5 star rating: Highly Recommended 34 Reviews

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  • Location:Siena, Italy
  • Duration:8 hours (approx.)

Small-Group Montepulciano and Pienza Day Trip from Siena

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 November 2015

This was a beautiful sunny day in November. We spent eight wonderful hours touring Tuscany, two beautiful hill towns and having a stunning lunch at a private residence over looking the Tuscan countryside, a scene out of a movie, and we were in it. Our tour guide was very friendly and informative. We were very lucky to be the only people on our tour off season and had plenty of time to explore on our own. I would highly recommend this tour.


5 star rating: Highly Recommended October 2015

It was a lovely tour. We especially enjoyed the wine tasting experience, which was informative and entertaining.

James C

5 star rating: Highly Recommended September 2015

Sylvia as our tour hostess was totally awesome! This was the best deal of any tour we have hired in the past bar none. We saw a lot of the beautiful Tuscan country and towns. We had a meal to die for at an organic farm where everything was produced on the farm: wheat/flour/bread, red and white wine, various cheeses, and fresh vegetables. It will be well remembered and talked bout in our household. Thanks Viator!

Douglas P

5 star rating: Highly Recommended September 2015

A beautiful tour on a gorgeous day in Tuscany. Our guide Sylvia was superb! She facilitated what evolved into a wonderful dynamic within our small group of tourists. Please compliment our guide.

Matthew M

5 star rating: Highly Recommended September 2015

After traveling to Italy 14 times, I came across the most knowledgeable, gracious and thoughtful tour guide I have ever known. Bravo Viator!!


5 star rating: Highly Recommended June 2015

We had a wonderful time!

Viktoriya B

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.

Hilary C

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

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Tour code: 5493MONTEPULCIANO


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