Small-Group Montepulciano and Pienza Day Trip from Siena

Badge of ExcellenceSiena, Italy

From $176.09

Select Date and Travelers

Free cancellation
Up to 24 hours in advance.
  • 8 hours (approx.)
  • Mobile ticket
  • Offered in: English


Discover Tuscany's stunning landscape, culinary delights and UNESCO-listed sites on a day trip to Montepulciano and Pienza from Siena. Led by a local guide, admire the architectural gems of the Val d'Orcia region and stop at a dairy farm for lunch and samples of salty Pecorino cheese. Conclude your trip in the scenic hill town of Montepulciano, with an optional visit to a winery. Group size is limited to eight people, ensuring personalized attention from your guide.
  • Guided full-day trip to Montepulciano and Pienza from Siena
  • Discover the Val d'Orcia, a UNESCO World Heritage Site
  • Savor lunch and a Pecorino cheese tasting (included) on an organic dairy farm with spectacular views
  • Small-group tour with a maximum of eight people ensures an intimate experience

What's Included

  • Driver/Guide
  • Transport by air-conditioned minivan (maximum 8 passengers)
  • Cheese tasting
  • Lunch
  • Alcoholic Beverages
  • Hotel pickup and drop-off
  • Gratuities

Meeting And Pickup

Meeting point

  • Basilica Cateriniana San Domenico
    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.

Start time

09:30 AM

End point

This activity ends back at the meeting point.

What To Expect

Begin your day trip with pickup in Siena, where you’ll hop aboard your minivan and travel toward Pienza with your guide. Pass through the Crete Senesi along the way, clay hills with a lunar-like appearance as a result of the soil’s gray coloring. 

Arrive in the town of Pienza, the gem of the UNESCO-listed Val d’Orcia region. Enjoy some free time to explore here independently, strolling the streets or perusing the local shops.

Head next to a dairy farm for a delicious lunch made from the farm's fresh ingredients. Treat your taste buds to a sampling of salty Pecorino cheese, a favorite in Italy, and hear about the farm’s history and production process.

Continue to Montepulciano, a hill town overlooking the scenic Tuscany-Umbria border. Take a guided stroll around the Piazza Grande before wandering the churches, palaces or stores at your leisure. On request, make an additional stop at a winery for a tour of the cellars and tastes of Montepulciano’s celebrated vino.

After a full day of fine food and exploration, your tour will conclude with transportation back to Siena.

Basilica Cateriniana Di S. Domenico (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.


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 minutesAdmission Ticket Free

Additional Info

  • 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
  • No heart problems or other serious medical conditions
  • Most travelers can participate
  • This tour/activity will have a maximum of 8 travelers

Cancellation Policy

You can cancel up to 24 hours in advance of the experience for a full refund.

  • For a full refund, you must cancel at least 24 hours before the experience’s start 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.

