Small-Group Montepulciano and Pienza Day Trip from Siena

We had a wonderful day in May 2022 with Marella on this tour. She showed us all sorts of interesting places and views. We booked this instead of renting a car, and we were glad we made that decision. Marella was a lot of fun to spend the day with, she took us to places we would not have selected on our own, and we didn't have to deal with directions and a designated driver. Some of the highlights were the tiny village where we first stopped for coffee, the great lunch, and Piensa. The winery in Montepulciano was interesting because the caves were so old (from the Etruscan era), but the wine itself was just so so and the place was uncomfortably crowded. All in all, this "small-group" tour, which turned out to just be the two of us, was one of the best days on our Italy trip.

This was our 1/3 trips led by Georgia. She was so attentive and Knowledgeable as a tour guide, and incredibly charming as a person. Tours of Montepulciano and Pienza were mostly self-led, but it worked out well because she took us to the most important sites and told us about the history of the towns and what to look for during the car ride there. We had a lot of fun and 100% recommend this tour!

Incredible day trip! We couldn’t have had a better guide, the views were phenomenal and the lunch was even better than expected.

What an extraordinary day from start to finish. Our group had a lovely drive through the hills stopping in a little town for coffee. Both Pienza and Montepulciano are beautiful each in their own way. We had enough time to walk around and see the main streets and a few little side alleys. Every few feet was a postcard view. Incredible. The included lunch was very good and after we had a quick visit with some of the animals on the property. Our guide was terrific and gave us a lot of information along the drive and as we arrived in each town. The whole tour process works well. The meet up at the church went quickly and we were dropped off there at the end of the day. I purposely chose a hotel a 2 minutes walk from the meeting point since my three full days in Sienna included two days on these small group tours with this company. Overall I thinks it's very good value for the money. Small tours allow more conversation among the group, more opportunity to ask the guide questions, and the small vans can drop you off close to the walled towns and quickly maneuver through traffic better than giant tour busses.

Our guide Georgia was Amazing! She was so knowledgeable and very interesting to listen to. The trip left from Siena. The views of the Tuscan area was Outstanding, the farm to table lunch was the best part of the trip. Would do this trip again!

We had a lovely day with our tour guide, Ambra! I could have skipped the stop for tea/coffee in Asciano so that we could have more time in Pienza and Montepulciano, but we knew when we booked the trip that our time there would be limited. We enjoyed lunch on the patio at the pecorino farm. The view was absolutely beautiful! Lunch was light but good (but no meat). I was surprised that the pasta was a cold rotini salad from pre-made pasta---not the fresh pasta you'd expect in Italy. Ambra made the trip special. We stopped in several places so she could take photos of us. She is passionate about Italian history and culture and we really enjoyed talking to her. We took another Tuscan Escapes trip the next day and also had a good experience. I think their trips are a good way to see the countryside and explore hill towns if you don't have a car and don't want to deal with public transportation.

We had a lovely day trip from Siena to Pienza and Montepluciano with TuscanEscapes Tours. The eight hour tour included an unbelievable lunch stop at Podore I’ll Casale along with a nice visit to Pienza and Montepluciano. Our guide was very cool and fun to be with as well as very knowledgeable. Lastly, we had a fun wine tasting De’Ricci in Montepluciano and was able to learn a lot about the historic building and wine making family. A wonderful day!

Tour guide should have known that the bathroom was near the bus instead of sending me all the way back up the main street.

Ambra was a terrific guide — informative and fun! We enjoyed every stop — especially lunch on the farm!

The trip was amazing! Pienza is a beautiful town! Our tour guide Elena was excellent, so knowledgeable and so nice. The lunch destination was almost heaven! Delicious food and the best views in all of Tuscany! I highly recommend this tour you will not be disappointed!