Tours/Siena/Small-Group Montepulciano and Pienza Day Trip from Siena
Viator · group up to 8 pax

Small-Group Montepulciano and Pienza Day Trip from Siena

4.9(319)Siena1 hour
VIATOR4.9(182)TRIPADVISOR5.0(137)

Description

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.

Tour Options

Small-Group Montepulciano and Pienza Day Trip from Siena

Itinerary

Pass by

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.

30 min

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.

60 min

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.

15 min

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.

60 min

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 min

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.

30 min

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.

Highlights

Transport by air-conditioned minivan (maximum 8 passengers)
Alcoholic Beverages
Lunch on local farm with wine
Driver/Guide

What's included

Included
Transport by air-conditioned minivan (maximum 8 passengers)
Alcoholic Beverages
Lunch on local farm with wine
Driver/Guide
Not included
Hotel pickup and drop-off
Gratuities

Traveller Ratings

4.9
319 reviews
5
299
4
14
3
2
2
3
1
1

Important Information

  • 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

Reviews(319)

C
christinekL9238LQ
August 4, 2026
Delightful

This was the highlight of our trip to Italy. Mattia was a wonderful driver with a depth of knowledge, as well as a warm, humorous disposition. The small group made it more enjoyable and was a great way to make friends. Our group even met up later for dinner! The towns and picturesque vistas were worth it alone, but the delicious lunch at the farm was very special. Overall: great food, great wine, great views, and great company.

H
hannahgY3445ZU
August 2, 2026
Amazing day tour

I had the best day visiting Pienza and Montepulciano, Georgia our guide was incredible. She had a wealth of knowledge about Tuscan history, wine, and just about everything. Lunch at the Farm was so gorgeous, and the wine tasting was great. Pienza has been my favourite small city to visit Tuscany. It’s peaceful and cute, definitely don’t skip it! Couldn’t recommend this tour enough!

L
Laura_O
July 23, 2026
A nice day out

I had a very nice day, I thought they gave us enough time to enjoy each activity and I liked that, I liked the places they took us to. I would only change the place where they gave us lunch, it is nice and they served us well, but the food could have been better.

T
toddg2225301
June 23, 2026
Fabulous day, great guide!

A fabulous day of touring, education, food, and wine. Our guide, Keko, was superb. The beautiful drive through the Val d'Orcia was made all the more memorable by the extensive history and cultural insights provided by Keko. We learned A LOT. Pienza was a pleasant stroll, but the highlight was Montepulciano if just for the views of Tuscany. Definitely a day well spent, made all the more memorable by having a fantastic guide. Well done, Keko!

R
Renata I
June 16, 2026
The Perfect Tour

It was a perfect day with our guide Giorgia. The chosen places were very beautiful, as was the food and the wines. Giorgia was very kind and also helped each member of the group who had different needs or desires. She told the history of Siena, Chiusure, Pienza, Montepulciano, and other villages in a very pleasant way, and it is clear that she knows everything very well.

7
703sheam
June 15, 2026
Unforgettable experience with Juliana!

I recently took the Pienza and Montepulciano Tour from Siena with Tuscan Escapes, and our guide, Juliana, made the entire day unforgettable. She was incredibly knowledgeable, warm, and passionate about the region, bringing the history and culture of both towns to life. Her local recommendations were absolutely spot on..Tip for future travelers: Be sure to bring cash with you for a tip! They do not have an online tipping system, and wonderful guides like Juliana truly deserve it. I highly recommend this tour, especially if you don’t have a car!

J
Jennifer_H
June 11, 2026
Our time in Montepulciano...

Our time in Montepulciano was one of our favorite days in Italy. Giovanni was an exceptional guide and he taught us so much about the wine and the area. We highly recommend Tuscan Wine Tours as they book small wineries. Our delicious lunch was at a dairy farm where we overlooked the gorgeous Tuscan region.

A
abigailaV9628HH
June 7, 2026
Amazing

Me and my mom enjoyed our tour in yeahand Pienza. It was a beautiful experience and the views were breathtaking.

L
lauratD9162QW
June 7, 2026
Fantastic day in Tuscany!

This was a great way to see Tuscany if you don’t have a car! I really loved the beautiful little towns we visited, driving through the countryside, and our guide Sandro who was the best. Lunch was tasty and the farmhouse we had it at was really cool. If you’d prefer to be in a small group, rather than a large tour, this one’s for you! We all got along really well, and there was ample time to explore by ourselves if we wanted to, too.

N
Nicola_R
June 6, 2026
Stunning Views

Had an excellent time exploring the countryside, beautiful views, plenty of food and good wine. Worth every cent.

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