Montepulciano, Pienza, and the Essence of Val d'Orcia

About this experience

Embark on an exclusive Val d’Orcia tour, starting from Florence or any Tuscan location, for an unforgettable journey through rolling hills, medieval towns, and world-renowned flavors. Guided by expert local drivers, you'll explore Montepulciano, where history and wine intertwine, tasting the prestigious Vino Nobile in ancient cellars. Admire the breathtaking views of the Vitaleta Chapel, soak in the postcard-perfect landscapes of Val d’Orcia, and stroll through Pienza, a UNESCO-listed Renaissance gem known for its delicious Pecorino cheese. Delight in the thermal charm of Bagno Vignoni and uncover hidden corners of Tuscany that few travelers experience. Each stop is carefully selected to immerse you in the region’s rich heritage, flavors, and traditions. With a flexible 10-hour itinerary, tailored to your preferences, this tour ensures a perfect balance of discovery, relaxation, and authentic Tuscan charm.

Itinerary

English information from the provider

1. Stop 1

   Before arriving in the Valdorcia region you will travel through Tuscany and the enchanting province of Siena passing through some small towns

2. Stop 2

   Duration: 45 min

   We will arrive in the center of Montepulciano, rich in medieval and Renaissance history. Montepulciano is the center of a rich wine producing area. The most important product is the Vino Nobile di Montepulciano appreciated all over the world. We will arrive in the center of Montepulciano, rich in medieval and Renaissance history. Montepulciano is the center of a rich wine producing area. The most important product is the Vino Nobile di Montepulciano appreciated all over the world. In the Piazza Grande there are some beautiful 16th century Palaces, the Cathedral and the iconic medieval Palazzo Pubblico seat of the Municipal Government.

3. Stop 3

   Duration: 90 min

   The Cantina De' Ricci is one of the most impressive and unexpected attractions of Montepulciano. Through travertine stairs you will descend into the caves dug into the tuff that through the millennia have been used to preserve food and the precious Vino Nobile. At the end of the visit a Lunch will be served with typical dishes accompanied by tastings of local wines

4. Stop 4

   Duration: 30 min

   After lunch you will have free time to explore the Medieval city on foot and going down to the city gate you will find yourself walking through the alleys. You cannot miss an Italian espresso at the ancient Poliziano café with its Art Deco furnishings

5. Stop 5

   Duration: 15 min

   On the road from Montepulciano to Pienza you can stop to visit one of the most awarded Pecorino cheese producers in the world. The Cugusi dairy is renowned throughout the world. On its property if you are lucky you will meet the sheep at pasture you will enjoy a breathtaking view of the city of Montepulciano or seen from the countryside and you can obviously taste the Certified Pecorino di Pienza.

6. Stop 6

   Duration: 60 min

   Nestled in the rolling hills of Tuscany, Pienza is a charming Renaissance gem and a UNESCO World Heritage Site. Designed by Pope Pius II as the "ideal city," its elegant streets, breathtaking panoramic views, and delightful artisan shops make it a must-visit destination. Stroll through Piazza Pio II, admire the stunning cathedral, and indulge in the town’s famous Pecorino cheese. A true postcard-perfect experience in the heart of the Val d’Orcia!

7. Stop 7

   Duration: 10 min

   Set amidst the golden fields and cypress-lined hills of the Val d’Orcia, the Cappella di Vitaleta is one of Tuscany’s most photographed landmarks. This charming, solitary chapel exudes a mystical beauty, standing gracefully against the breathtaking landscape. A symbol of serenity and harmony, it offers visitors a moment of peace and an unforgettable view of the rolling Tuscan countryside. A picture-perfect stop on your journey through this UNESCO-listed paradise!

8. Stop 8

   Duration: 30 min

   Perched on a hilltop in the heart of the Val d’Orcia, Monticchiello is a charming medieval village where time seems to stand still. Enclosed by ancient stone walls and winding streets, it offers breathtaking views of the surrounding Tuscan countryside. Known for its rich history, picturesque beauty, and the famous Teatro Povero, Monticchiello is an enchanting stop for those seeking authenticity and timeless charm. This stop also comes at the perfect moment to enjoy a delicious Italian gelato, making your visit even sweeter as you soak in the magical atmosphere of this hidden gem!

9. Stop 9

   Duration: 30 min

   Located in the stunning Val d’Orcia, Bagno Vignoni is a unique village famous for its ancient thermal waters. Instead of a traditional piazza, the heart of the town is a large, steaming thermal pool, once used by the Romans and even frequented by Lorenzo de’ Medici. Walking through its charming streets, you’ll find breathtaking views, soothing hot springs, and a peaceful, timeless atmosphere.

What's included

English information from the provider

• Private transportation
• Air-conditioned vehicle
• Light Lunch in a historic cellar in Montepulciano that includes wine tasting of at least 4 different wines. On request we can agree on vegetarian, vegan, gluten free and minors menus

What's not included

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• Gratuities

Additional information

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• Infants and small children can ride in a pram or stroller
• Service animals allowed
• Specialized infant seats are available
• Suitable for all physical fitness levels

Cancellation policy

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