Small-Group Montepulciano and Pienza Day Trip from Siena
Overview
Available languages
8 hours
Mobile ticket
Experience the heart of Tuscany on this guided small-group tour day trip to the charming towns of Pienza and Montepulciano. Travel through the beautiful clay hills south of Siena and take in the idyllic UNESCO protected landscapes of Tuscany's charming Val d’Orcia region. Explore the beautiful towns, enjoy the landscapes and have lunch on a local farm!
Numbers are limited to a maximum of 8 persons on this small-group tour, ensuring you'll receive personalized attention from your guide.
Additional Info
Infants and small children can ride in a pram or stroller
Public transportation options are available nearby
Specialized infant seats are available
Not recommended for travelers with poor cardiovascular health
Suitable for all physical fitness levels
Customers who have not reached Italy's legal drinking age of 18 will not be served alcohol
What To Expect
Basilica Cateriniana Di S. Domenico
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. Travel south out of town on one of the most panoramic roads of Tuscany, through the characteristic moonscapes of the Crete Senesi.
Enjoy brief stops along the Crete Senesi for for photo opportunities before visiting a quaint, non touristic medieval hamlet. Continue along this stunning landscape and reach the UNESCO heritage site of the Val d’Orcia, where you come across some of Tuscany’s most iconic postcard pictures.
Options
Small-Group Montepulciano and Pienza Day Trip from Siena
What‘s Included
Transport by air-conditioned minivan (maximum 8 passengers)
Alcoholic Beverages
Lunch on local farm with wine
Driver/Guide
Hotel pickup and drop-off
Gratuities
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
Reviews
316 reviews
Total reviews and rating from Viator & Tripadvisor
Fabulous day, great guide!
toddg2225301,Jun 23, 2026
- Review from Tripadvisor
5.00A fabulous day of touring, education, food, and wine. Our guide, Keko, was superb. The beautiful drive through the Val d'Orcia was made all the more memorable by the extensive history and cultural insights provided by Keko. We learned A LOT. Pienza was a pleasant stroll, but the highlight was Montepulciano if just for the views of Tuscany. Definitely a day well spent, made all the more memorable by having a fantastic guide. Well done, Keko!
The Perfect Tour
Renata I,Jun 16, 2026
- Review from Tripadvisor
5.00It was a perfect day with our guide Giorgia. The chosen places were very beautiful, as was the food and the wines. Giorgia was very kind and also helped each member of the group who had different needs or desires. She told the history of Siena, Chiusure, Pienza, Montepulciano, and other villages in a very pleasant way, and it is clear that she knows everything very well.
Unforgettable experience with Juliana!
703sheam,Jun 15, 2026
- Review from Tripadvisor
5.00I recently took the Pienza and Montepulciano Tour from Siena with Tuscan Escapes, and our guide, Juliana, made the entire day unforgettable. She was incredibly knowledgeable, warm, and passionate about the region, bringing the history and culture of both towns to life. Her local recommendations were absolutely spot on..Tip for future travelers: Be sure to bring cash with you for a tip! They do not have an online tipping system, and wonderful guides like Juliana truly deserve it. I highly recommend this tour, especially if you don’t have a car!
Our time in Montepulciano...
Jennifer H,Jun 11, 2026
- Review from Viator
5.00Our time in Montepulciano was one of our favorite days in Italy. Giovanni was an exceptional guide and he taught us so much about the wine and the area. We highly recommend Tuscan Wine Tours as they book small wineries. Our delicious lunch was at a dairy farm where we overlooked the gorgeous Tuscan region.
Amazing
abigailaV9628HH,Jun 7, 2026
- Review from Tripadvisor
5.00Me and my mom enjoyed our tour in yeahand Pienza. It was a beautiful experience and the views were breathtaking.
Fantastic day in Tuscany!
lauratD9162QW,Jun 7, 2026
- Review from Tripadvisor
5.00This was a great way to see Tuscany if you don’t have a car! I really loved the beautiful little towns we visited, driving through the countryside, and our guide Sandro who was the best. Lunch was tasty and the farmhouse we had it at was really cool. If you’d prefer to be in a small group, rather than a large tour, this one’s for you! We all got along really well, and there was ample time to explore by ourselves if we wanted to, too.
Stunning Views
Nicola R,Jun 6, 2026
- Review from Viator
5.00Had an excellent time exploring the countryside, beautiful views, plenty of food and good wine. Worth every cent.
Tutto benissimo
Catherine D,Jun 6, 2026
- Review from Viator
5.0010/10 would recommend. Keko was a knowledgeable and charismatic tour guide. While we drove through the Tuscan countryside, he provided engaging commentary about the history, the landscape, and the local food traditions of the region. If you want to see the Tuscan country, this is the way to do it. I particularly enjoyed the lunch at the farm and tasting the local recipes with ingredients made right there. The time in Pienza and Montepulciano flew by. I would definitely take this tour again.
Great Tuscan Escape
antoniodX3293AV,Jun 5, 2026
- Review from Tripadvisor
5.00Overall experience was excellent. The small group to start really worked, Sandro our guide was amazing. He was very knowledgeable and efficient. Did a great job pointing us in the right direction and answering many questions. Would definitely give him a 5 star rating. Piemza and Montepulciano are great towns. We had enough time to go around and the farm lunch was special with a full tour a great food. Would do again.
Excellent all day tour. Wonderful guid that gave great information. Very nice air conditioning van. Wonderful overlooks
Andrew S,Jun 1, 2026
- Review from Tripadvisor
5.00Excellent all day tour. Wonderful guid that gave great information. Very nice air conditioning van. Wonderful overlooks for amazing pictures. Wonderful wine and cheese tasting! Would do again for sure.
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Operated by Tuscan Escapes by Papilio SRL