Tuscan Dream Day: Montepulciano & Pienza from Siena
Price From $177.84 per person
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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.
Reviews
Reviews and Rating (Tripadvisor)
5 stars
Reviews by Tripadvisor travelers
andrewtM710VF, 11/3/2025 1:03:19 PM
Mattea 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
Janet_B, 11/1/2025 4:55:59 AM
Guiliana 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!
toniannes144, 10/31/2025 12:23:22 PM
Our 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!
sandymak1, 10/28/2025 4:58:10 AM
Our 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
markmS9837YT, 10/27/2025 4:42:22 AM
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!
Getaway725709, 10/26/2025 12:41:40 PM
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.
Cindy_D, 10/25/2025 8:18:59 AM
Claudia was amazing. Terrific day; so informative and fun. She was personable and well versed in history and wine.
Cristine_E, 10/24/2025 11:28:34 AM
Excellent. So easy to let someone else do the driving. The guide provided great information. Considered the groups’ needs.
Hatbox, 10/22/2025 5:10:52 AM
I’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
Sandra_L, 10/20/2025 3:19:21 AM
Our guide, Marco, is very knowledgeable, personable and friendly. He shared a wealth of information with our group and answered all of our questions. The van was comfortable and Marco made it a very comfortable drive. It was wonderful to see the countryside and views, and have time to explore a couple of the towns along the way. The stop at the dairy farm was amazing - the view is breathtaking and the lunch was delicious. I booked this trip for my adult daughters and I - we all really enjoyed the day and are glad Marco was our host. We would highly recommend this for others looking for a small tour of Toscana!
- 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
Departure 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.Return details
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.No redemption information available
24 hours before travel date - 100% refund
Less than 24 hours before travel date - 0% refund








