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
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
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
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.
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Small-Group Montepulciano and Pienza Day Trip from Siena
Reviews
278 reviews
Total reviews and rating from Viator & Tripadvisor
A great day in Tuscany!
Mark Y,
Nov 6, 2025
- Review from Viator
5.00We had a wonderful day with our amazing and awesome guide, Daniele. He was extremely knowledgeable and informative and personable. He shared bits of history and interesting facts about the area. His knowledge of wine and it’s production is impressive. He’s a true connoisseur of great wine. A little bit of a long day but worth every minute. We returned to our meeting point at about 6:15pm. I highly recommend this trip!
Amazing experience!
andrewtM710VF,
Nov 3, 2025
- Review from Tripadvisor
5.00Mattea was freaking phenomenal and led an action packed day of seeing to a of sights of Tuscany. He was fun to be around and got the group connecting and chatting which led to everyone having a good time
Highlight tour of Tuscany
Janet B,
Nov 1, 2025
- Review from Viator
5.00Guiliana is an expert guide, making our trip so interesting. She is an absolute rock star! She knew so much history about the area and answered any questions we had. The views through the winding roads on our trip to Pienza and Montepulciano were spectacular. After stopping for a cappuccino in a little town along the way, we were able to explore Pienza. It rained during our time there, but we made the best of it by having a delicious lunch at a nearby cheese farm, Podere Il Casale. We were served various cheeses to try from mild to very strong, salad, and a pasta dish. Perfect. We also learned about the differences of olive oil. With our bellies full, we headed to wine tasting at the Gattevecchi winery. We were given a tour of their wine cellar, too. Even though it was raining really hard, we still managed to walk through the town of Montepulciano. This tour is a must if you want to learn more about the Tuscany region. Be sure to ask for Guiliana as your guide!
Great driver!felt so safe
toniannes144,
Oct 31, 2025
- Review from Tripadvisor
5.00Our tour guide Julianna was amazing. First she was a great driver. We felt very comfortable driving with her. The day unfolded so nicely. We stoped at several scenic stops along the way. First long stop was Pienza. What a spectacular small city. Afterwards we at lunch at a small farm that produced local cheeses. The meal and wine were fantastic! Fresh and organic. The olive oil was spectacular! Next we went to a local winery and then Montipuciano . Wonderful day wonderful experience! I highly recommend it!
A wonderful day in Tuscany
sandymak1,
Oct 28, 2025
- Review from Tripadvisor
5.00Our guide Keko was fantastic - full of energy and lots of interesting stories. The countryside is spectacular and Montepulciano and Pienza are spellbinding. The lunch was delicious with again, wonderful views. We had the best day
A great day in the heart of Tuscany!
markmS9837YT,
Oct 27, 2025
- Review from Tripadvisor
5.00Our 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!
A very relaxing way to see the Tuscan countryside and towns
Getaway725709,
Oct 26, 2025
- Review from Tripadvisor
5.00What 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.
Highly recommend.
Cindy D,
Oct 25, 2025
- Review from Viator
5.00Claudia was amazing. Terrific day; so informative and fun. She was personable and well versed in history and wine.
Ticked all the boxes.
Cristine E,
Oct 24, 2025
- Review from Viator
5.00Excellent. So easy to let someone else do the driving. The guide provided great information. Considered the groups’ needs.
Exceptionally good small tour company
Hatbox,
Oct 22, 2025
- Review from Tripadvisor
5.00I’ve given the same review for the day tour to San Giminiano and Volterra . I went with a different guide but he was also absolutely first class. This is an exceptionally good small tour company. I can not recommend them too highly
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