Day trip

From Siena: Pienza and Montepulciano Small-Group Tour

Day trip

From Siena: Pienza and Montepulciano Small-Group Tour

Activity provider: Tuscan Escapes by Papilio
Likely to sell out

From US$ 172.42 per person

Likely to sell out

Drive through the beautiful Tuscan landscapes, and explore the towns of Pienza and Montepulciano. Enjoy a traditional lunch at a dairy farm, tour ancient cellars, and taste Vino Nobile wine.

About this activity

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Duration 8 hours
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Live tour guide
Small group
Limited to 8 participants


  • Discover the quaint medieval hamlet of Pienza
  • Sample the noble wines of Montepulciano
  • Enjoy lunch on the terrace of a local dairy farm
  • Learn the process of making Italy's famous pecorino cheese
  • Wander among the noble palaces of Montepulciano
Full description
Travel along one of the most panoramic roads in Tuscany, driving the characteristic moonscape of the Crete Senesi en route to the medieval hamlet of Pienza in the Val D’Orcia valley. One of the first towns to be entirely planned on paper by important architects and artists of the time, Pienza was commissioned by Pope Pius II - the humanist pope - to help him renovate his native town and bring it to new splendor. A wholesome lunch, based on fresh local ingredients will be waiting on a beautiful terrace (weather permitting) at a local dairy farm. Learn about the process of making Italy’s famous pecorino cheese. Continue in the afternoon to Montepulciano, one of Tuscany’s largest hill towns. Under the dominance of Siena in the Middle Ages, and Florence during the Renaissance, today it is renowned for its wine. See influences from both towns in the architecture and art of the historic center, located on a steep hill with beautiful views of the Tuscan and Umbrian border. Go to the main Piazza Grande, and tour one of the many wineries, carved out of the earth below the city. Discover some of the palaces of the noble families that once lived here. After a short walk around town with a guide, enjoy some free time to taste the fabled wines, or continue to explore the palaces, churches and streets on your own. As you follow the route of the main road downhill, imagine how hard the “Bravio delle Botti” festival must be; a competition to race wine barrels from the bottom to the top of the hill!
  • Round trip transportation by air-conditioned minivan
  • 3 course meal and pecorino cheese tasting at an organic farm
  • Cellar tour and wine tasting in Montepulciano
  • Hotel pick-up
  • Museum tickets
  • Tips and gratuities

Select participants and date



Meeting point

Meet your guide under the large tree that is in front of the Basilica in Piazza San Domenico, Siena

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Important information

What to bring

  • Comfortable shoes

Know before you go

  • Comfortable walking shoes are recommended.
Customer reviews

Overall rating

5 /5

based on 44 reviews

Review summary

  • Guide
  • Transportation
  • Service
  • Organization

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Star rating:

This tour was incredible. Our tour guide (Elio) made the trip! He was informative, personable and funny. I would highly recommend this full day trip to enjoy all the tour has to offer without feeling rushed. I am looking to see what other tours I could possibly take with Elio while we are here!

March 26, 2023

The one day tour was a great way to visit Pienza and Montepulciano. Though I would have liked more time in each place there are only so many hours in a day The guide was extremely passionate about the area and full of information. The only downside was the winery we went to in Montepulciano, The wine was excellent so I made a purchase of some wine to be delivered overseas. Since returning home I have had no correspondence from the winery even though I sent a request via instagram, one request via their site and 4 emails with copies of the sales documents. So it looks as though I have lost my 171.00 Euro.

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March 26, 2023

Very enjoyable day, from the moment we met our very engaging, knowledgeable and entertaining guide Ambra, getting to know the others on the tour, visits to lovely places including lunch, wine tasting, sightseeing and the drive back to Siena from Multipulciano a truly great experience!

March 26, 2023

Product ID: 47141