Traveler Photos

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Traveler Tips

Small tours allow more conversation among the group, more opportunity to ask the guide questions, and the small vans can drop you off close to the walled towns and quickly maneuver through traffic better than giant tour busses.
104 reviews
Total review count and overall rating based on Viator and Tripadvisor reviews
Reviews by Viator travelers.
Showing 1-10 of 104 reviews
Wonderful and memorable experience!
Anna_S, Mar 2023
Excellent tour! we loved our tour guide Elio - informative and very funny. He showed us wonderful places. We loved the lunch with a wine making family!! Such a memorable experience! Thank you Elio!
Great, well worth it
JeanYves_R, Oct 2022
Guide was very helpful. Visited the countryside, small village, great vistas, lovely outdoor lunch with more views and wine. Pienza and Motepulciano are beautiful historic towns. Wine tasting was great. Perfect day
Amazing Tour
BARRY_S, Oct 2022
The whole day was thoroughly enjoyable. Guillermo was terrific..knowledgeable and fun. Great stops with enough free time to explore. Loved Pienza, the farm and Montepulciano. Highly recommended.
Postcard views
Dawn_H, Oct 2022
We had a perfect day with our tour guide, Ambra! She showed took us to all sorts of interesting places and views! This was a perfect way to see the rolling Tuscan hills and countryside without the worry of renting a car. We first stopped for coffee at a tiny town, to break up the drive. Then had pecorino cheese tasting at a farm outside of Piensa and a wonderful zucchini spelt dish for lunch. Piensa was definitely our favorite Tuscan town, postcard views everywhere you looked! Highly recommend the tour!
A piece of heaven on earth
VIDUR_K, Sep 2022
The rolling hills of Tuscany.. idyllic little towns. Great food! A terrific guide and driver in Georgia. Tuscan Escapes is a fabulous option for this magnificent tour of a piece of heaven on earth.
Thomas_H, Sep 2022
The guide was very knowledgeable. The views were amazing, and the towns were lovely. The lunch with cheese tasting was delicious!
Lazy day in the countryside
Rosalie_A, Aug 2022
Lovely trip thru the countryside with our guide Daniele, including a stop for a light lunch at a family run agriturismo farm. There were only 3 participants on the tour (myself, my 20 y.o. daughter and another gentleman) making this a more intimate experience and we were able to customize the itinerary a bit. Nobody was interested in visiting a wine cellar which allowed for more time to explore Montepulciano. The towns we visited were small and quaint, thus keeping the day quite laid back. I would not recommend this tour for individuals seeking a fast paced and lively excursion nor families with children requiring constant entertainment.
Excellent guide, Ambra,...
Judith_R, Jul 2022
Excellent guide, Ambra, was entertaining and well-informed. This is a well-managed tour operator. A delightful experience.
Wonderful Day
Matthew_G, May 2022
We had a wonderful day in May 2022 with Marella on this tour. She showed us all sorts of interesting places and views. We booked this instead of renting a car, and we were glad we made that decision. Marella was a lot of fun to spend the day with, she took us to places we would not have selected on our own, and we didn't have to deal with directions and a designated driver. Some of the highlights were the tiny village where we first stopped for coffee, the great lunch, and Piensa. The winery in Montepulciano was interesting because the caves were so old (from the Etruscan era), but the wine itself was just so so and the place was uncomfortably crowded. All in all, this "small-group" tour, which turned out to just be the two of us, was one of the best days on our Italy trip.
Wonderful tour!
Zubaoyi_Y, Dec 2021
This was our 1/3 trips led by Georgia. She was so attentive and Knowledgeable as a tour guide, and incredibly charming as a person. Tours of Montepulciano and Pienza were mostly self-led, but it worked out well because she took us to the most important sites and told us about the history of the towns and what to look for during the car ride there. We had a lot of fun and 100% recommend this tour!
Highly recommend
Tayllor_L, Jul 2021
Incredible day trip! We couldn’t have had a better guide, the views were phenomenal and the lunch was even better than expected.
Rolling Tuscan Hill views and beautiful old towns to wander
Jennifer_S, Apr 2020
What an extraordinary day from start to finish. Our group had a lovely drive through the hills stopping in a little town for coffee. Both Pienza and Montepulciano are beautiful each in their own way. We had enough time to walk around and see the main streets and a few little side alleys. Every few feet was a postcard view. Incredible. The included lunch was very good and after we had a quick visit with some of the animals on the property. Our guide was terrific and gave us a lot of information along the drive and as we arrived in each town. The whole tour process works well. The meet up at the church went quickly and we were dropped off there at the end of the day. I purposely chose a hotel a 2 minutes walk from the meeting point since my three full days in Sienna included two days on these small group tours with this company. Overall I thinks it's very good value for the money. Small tours allow more conversation among the group, more opportunity to ask the guide questions, and the small vans can drop you off close to the walled towns and quickly maneuver through traffic better than giant tour busses.
Small group to Montepulciano and Pienza Day trip
Rhonda_B, Dec 2019
Our guide Georgia was Amazing! She was so knowledgeable and very interesting to listen to. The trip left from Siena. The views of the Tuscan area was Outstanding, the farm to table lunch was the best part of the trip. Would do this trip again!
An easy way to see the countryside
Kathleen_T, Nov 2019
We had a lovely day with our tour guide, Ambra! I could have skipped the stop for tea/coffee in Asciano so that we could have more time in Pienza and Montepulciano, but we knew when we booked the trip that our time there would be limited. We enjoyed lunch on the patio at the pecorino farm. The view was absolutely beautiful! Lunch was light but good (but no meat). I was surprised that the pasta was a cold rotini salad from pre-made pasta---not the fresh pasta you'd expect in Italy. Ambra made the trip special. We stopped in several places so she could take photos of us. She is passionate about Italian history and culture and we really enjoyed talking to her. We took another Tuscan Escapes trip the next day and also had a good experience. I think their trips are a good way to see the countryside and explore hill towns if you don't have a car and don't want to deal with public transportation.
Day trip to Pienza and Montepluciano
Steven_T, Oct 2019
We had a lovely day trip from Siena to Pienza and Montepluciano with TuscanEscapes Tours. The eight hour tour included an unbelievable lunch stop at Podore I’ll Casale along with a nice visit to Pienza and Montepluciano. Our guide was very cool and fun to be with as well as very knowledgeable. Lastly, we had a fun wine tasting De’Ricci in Montepluciano and was able to learn a lot about the historic building and wine making family. A wonderful day!
Tour guide
margie_s, Oct 2019
Tour guide should have known that the bathroom was near the bus instead of sending me all the way back up the main street.
Fantastic trip around Tuscany!
nmrugel, Aug 2019
Ambra was a terrific guide — informative and fun! We enjoyed every stop — especially lunch on the farm!
Excellent, highly recommend!
Darlene M, Jun 2018
The trip was amazing! Pienza is a beautiful town! Our tour guide Elena was excellent, so knowledgeable and so nice. The lunch destination was almost heaven! Delicious food and the best views in all of Tuscany! I highly recommend this tour you will not be disappointed!
A combination of sightseeing and wine...
Tat A, Jan 2018
A combination of sightseeing and wine tasting. Loved it.
Beautiful views, delightful lunch...
Angela L, Dec 2017
Beautiful views, delightful lunch, good guide. A small van tour is much p Beautiful countryside, good guide, small group as opposed to a big bus, delightful lunch and who would not fall in love with Pienza and Montepulciano.