Small-Group Montepulciano and Pienza Day Trip from Siena

Siena, Italy
Small Group Montepulciano and Pienza Day Trip from Siena
  • 8 hours
  • 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)
  • 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)


30 minutesAdmission Ticket Free

Historic Centre of the City of Pienza

1 hour Admission Ticket Free

Il Duomo di Pienza

15 minutesAdmission Ticket Free

Val d'Orcia

1 hour Admission Ticket Free


1 hour Admission Ticket Free

Piazza Grande a Montepulciano

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

See more
Featured review
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!


145 reviews
Total review count and overall rating based on Viator and Tripadvisor reviews
Reviews by Viator travelers.
Showing 1-10 of 145 reviews
Randall_P, Nov 2023
Our family LOVED this tour!! The towns we stopped at were amazing! Lunch was great and the winery was wonderful. Most of all, Elio was the best tour guide ever! Thanks, Elio for making the tour more fun than we could have imagined and a great memory of our first trip to Italy! I can speak for the whole family when I say I would definitely recommend this tour!!
A great, relaxing way to see Tuscany. Worth every penny.
Ann_H, Oct 2023
We considered renting a car for the day, but glad we took the tour instead. Able to visit 3 hilltowns, learn the history of the area and enjoy a fantastic lunch. This was true lt a small group experience with an interesting group of people. Julianna, our guide, was well informed and fun.
Our tour to Pienza, Montepulciano
Kathy_L, Oct 2023
We had the best experience EVER with Emilio?? martini- 3 couples who all connected, very informative English speaking guide. We visited beautiful villages, stopped for coffee at a sweet couple’s place, fabulous lunch at farm and a wine tasting. The day was perfect in every way!
Great day out of Siena to experience all Tuscany has to offer
Julie_P, Oct 2023
Guillermo was a fun and entertaining guide. Very accommodating. Ended up with a group of women who were doing a girls trip together and ended up friends at the end of the trip! Italian countryside was gorgeous and the cities were straight off of a movie set! So much charm! Would have loved to your the farm a bit more.
Highly recommend
FRANCE_L, Sep 2023
Very well organized and Guillermo was fantastico! He was friendly and funny and made the day so much fun. He knows is stuff.
Lunch in Pienza was...
Rosalind_L, Sep 2023
Lunch in Pienza was wonderful and the food was delicious. We also loved walking through the towns and churches.
Amazing experience! I would take this tour again when I return to Italy
Melissa_L, Sep 2023
This tour was amazing! Everything about it was great, starting with how easy it was to find the pick up spot for the tour. The tour guide was the best! He was funny, informative, and kind. It was raining when our tour was ending and he dropped me off at my hotel so I wouldn't have to walk back in the rain. The food was one of the best meals I had while in Italy. It was farm to table fresh and delicious! I would 100% take this tour again and would recommend it to anyone! My only wish was an extra 1/2 in the towns. The hour I had was enough to get a taste of the town, but a little extra time would have allowed for some shopping and/or a glass of wine or Gelato.
Top notch tour
Ty_T, Aug 2023
Absolutely great tour! Our guide, Giuliana, was so much fun and knew so much about the area. Consider yourself lucky if you get her as a guide! The lunch at the agriturismo was outstanding with everything being produced right on the farm. The little Tuscan hill towns were so quaint and the countryside was beautiful! We did not feel rushed for town at any of the places we visited!
A lovely tour of the Tuscan countryside.
George_J, Jul 2023
