Small-Group Montepulciano and Pienza Day Trip from Siena

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 lunch and taste Pecorino cheese 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.

per adult from




8 hours


Mobile ticket

Select Date and Travellers

No tour options available.

  • What's included :
    • Driver/Guide
    • Transport by air-conditioned minivan (maximum 8 passengers)
    • Cheese tasting
    • Lunch
    • Alcoholic Beverages
    What's excluded :
    • Hotel pickup and drop-off
    • Gratuities
  • This is a typical itinerary for this product

    Pass By: Basilica Cateriniana Di S. Domenico, Piazza San Domenico, 53100, 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.

    Stop At: 53041 Chiusure Province of Siena, 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.

    Duration: 30 minutes

    Stop At: Historic Centre of the City of Pienza, near Montepulciano 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.

    Duration: 1 hour

    Stop At: Il Duomo di Pienza, Piazza Pio II, 2, 53026, 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.

    Duration: 15 minutes

    Stop At: 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.

    Duration: 1 hour

    Stop At: Montepulciano, Montepulciano, Tuscany

    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.

    Duration: 1 hour

    Stop At: Piazza Grande a Montepulciano, Pazza Grande, 53045, 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.

    Duration: 30 minutes

  • Departure Point :
    Basilica Cateriniana San Domenico, Piazza San Domenico, 1, 53100 Siena SI, Italy
    Departure Time :
    9:30 AM
    Return Detail :
    Returns to original departure point
    Hotel Pickup :
    • 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
    • Most travelers can participate
    • 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
    • This tour/activity will have a maximum of 8 travelers
    • Face masks required for travelers in public areas
    • Face masks required for guides in public areas
    • Hand sanitizer available to travelers and staff
    • Social distancing enforced throughout experience
    • Regularly sanitized high-traffic areas
    • Gear/equipment sanitized between use
    • Transportation vehicles regularly sanitized
    • Guides required to regularly wash hands
    • Regular temperature checks for staff
    • Paid stay-at-home policy for staff with symptoms
    • Tours are operated in 9 seater vans but a max. of 5 participants will be accepted on tour to ensure social distancing. All travelers will have to wear their own personal protective equipment (masks covering nose and mouth).
  • You can present either a paper or an electronic voucher for this activity.
  • For a full refund, cancel at least 24 hours in advance of the start date of the experience.



Age Req.


Fitness Req.


Group Size


Organised by Tuscan Escapes by Papilio


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