Small-Group Montepulciano and Pienza Day Trip from Siena

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.

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, 53026, 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.

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

Informacion Adicional
"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 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"
"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"

Hora de Inicio: 09:30 AM
Duración: 8 Hours
Lugar de comienzo: Basilica Cateriniana San Domenico, Piazza S. Domenico, 1, 53100 Siena SI, Italy

Cancelaciones y devoluciones: For a full refund, cancel at least 24 hours in advance of the start time of the experience.


  • Driver/Guide
  • Transport by air-conditioned minivan (maximum 8 passengers)
  • Cheese tasting
  • Lunch
  • Alcoholic Beverages

No Incluye

  • Hotel pickup and drop-off
  • Gratuities


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