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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

Lisa O

5 star rating: Highly Recommended January 2017

Elena was a fantastic tour guide. Fortunately, my boyfriend and I were the only people on the tour that day so we got a lot of undivided attention. We definitely felt like we'd gotten the special treatment!
Elena met us, on time, at our designated pick-up spot and quickly whisked us off toward Pienza. We stopped at a little village along the way for a cup of coffee she refused to let us pay and a bit of sightseeing. From there we headed to a farm for lunch one of our favorite locations/experiences of our entire two weeks in Italy and then into Pienza proper. What a beautiful town! Elena walked us through the town, giving us great historic information, and then allowed us to wander leisurely for the rest of our time there.
On our way to Montepulciano, Elena was kind enough to pull over, allowing me to capture some of the breathtaking landscape with my camera. Once we arrived in Montepulciano she again walked with us to give us historical insight, but then gave us time to take in the town at our own pace.
Upon our return to Siena she was kind enough to drop us off closer to our apartment rather than the designated drop off point which was so appreciated after a long day of touring.
Do not miss these two towns when you're in Tuscany - and this Viator tour was the perfect way for us to experience them! We never felt rushed and we probably wouldn't have seen half of the wonderful sights we were shown had we driven there on our own.

Judy G

5 star rating: Highly Recommended January 2017

This is my second attempt to post a review. My husband and I are still raving about our wonderful tour with Sylvia in October. It was a fabulous day and one of the highlights of our entire trip. The tour was perfectly timed, beginning with a coffee stop in charming little Chiusure, anchored by an unforgettable meal at the biodynamic farm, and finishing just as the rain began in Montepulciano. Sylvia was a delightful host and the tour exceeded our expectations.


5 star rating: Highly Recommended December 2016

My favorite trip in Italy. The towns of Montepulciano and Pienza were charming. And the farm/restaurant was amazing -- some of the best food we had in all of Italy. Very enjoyable trip.

John K

5 star rating: Highly Recommended November 2016

We met our friendly guide in Siena as well as the other 5
Travelers. We spent a wonderful day exploring
Southern Tuscany. Each stop was unique and
An opportunity to meet local residents and experience
The ambience of the area. The lunch under the Tuscan sun was
Delicious and congenial! We loved this our first full day in

Brian C

5 star rating: Highly Recommended October 2016

Fabulous! We enjoyed the size of the small group tour 7 and give Mary kudos for a job well done. Lunch was amazing! We even visited a tourist-free village!! Had lots of fun and would definitely recommend this trip. The views were breath-taking. Sadly, have tried to post photos without success. JC

David D J

5 star rating: Highly Recommended October 2016

An excellent tour led by a guide Elena? who was personable, knowledgeable, energetic, and passionate about the places she took us. The areas we visited were beautiful and interesting, and the tour was easily the best among the ones we took during our three weeks in Italy. Loved the fact that the tour was small, too, and we had a chance to interact with the guide, who seemed happy to answer every question she was asked.

Karen S

5 star rating: Highly Recommended September 2016

We had a wonderful day!
Mare was a delightful guide with lots of knowledge of the area.


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!

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