Tour code: 5493MONTEPULCIANO
Discover Tuscany's stunning landscape, culinary delights and UNESCO-listed sites on a day trip to Montepulciano and Pienza from Siena. Led by a local guide, admire the architectural gems of the Val d'Orcia region and stop at a dairy farm for lunch and samples of salty Pecorino cheese. Conclude your trip in the scenic hill town of Montepulciano, with an optional visit to a winery. Group size is limited to eight people, ensuring 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


Begin your day trip with pickup in Siena, where you’ll hop aboard your minivan and travel toward Pienza with your guide. Pass through the Crete Senesi along the way, clay hills with a lunar-like appearance as a result of the soil’s gray coloring. 

Arrive in the town of Pienza, the gem of the UNESCO-listed Val d’Orcia region. Enjoy some free time to explore here independently, strolling the streets or perusing the local shops.

Head next to a dairy farm for a delicious lunch made from the farm's fresh ingredients. Treat your taste buds to a sampling of salty Pecorino cheese, a favorite in Italy, and hear about the farm’s history and production process.

Continue to Montepulciano, a hill town overlooking the scenic Tuscany-Umbria border. Take a guided stroll around the Piazza Grande before wandering the churches, palaces or stores at your leisure. On request, make an additional stop at a winery for a tour of the cellars and tastes of Montepulciano’s celebrated vino.

After a full day of fine food and exploration, your tour will conclude with transportation 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

From USD $ 159.08

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