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Montepulciano and Pienza Small-Group Day Trip from Siena with Lunch
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Montepulciano and Pienza Small-Group Day Trip from Siena with Lunch

by Tuscan Escapes

8 hours
Siena
€171€190 on ViatorSave 10%/person
From
€171€190 on ViatorSave 10%per person

Choose from 1 available option

8 hours
Starting time
Friday 11 September 2026
Language
English
Free cancellation until 10 Sept 2026.
€342€380Save 10%
2 adults × €171
All taxes and fees included

How do you want to book?

Confirmation before Wed, 9 Sept - card's only charged if it's a yes. If it's a no, still time to book on Viator.

Book on Viator Confirmed right away, but you pay full price.€380

Overview

The tour begins at 9:30 AM in front of the church of San Domenico in Siena, where travelers meet the guide. The group travels south by air-conditioned minivan along the panoramic Crete Senesi road, passing through clay hills and moon-like landscapes. There are short photo stops at scenic points and a visit to a small medieval hamlet. Next, the tour reaches the Renaissance town of Pienza in the Val d’Orcia UNESCO World Heritage area. Visitors spend about an hour exploring Pienza’s historic center, including the planned layout commissioned by Pope Pius II. A 15-minute visit to Il Duomo di Pienza allows time to see the Romanesque cathedral and walk along scenic routes overlooking the surrounding hills and valleys. Guests may browse local craft shops during free time. Lunch takes place at a Val d’Orcia dairy farm where the group learns about pecorino sheep cheese production and farm life. Weather permitting, the meal is served on a terrace with views over the valley. In the afternoon, the group visits Montepulciano, a large Tuscan hill town with architecture reflecting its history under Siena and Florence. Visitors walk through Montepulciano’s streets and spend about an hour exploring. The final stop is Piazza Grande in Montepulciano, where guests tour one of the historic wineries carved into the hillside and taste Vino Nobile wine. After a guided walk around the square, there is free time for a second wine tasting or to visit shops, palaces, and churches. The tour lasts about 8 hours and includes transport, lunch, alcoholic beverages, and a driver-guide. Pickup and drop-off at hotels are not included. The group size is limited to 8 people.

Highlights

Small-group minivan tour with maximum 8 passengers
Visit Renaissance town of Pienza and Il Duomo di Pienza
Lunch at a Val d’Orcia dairy farm with cheese tasting
Explore Montepulciano hill town and Piazza Grande
Wine tasting of Vino Nobile in historic Montepulciano winery
Travel through Crete Senesi and Val d’Orcia landscapes

What's included

Transportation by air-conditioned minivan with up to 8 passengers
Alcoholic beverages served during the tour
Lunch at a local dairy farm
Services of a driver and guide

What's not included

Hotel pickup and drop-off services
Gratuities for guide and driver

Itinerary

1

Basilica Cateriniana Di S. Domenico

Meet the guide at 9:30 AM in front of San Domenico church in Siena, which is easy to find and has nearby parking. Then travel south on a scenic route through the clay hills and moonscapes of the Crete Senesi region.

2

Crete Senesi Photo Stops and Medieval Hamlet

Make brief stops along the Crete Senesi for photographs. Visit a small, non-touristic medieval village before continuing through the landscape to the UNESCO Val d’Orcia area, known for its iconic views.

30 min

3

Historic Centre of the City of Pienza

Arrive at Pienza, a Renaissance town designed on paper by architects hired by Pope Pius II to renovate his hometown. Spend about one hour exploring the historic center and its layout.

60 min

4

Il Duomo di Pienza

Spend 15 minutes visiting the Romanesque church called Corsignano or the Renaissance Cathedral. Walk along scenic paths overlooking valleys and browse local shops selling crafts and products.

15 min

5

Val D'Orcia

Enjoy an hour at a dairy farm in Val d’Orcia where lunch is served mainly with fresh farm ingredients. Learn about pecorino cheese production, visit the animals, and if weather allows, eat on a terrace overlooking the valley.

60 min

6

Montepulciano

Visit Montepulciano, a large hill town historically influenced by Siena and Florence. Spend an hour exploring its architecture and views over the Tuscany-Umbrian border.

60 min

7

Piazza Grande a Montepulciano

Spend 30 minutes at Montepulciano’s main square. Tour a historic winery carved into the rock and taste Vino Nobile wine produced by noble families. After a guided walk, enjoy free time for a second wine tasting or to visit shops, palaces, churches, and streets. The itinerary may vary slightly but retains the same duration and inclusions.

30 min

Meeting point

Meet your guide in front of the church of San Domenico in Siena at 9:30am, easy to find even if you are arriving from out of town with your own car, as there is parking in the vicinity.

End point

Meet your guide in front of the church of San Domenico in Siena at 9:30am, easy to find even if you are arriving from out of town with your own car, as there is parking in the vicinity.

Languages

English (guide)

Cancellation policy

  • Cancel at least 24 hours before start for a full refund.

Additional info

1–9 travelers per booking
Mobile ticket
Pushchair and stroller friendly
Reachable by public transport
Infant seats are available
Not advised for anyone with a heart condition
Suitable for all fitness levels
Alcoholic drinks are not served to customers under Italy’s legal drinking age of 18
Total
€342Save 10% vs Viator