscan towns, wine cellars, Pecorino cheese, and Val d’Orcia landscapes.

• Public transportation options are available nearby
• Specialized infant seats are available
• Suitable for all physical fitness levels
• Comfortable walking shoes are recommended

For a full refund, cancel at least 24 hours before the scheduled departure time.