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Small-Group Montepulciano and Pienza Day Trip from Siena

icon 8 hours Mobile ticket Free Cancellation
Tickets from € 288.00

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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 protected landscapes of Tuscany's charming Val d’Orcia region. Explore the beautiful towns, enjoy the landscapes and have lunch on a local farm! Numbers are limited to a maximum of 8 persons on this small-group tour, ensuring you'll receive personalized attention from your guide.
  • Transport by air-conditioned minivan (maximum 8 passengers)
  • Lunch on local farm with wine
  • Alcoholic Beverages
  • Driver/Guide
  • Hotel pickup and drop-off
  • Gratuities
Departure Point

Piazza S. Domenico, 1, 53100 Siena SI, Italy Meet your guide in front of the church of San Domenico in Siena at 9:30am, easy to find even if you are arriving from out of town with your own car, as there is parking in the vicinity.

Return Details

Piazza S. Domenico, 1, 53100 Siena SI, Italy Meet your guide in front of the church of San Domenico in Siena at 9:30am, easy to find even if you are arriving from out of town with your own car, as there is parking in the vicinity.

  • Basilica Cateriniana Di S. Domenico, Siena, Italy
    Meet your guide in front of the church of San Domenico in Siena at 9:30am, easy to find even if you are arriving from out of town with your own car, as there is parking in the vicinity. Travel south out of town on one of the most panoramic roads of Tuscany, through the characteristic moonscapes of the Crete Senesi.
  • Chiusure, 53041 Chiusure SI, Italy
    Enjoy brief stops along the Crete Senesi for for photo opportunities before visiting a quaint, non touristic medieval hamlet. Continue along this stunning landscape and reach the UNESCO heritage site of the Val d’Orcia, where you come across some of Tuscany’s most iconic postcard pictures.
    30 minutes
  • Historic Centre of the City of Pienza, Pienza, Italy
    Arrive to the beautiful, utopian renaissance town of Pienza, one of the first towns to be entirely planned out on paper by important architects of the time. These were called upon by Pope Pius II, the humanist pope who wanted to renovate his native town and bring it new splendor.
    60 minutes
  • Il Duomo di Pienza, Pienza, Italy
    Spend your leisure time exploring the Romanesque church of Corsignano or the ideal, Renaissance Cathedral and walk along the scenic route overlooking the valleys and hills beyond. Browse the pretty streets of this gem of a town or some of its many shops of local crafts and products.
    15 minutes
  • Val d'Orcia, Italy
    Visit a val d'Orcia dairy farm for a wholesome and refreshing lunch based mainly on the fresh ingredients produced on the farm. Here you can learn about the pecorino sheep cheese making processes, visit the farm animals and learn about the lifestyle of the area. Weather permitting, lunch will be served on a panoramic terrace, overlooking the valley below.
    60 minutes
  • Montepulciano, Montepulciano, Italy
    In the afternoon, visit one of the biggest and proudest of the Tuscan hill towns, Montepulciano. This town was first under the dominance of medieval Siena and then became an ally to renaissance Florence: here you can recognize the influences of both Republics in its architecture and art. Located on a steep hill, you can look over the ledge at the the Tuscany - Umbrian border.
    60 minutes
  • Piazza Grande a Montepulciano, Montepulciano, Italy
    Visit the main square, Piazza Grande, and explore one of the many old wineries carved out of the ground below the city, and taste the Vino Nobile that was produced by the many important and noble families that one lived here.After a short walk around town with your guide, enjoy some free time on a second tasting of the Nobile wine or visit the town’s many stores, palaces, churches and streets. As you follow the main road down the hill, imagine how hard the “Bravio delle Botti” town festival must be: a competition between the neighborhoods of the town that race wine barrels from the bottom of the hill, all the way to the top. On some occasions the itinerary might vary a little. In this case, the tour could be slightly modified but will maintain a similar general imprint, of the same duration and with all the same inclusions.
    30 minutes
  • Infants and small children can ride in a pram or stroller
  • Public transportation options are available nearby
  • Specialized infant seats are available
  • Not recommended for travelers with poor cardiovascular health
  • Suitable for all physical fitness levels
  • Customers who have not reached Italy's legal drinking age of 18 will not be served alcohol
You can cancel up to 24 hours in advance of the experience for a full refund.
  • For a full refund, cancel at least 24 hours before the scheduled departure time.
  • If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the experience’s start time will not be accepted.
  • Cut-off times are based on the experience’s local time.
  • This experience requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund.
Karen_O
10 May 2025
Lovely Tuscan towns. Great lunch. Wonderful guide. I have nothing else to say so writing this rubbish to satisfy requirement.
Barbara_R
10 May 2025
Guillermo was outstanding and is the most knowledgeable, articulate and entertaining tour guide we’ve experienced in a long list of great tour guides in Italy. His special energy kept us fresh and engaged for the entire 8 hours. We highly recommend him!!!
24gregj
06 May 2025
Splendid day and beautiful Tuscan countryside. Marco was so hospitable and informative as well as being a delightful person. The tour was well planed and even better as executed I highly recommended. Pienza and Montepulciano are exactly the Italy we were seeking. Can not go wrong with this excursion
This tour in Tuscany is organized by Tuscan Escapes by Papilio

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