Day trip

From Siena: Pienza and Montepulciano Small-Group Tour

From Siena: Pienza and Montepulciano Small-Group Tour

Activity provider: Tuscan Escapes by Papilio
Likely to sell out
Likely to sell out

From US$ 168.87 per person

Drive through a beautiful Tuscan landscape on an 8-hour tour from Siena, and see the characteristic villages of Pienza and Montepulciano, renowned for its wines. Enjoy a traditional lunch at an organic dairy farm, and tour ancient wine cellars.

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
  • Tour one of the historic wine cellars, carved out of the landscape
  • Travel along the moonscape road of the Crete Senesi
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!
  • Live tour guide
  • Transport for activity duration: Van
  • Lunch
  • Water
  • Alcoholic drinks
  • Alcoholic drinks
  • Water
    Covid-19 precautions
    Safety measures in place
    • All areas that customers touch are frequently cleaned
    • You must keep social distance while in vehicles
    • The number of visitors is limited to reduce crowds
    Traveler requirements
    • You are required to bring and wear a mask

    Select participants and date



    Meeting point

    Meet at the Basilica of San Domenico, Siena

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    Customer reviews

    Overall rating

    5 /5

    based on 33 reviews

    Review summary

    • Guide
    • Transportation
    • Value for money
    • Safety

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    What an amazing day - Elio made this adventure in Tuscany a highlight of our recent European holiday. He started the day by finding out our interests and then tailor-made the sights & activities above our expectations. His local knowledge and descriptions of places of interest in his musical Italian accent brought each place we visited to life. And the farm lunch was yet another highlight - all 4 courses & the wine were produced on farm and each part was fully explained. Elio drove us at a comfortable speed in a modern fully air conditioned van. Thanks again Elio was such a memorable day

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    July 1, 2019

    Marella is a Tuscany gem!

    This tour with Marella through the countryside, small towns, Pienza, Montepulcino, was very genuine and authentic. I would book more tours with Marella and Tuscan Escapes, we learned so much about Tuscany and she really has a passion for sharing the culture and unique experiences that you cant get anywhere else, genuine, authentic Tuscan lifestyle experiences, history and stories.

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    May 14, 2019

    I loved the trip to Pienza and Montepulciano!Special places, with views

    Due to the practicality of having a local guide, without the stress of having to drive in another country, I think it was worth taking this tour for a maximum of 8 people. Guide with good knowledge of the places. local. I have a reservation about the wine tasting place we visited! The cellar itself is very interesting, but the wines tasted were horrible! The wines at the entrance to the winery! Not worth buying! As for going to a local farm for lunch, it was well interspersed with the cheeses at the start, and again I make exception to the rose wine service at lunch! A red wine could have been served and in greater quantity. It was only given throughout lunch (entry +pasta+dessert) a single glass of rose wine. The rest of the trip, stops for photos and visits were excellent. Wonderful view of the entire Val d'Orcia, including the cities of Pienza and Montepulciano! Lively group, excellent guide. Would do it again !

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    May 14, 2019

    Product ID: 47141