Small-Group Montepulciano And Pienza Day Trip From Siena

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Tour Information

Key Details

  • Mobile Voucher Accepted
  • Instant Confirmation
  • Lowest Price Guaranteed
  • Duration: 8 Hrs
  • Language:
  • Departure Time :
    09:30 AM
  • Departure Details :
    Basilica Cateriniana San Domenico, Piazza S. Domenico, 1, 53100 Siena SI, Italy
  • Return Details :
    Returns to original departure point
  • Cancellation Policy :
    This activity is non-refundable Tours booked using discount coupon codes will be non refundable.


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 dOrcia 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.


  • Great overview and orientation of the city
  • Informative, friendly and professional guide
  • Perfect introduction for first-time visitors

Know More about this tour

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 dOrcia region; the town and the entire Val dOrcia 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 Tuscanys famous picture-perfect scenery.

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

In the afternoon, travel to Montepulciano, one of Tuscanys 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. Youll then have free time to visit the towns many stores, palaces or churches. On request, visit a winery to enjoy a tasting of Montepulcianos renowned wine and tour the wine cellars before your relaxing ride back to Siena.



Transport by air-conditioned minivan (maximum 8 passengers)

Cheese tasting


Alcoholic Beverages


Hotel pickup and drop-off


Additional Info

Confirmation will be received at time of booking, unless booked within 16 hours of travel. In this case confirmation will be received as soon as possible, subject to availability

Customers who have not reached Italy's legal drinking age of 18 will not be served alcohol

Not wheelchair accessible

Stroller accessible

Near public transportation

Infant seats available

No heart problems or other serious medical conditions

Most travelers can participate

This experience requires a minimum number of travelers. If its canceled because the minimum isnt met, youll be offered a different date/experience or a full refund

This tour/activity will have a maximum of 8 travelers

All travelers will have to wear their own personal protective equipment (masks covering nose and mouth).

Traveler Reviews

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  • 26-Oct-2022

    Guide was very helpful. Visited the countryside, small village, great vistas, lovely outdoor lunch with more views and wine. Pienza and Motepulciano are beautiful historic towns. Wine tasting was great. Perfect day

  • 25-Oct-2022

    This tour is wonderful. You simply can't ask for a better full day out in the countryside. I book this tour every time I'm in the region (this most recent trip was my fourth time) and it never disappoints! This time I brought along my mom and sister for the day; Georgia was our guide and she was amazing, of course. She was engaging and fun and with an art history degree, very knowledgeable! I know when I'm booking a Tuscan Escape day tour, I'm in for a real treat. If you're into good company, knowledgeable guides, fantastic food, quaint towns and breathtaking scenery, this tour is for you!

  • 19-Oct-2022

    Our Italian guide “William” was excellent. Very knowledgeable, fluent in English though very Italian that he is. Lunch at an organic farm with fabulous view was a highlight for me. There was enough time to visit the towns too. Highly recommend

  • 14-Oct-2022

    The whole day was thoroughly enjoyable. Guillermo was terrific..knowledgeable and fun. Great stops with enough free time to explore. Loved Pienza, the farm and Montepulciano. Highly recommended.

  • 13-Oct-2022

    We had a perfect day with our tour guide, Ambra! She showed took us to all sorts of interesting places and views! This was a perfect way to see the rolling Tuscan hills and countryside without the worry of renting a car. We first stopped for coffee at a tiny town, to break up the drive. Then had pecorino cheese tasting at a farm outside of Piensa and a wonderful zucchini spelt dish for lunch. Piensa was definitely our favorite Tuscan town, postcard views everywhere you looked! Highly recommend the tour!

  • 04-Oct-2022

    We learned so much about Tuscan, history and culture, while sampling, its rich landscape, food, and wind. Our guide, William, gave us such an inspiring introduction to the place. He obviously loves so much.

  • 30-Sep-2022

    The rolling hills of Tuscany.. idyllic little towns. Great food! A terrific guide and driver in Georgia. Tuscan Escapes is a fabulous option for this magnificent tour of a piece of heaven on earth.

  • 13-Sep-2022

    The guide was very knowledgeable. The views were amazing, and the towns were lovely. The lunch with cheese tasting was delicious!

  • 23-Aug-2022

    This trip was absolutely divine. My trip to Siena would not have been the same without it. I had never been to Italy before this trip, and I was looking for something structured to do so I could get a more in depth taste of the Tuscan countryside. Our tour guide Guillermo was kind, fun, intelligent, and an all-around great guy. I can't thank him enough for making this experience a unique one. He shared interesting facts and histories about the area, and he was so attentive to what we as a group wanted to do to have a good time. Pienza was stunning to stroll through, and my group elected to do the wine tour in Montepulciano (which I would highly recommend). The views throughout this entire excursion were absolutely breathtaking. Eating at the organic farm remains one of my favorite dining experiences from my entire vacation because of the fresh food and atmosphere. This trip was a great value and made especially wonderful by Guillermo.

  • 19-Aug-2022

    Had such a great day with Mattia learning about towns near Siena and the history of wine in the region. He was a wonderful tour guide and knew so much about the region, its history, and its wines. Highly recommend.

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