5 star rating: Highly Recommended 28 Reviews

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  • Location: Siena, Italy
  • Duration:  8 hours (approx.)
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-listed landscapes of Tuscany's charming Val d’Orcia region. Explore the beautiful towns, enjoy lunch and taste Pecorino cheese on a local farm!

Numbers are limited to eight people on this small-group tour, ensuring you'll receive personalized attention from your guide.


  • Guided full-day trip to Montepulciano and Pienza from Siena
  • Drive through the magical landscapes of the Crete Senesi
  • Discover the Val d'Orcia, a UNESCO World Heritage Site
  • Savor lunch and a Pecorino cheese tasting (included) on an organic dairy farm with spectacular views
  • Small-group tour with a maximum of eight people ensures an intimate experience

Recent Photos of This Tour

What You Can Expect

Small-Group Montepulciano and Pienza Day Trip from Siena


Meet your friendly guide in central Siena and head out of town in a comfortable minivan on one of Tuscany's panoramic roads, passing through the characteristic clay hills known as the Crete Senesi. Arrive first in the beautiful town of Pienza, which was entirely planned out by Pope Pius II, the humanist pope, to be the ideal Renaissance town.

Pienza is rightly considered the gem of the Val d’Orcia region; the town and the entire Val d’Orcia are World Heritage Sites. You'll have time to spend at leisure here, so make the most of it by shopping or exploring the pretty alleyways of this small town at your leisure. As you leave Pienza, enjoy the fantastic views of Tuscany’s famous picture-perfect scenery.

Your next stop is a local dairy farm, where you’ll feast on a wholesome and refreshing lunch (included) of fresh ingredients mostly produced on the farm. You’ll also enjoy a tasting of Italy’s salty Pecorino cheese, hear about the cheese-making process, visit the farm’s animals and learn about the lifestyle of the area.

In the afternoon, travel to Montepulciano, one of Tuscany’s biggest hill towns, located on a steep hill overlooking the amazing landscape of the Tuscany-Umbria border. With your guide, take a short walk around town to see the Piazza Grande at the top of the hill. You’ll then have free time to visit the town’s many stores, palaces or churches. On request, visit a winery to enjoy a tasting of Montepulciano’s renowned wine and tour the wine cellars before your relaxing ride back to Siena.

Customer Reviews

5 star rating: Highly Recommended June 2015

We had a wonderful time!

5 star rating: Highly Recommended June 2015

Our guide Elena was amazing-warm, very knowledgable. We learned a lot about the history of the region and enjoyed beautiful sights.

5 star rating: Highly Recommended June 2015

Elena was an excellent and friendly guide. The towns and countryside were beautiful and lunch good cheese was excellent.

5 star rating: Highly Recommended June 2015

Milo was an excellent, informative and entertaining guide, and the trip was a very good mix of drive through beautiful countryside, delightful hill towns and superb leisurely lunch at the organic farm, along with good wine. The wine tasting in Montepulciano was unexpected and very enjoyable.

5 star rating: Highly Recommended May 2015

Did this tour last year and enjoyed it so much came back for more
An absolute must to see the best of the Tuscan hill towns and enjoy an excellent lunch with all produce coming from their own farm
Elena was both helpful and knowledgable

5 star rating: Highly Recommended May 2015

Lot's of fun and informative!

5 star rating: Highly Recommended May 2015

This was an excellent trip and Elena our Tour Guide was excellent. She was very fluent in English and went out of her way to make this an amazing, special tour!!! She was very well versed in all sorts of topics and she was able to answer our many and varied questions. I think the highlight of the day was the lunch in a fabulous restaurant where we ate Italian food and she showed us how to eat it the Italian way. Well done Elena!!!

5 star rating: Highly Recommended May 2015

If you are in Siena, you have to take this tour! The visit to the dairy farm was wonderful. Silvia, our tour guide, made the experience personal and unique.

5 star rating: Highly Recommended November 2014

We found our trip extremely worthwhile. Milo was knowledgeable, pleasant, and we learnt a lot regarding Montepulciano, Pienza and Italy in general. He knew his subject well and had a fun way of imparting this. Would recommend this trip to everyone.
S. and J. Jacobsohn

5 star rating: Highly Recommended October 2014

This was so much fun! I absolutely loved Pienza. Montepulciano is pretty nice but Pienza was the real highlight for me. The farm restaurant that we had lunch at was fantastic. We had some really delicious food - and lots of it too! Our guide was Daniel and he was very friendly and knowledgeable.

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Tour code: 5493MONTEPULCIANO


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