Small-Group Montepulciano and Pienza Day Trip from Siena

based on 176 reviews

Duration:8 hours (approx.)
Location: Siena, Tuscany

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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.

WHAT'S INCLUDED

WHAT TO EXPECT

1. Basilica Cateriniana Di S. Domenico
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.
2.
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.
3. Historic Centre of the City of Pienza
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.
4. Il Duomo di Pienza
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.
5. Val d'Orcia
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.
6. Montepulciano
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.
7. Piazza Grande a Montepulciano
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.

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Posted By : Ryan_B
- Exploring the small towns was cool
- Marco was top
- the farm was really nice
- the wine tasting was just ok
- the views trough the day were phenomenal
Rating : full ratings
Posted On : 2024-06-25 07:48:28

Posted By : Cathy_B
Juliana is Wonderful! Her easy going knowledgeable manner was so appreciated! The trip was so well planned, loved the capachino stop and farm lunch looking over the Tuscany views! I plan to come back next Fall and book this tour again!
Rating : full ratings
Posted On : 2024-06-21 12:23:50

Posted By : Julie_H
Great group and guide. Very fun day not to mention good wine. Tuscany is beautiful and all our stops were nice places
Rating : full ratings
Posted On : 2024-06-21 04:30:27

Posted By : Lare_Z
This was an amazing trip because our guide Giorgia was great, so knowledgeable and gave wonderful history lessons of the regions as well as wine making . Views beautiful and the hosts for lunch and wine tasting friendly and welcoming . Highly recommend!
Rating : full ratings
Posted On : 2024-06-21 03:32:18

Posted By : Laurie_S
This was a wonderful trip into the Val D'Orcia countryside. The Tuscan landscapes and the towns of Pienza and Montepulciano were terrific. Our guide, Marco, was awesome - full of information, humorous and wonderful to be with. Our small group of 6 enjoyed each other's company, too!
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Posted On : 2024-06-18 07:42:49

Posted By : Helen_M
A fantastic trip with Guillame (Bill) the guide entertaining and informative from start to finish. The small group was great to keep it fun and informal. The stops in little villages and viewpoints were great and lunch was fantastic. Worth every penny! Beautiful Tuscany at its finest!
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Posted On : 2024-06-16 16:01:22

Posted By : Shirley_R
We had the best day trip ever. Thank you to Marco for a fun day trip,very helpful with tips and informative. The day trip around Tuscany was beautiful and all the towns included in the tour were hidden gems with less tourists. The farm tour,wine and lunch was fantastic. Would highly recommend to any tourists looking to explore more of Tuscany from Siena.
Marco was also very helpful when we faced a train strike the day after and tried to help us get to Cinque Terre. He has gone above and beyond, and we were very grateful.
Rating : full ratings
Posted On : 2024-06-16 07:33:29

Posted By : whizzyPerth
Hello Giovanni - thank you for taking care of us on our tour of the Tuscan countryside and local towns of Pienza and Montepulciano. We also enjoyed the little coffee stop in Chiusure where we chatted with other visitors who were enjoying the break in the sun. You were charming and responded to all our questions, even the architectural ones! We loved the lunch at the organic farm and wine tasting. My birthday was memorable because the tour was well planned and not too overwhelming. Thank you again and stay well!
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Posted On : 2024-06-16 07:13:31

Posted By : Tricia_D
Exceptional time from beginning to end!! Our guide, Guillermo was amazing!!! A day full of visiting beautiful and charming towns with an incredible lunch at a Tuscan family farm with exceptional food, staff and views. Definitely a highlight of our trip.
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Posted On : 2024-06-14 03:38:27

Posted By : Kate_F
We had the most wonderful day tour with Juliana, she was so knowledgeable and interesting and kind. Gorgeous day with the most delicious organic lunch at the farm, view stops, and village locations to wander around and explore. Thank you so much it was a highlight of our trip to Tuscany 🇮🇹❤️
Rating : full ratings
Posted On : 2024-06-12 03:14:47