We had an amazing and fun trip. Our tour guide Guglielmo (or William in English) was a fabulous guide. He was friendly, gracious, and incredibly knowledgeable about the region, both today as well as the history since the Estrucans. Guglielmo was a humorous, and wonderful story teller. We were a bit concerned, that the trip might be rushed in order to finish in a certain allotment of time. However, that was not the case. Guglielmo was very patient and let us determine how much time we spent in any particular location. The van we travelled in was newer, and very comfortable, and well air conditioned. Guglielmo was an excellent and smooth driver. We visited a number of both small and larger villages in Tuscany. It was a lovely mix of activities, spectacular vistas, and interactions with locals. Nearly every scene you observe is fabulous. We started in a very small and quaint village were we stopped for a morning cappuccino at a delightful little shop. We ate lunch that included a wine and cheese tasting, at a a dairy, with its own amazing views. We also stopped in a small winery, and had another tasting there. Our visit included a tour of their cellar. Guglielmo was an exceptional tour guide, and he really made the trip fun as well as fascinating. Both of us are teachers, and we can tell when someone loves working with people and sharing their knowledge, and that was Guglielmo's gift. Please thank Guglielmo for a memorable tour.
We had a wonderful day!...
Linda_S, Jul 2023
We had a wonderful day! Our driver was entertaining, friendly, and very knowledgeable. The towns are lovely and the food & wine was delicious.
Great Tour, Amazing Guide
Gabriel_G, Jul 2023
Guiliana was absolutely amazing! She was very knowledgeable and familiar with the region and the history. My partner and I had an amazing experience at all our destinations and the wine and food were fantastic! We especially were pleasantly surprised by Pienza. Such a cute village and the entire countryside was beautiful. We would highly recommend this trip.
Best guide Mattia.
Becky_h, Jun 2023
Mattia was great. Very personal with a lot of history to share. Best was lunch....minus the flies. Suggest water for passengers and small snack with first wine stop.
Fantastic Day
Todd_M, Jun 2023
Fantastic day in Tuscany. Highly recommended! My family would definitely do the tour again as every detail/experience was perfect. Thank u
Fantastic small group trip into the Tuscany countryside
Marianne_G, May 2023
We were picked up on time at the location outside the Basilica Cateriniana San Domenico in a very comfortable minivan with a total of 8 passengers for the day. Guglielmo (William) was our wonderful guide for the day. He was very informative, upbeat and a great driver on the winding roads. The tour was well paced with stops at viewpoints for the beautiful Tuscan countyside as well as visits to the towns of Pienza & Montepulciano. Lunch at the organic farm overlooking the Val d'Orcia was wonderful! We also had a wine tasting at Montepulciano. Highly recommend this tour with Tuscan Escapes.
Outstanding trip with an outstanding tour guide
James_C, May 2023
We enjoyed a wonderful full day trip to Montepulciano and Pienza with lovely travelling companions. Our tour guide Guglielmo was outstanding, and he made the trip so special. He was very welcoming and friendly, attentive, flexible and full of knowledge which he shared with everyone in the group. We also enjoyed the delicious cheese and wine tasting, and the lunch too. We will always remember this very special day. Thank you Guglielmo, Tuscan Escapes and Viator.
Great full day tour
Simone_G, Apr 2023
LOVED this trip, so great! But one of the things that makes it SO great is the tour guide Guilliame who took our tour - Brilliant! The best - smartest, most knowledgeable, funniest
Best Guide
Lisa_T, Apr 2023
Our guide William was amazing! We was funny and kept us entertained all day. He was so knowledgeable about the area and the history of the places we visited. I would highly recommended this tour but especially William as your tour guide. Hands down our best day in Italy!
Great tour!
Margaret_L, Apr 2023
Our guide, William, was the best! So enthusiastic, knowledgeable, and a good sense of humor. The countryside was beautiful and the farm lunch delicious and so very fresh. The wine tasting was and free time all worked out well.
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

From $199.11

up to 24 hours before the experience starts (local time)

Compare Similar Experiences

1 / 3
No Photo
Small-Group Montepulciano and Pienza Day Trip from Siena


8 hours
Free Cancellation
No Photo
Small-Group Chianti and San Gimignano Sunset Trip from Siena


8 to 9 hours
Free Cancellation
Likely to Sell Out
No Photo
From Siena: Pienza and Montepulciano Wine Tour


11 hours 30 minutes
Free Cancellation

Explore Similar Things to Do