• Location: Siena, Italy
  • Duration: 8 hours (approx.)
From USD $ 164.94 View price calendar

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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

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

Tat A

5 star rating: Highly Recommended January 2018

A combination of sightseeing and wine tasting. Loved it.

Dabay United States of ... 

5 star rating: Highly Recommended October 2017

Wow - if I could give more stars, I would! This was definitely the highlight of our trip to Italy across Rome, Venice, Florence, and Siena. Corrado was an amazing guide, and took us through the rolling countryside of southern Tuscany, to small towns I'd only dreamed of. The views were breathtaking, and the farm lunch was so perfectly quaint and yet awe-inspiring the views were unreal! Visiting Pienza and Montepulciano was my dream come true, and I wish I could have spent more time in both beautiful towns. I can honestly say this was one of the top 5 days in my life - it was a once-in-a-lifetime experience, and the tour company took all of the guesswork out of the equation so we could truly relax and enjoy. I cannot recommend this tour enough.

Vickie C

5 star rating: Highly Recommended October 2017

What a fantastic day. Would highly recommend as the small group makes it so nice and personal. We had a great day seeing all the beautiful scenery and a WONDERFUL farm to table lunch in a fantastic spot. Nice to have a bit of free time to shop and walk Pienza as well.


5 star rating: Highly Recommended October 2017

Beautiful tour and very friendly guide. 2 very special places you must see and the countryside drive is very pleasant.


5 star rating: Highly Recommended October 2017


Shiree R

5 star rating: Highly Recommended May 2017

Elena was such a great tour guide. Our pickup was easy, the tour was informative and very interesting in all 3 locations. We stopped in an enchanting small village on the way to Pienza, it was gorgeous. There was enough time to walk about on our own in both Pienza and Montepulciano. The farm to table restaurant we had lunch at was absolutely stunning. I thoroughly recommend this tour to anyone.


5 star rating: Highly Recommended April 2017

Loved this tour, our tour guide Elena was awesome, She was fun, knowledgeable and helpful. We loved the tour of the Tuscan countryside, what gorgeous, picturesque landscapes. We really enjoyed the town of Pienza, the whole town smells of cheese!!! In a good way : After Pienza, we went to an organic farm that made everything we ate and drank, it was delicious! We then went to Montelpulciano for a wine cave tour and a wine tasting. The wine was fantastic, so happy we ordered some!
the whole day was lovely!

Ruth F

5 star rating: Highly Recommended April 2017

Elena was well-informed, enthusiastic and ensured we had a good time. The food/drink was excellent and the views beautiful. We had a wonderful day.

Stephen K

5 star rating: Highly Recommended March 2017

Thought the owner/driver who picked us up and took us around was excellent...he was interesting, spoke perfect colloquial English and was ultra-knowledgable, which is refreshing and was well-received by my wife and myself. The tour highlights the two areas, Pienza and Montepulciano, with an amazing, organic lunch on the way and lots of knowledge to soak in. No fluff, all fun. Just right

Larry K

5 star rating: Highly Recommended March 2017

My husband and I went on this tour on a rainy day last week. Despite the weather, the scenery was beautiful, towns were enchanting and lunch was spectacular. Milo was a great tour guide, giving us interesting information and pointing out fantastic sights.The family who provided us with a delicious, organic lunch were lovely and very warm and welcoming.

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