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Explore Montepulciano and Pienza from Siena on a Small-Group Day Trip in Tuscany
Discover the heart of Tuscany on a guided small-group day trip that takes you from Siena through the rolling clay hills to the UNESCO-protected landscapes of Val d’Orcia; you'll explore the charming towns of Pienza and Montepulciano, enjoy sweeping countryside views and savor lunch on a local farm, all with personalized attention thanks to the intimate maximum of eight guests on this tour.
About this activity in Siena
Cancellation policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
Highlights
- Discover Pienza and Montepulciano on a small-group day trip from Siena, wandering UNESCO-listed Val d’Orcia landscapes and hilltop streets.
- Enjoy panoramic views of the clay hills south of Siena as you travel between picturesque villages in the heart of Tuscany.
- Savor a farmhouse lunch paired with local wines - a chance to taste authentic regional cuisine and viniculture in this renowned area.
- Travel comfortably in a small group (maximum 8), so your guide can give you a more personal, focused experience of the region.
Important Information
- This experience explores iconic Tuscan scenery and historic towns - bring comfortable walking shoes for cobbled streets and short climbs.
- The tour is family-friendly: infants and small children can use a stroller, and specialized infant seats are available on request.
- Guests under Italy’s legal drinking age (18) will not be served alcohol during the farmhouse lunch.
- If you have cardiovascular concerns, this activity is not recommended; otherwise it suits a wide range of fitness levels.
Meeting Point
Meet in central Siena at Piazza del Campo near the Fonte Gaia; the exact pickup point and final meeting time will be confirmed on your booking confirmation.
Includes
- Ride in an air-conditioned minivan (maximum 8 passengers) for comfortable transfers around Siena, Tuscany
- Enjoy alcoholic beverages included during the experience in the region
- Savor a lunch on a local farm with wine, showcasing Tuscan flavors nearby
- Benefit from a knowledgeable driver/guide who accompanies you through the area
Excludes
- Hotel pickup and drop-off are not included - plan your arrival to the meeting point in Siena
- Gratuities for the driver/guide are not included
Other
- Infants and small children can ride in a pram or stroller when exploring the area
- Public transportation options are available nearby if you prefer alternative connections in the region
- Specialized infant seats are available for family comfort
- This activity is not recommended for travelers with poor cardiovascular health
- Suitable for all physical fitness levels, making it accessible to a wide range of visitors
- Customers who have not reached Italy's legal drinking age of 18 will not be served alcohol
Customer Reviews
10/10
Based on 10 Reviews
Summary:
Our guide Juilianna was fantastic! She was very knowledgeable about the area and the wine. A pleasure to be on this tour with her. I would recommend this day trip without reservation. It was great!
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Summary:
What a great day out with Keko as our enthusiastic and knowledgeable guide. The routes, coffee stop and both Penza and Montepulciano were all fantastic with plenty of free time to wander. The farm lunch was exceptional - not at all the mass tourist group place that such trips usually stop at.
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Summary:
Claudia was amazing. Terrific day; so informative and fun. She was personable and well versed in history and wine.
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Know more about Siena
On this guided small-group tour you’ll travel through the clay hills south of Siena and take in the UNESCO-protected Val d’Orcia landscapes, explore the charming hill towns of Pienza and Montepulciano, and enjoy panoramic views, historic streets, and local architecture unique to this part of Tuscany.
Group size is limited to a maximum of 8 persons to ensure personalized attention, and transport is provided by an air-conditioned minivan for comfortable travel between Siena, Pienza, Montepulciano, and the Val d’Orcia countryside.
The tour is suitable for all physical fitness levels, but it is not recommended for travelers with poor cardiovascular health due to walking and elevation in hill towns; plan accordingly and discuss any concerns with the operator when you book.
Yes - the itinerary includes lunch on a local farm with wine, giving you an authentic food-and-drink experience in the Val d’Orcia region that showcases regional cuisine and local wines from Montepulciano and surrounding vineyards.
The tour is family-friendly: infants and small children can ride in a pram or stroller and specialized infant seats are available, while the small group format makes it easier to accommodate families exploring the Tuscan countryside together.
The tour includes farm lunch with wine and driver/guide transport, but hotel pickup and drop-off and gratuities are excluded; additionally, customers under Italy’s legal drinking age of 18 will not be served alcohol, so plan travel logistics and tipping accordingly.
