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Small-Group Montepulciano and Pienza Day Trip from Siena

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Siena, Italy
Small-Group Montepulciano and Pienza Day Trip from Siena
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Safety measures
icon8 hours  (approx.)
Mobile ticket
iconOffered in: English
Good for avoiding crowds

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Overview

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

9:30 AM
This activity will end right where it started.
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.
Itinerary
Pass By:  
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.
Stop At:  
Chiusure
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
Admission Ticket Free
Stop At:  
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.
Duration: 1 hour 
Admission Ticket Free
Stop At:  
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.
Duration: 15 minutes
Admission Ticket Free
Stop At:  
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.
Duration: 1 hour 
Admission Ticket Free
Stop At:  
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.
Duration: 1 hour 
Admission Ticket Free
Stop At:  
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.
Duration: 30 minutes
Admission Ticket Free
  • 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
  • OPERATED BY Tuscan Escapes by Papilio SRL
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.

Learn more about cancellations.


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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." See review

Reviews by Viator travelers.  We perform checks on reviews

Reviews

5.0
star-5
92 Reviews

Reviews by Viator travelers

We perform checks on reviews

Showing 1-10 of 92 reviews
star-4
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.
star-5
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.
star-5
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.
1 traveler found this review helpful
star-5
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!
star-5
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.
1 traveler found this review helpful
star-5
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.
star-5
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!
1 traveler found this review helpful
star-5
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.
star-5
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!
star-4
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.
star-5
Fantastic trip around Tuscany!
nmrugel
, Aug 2019
Ambra was a terrific guide — informative and fun! We enjoyed every stop — especially lunch on the farm!
1 traveler found this review helpful
star-5
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!
star-5
A combination of sightseeing and wine...
Tat A
, Jan 2018
A combination of sightseeing and wine tasting. Loved it.
star-1
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.
star-5
Wow - if I could give more stars, I...
Dabay
, Oct 2017
Wow - if I could give more stars, I would! This was definitely the highlight of our trip to Italy across Rome, Venice, Florence, and Siena. Corrado was an amazing guide, and took us through the rolling countryside of southern Tuscany, to small towns I'd only dreamed of. The views were breathtaking, and the farm lunch was so perfectly quaint and yet awe-inspiring the views were unreal! Visiting Pienza and Montepulciano was my dream come true, and I wish I could have spent more time in both beautiful towns. I can honestly say this was one of the top 5 days in my life - it was a once-in-a-lifetime experience, and the tour company took all of the guesswork out of the equation so we could truly relax and enjoy. I cannot recommend this tour enough.
star-5
What a fantastic day. Would highly...
Vickie C
, Oct 2017
What a fantastic day. Would highly recommend as the small group makes it so nice and personal. We had a great day seeing all the beautiful scenery and a WONDERFUL farm to table lunch in a fantastic spot. Nice to have a bit of free time to shop and walk Pienza as well.
star-5
Beautiful tour and very friendly...
Bill_S
, Oct 2017
Beautiful tour and very friendly guide. 2 very special places you must see and the countryside drive is very pleasant.
star-3
We had a wonderful guide - Elena...
Cynthia J
, Jul 2017
We had a wonderful guide - Elena - who was fun, friendly, considerate and very knowledgeable. She was an excellent driver. But we did feel that this tour was over priced. The midday farm meal was not generous and we had to wait for a long time to be served at each course. By comparison with other tables, our portions were smaller, including the wine. We assume that this was down to the sum paid by the company to the restaurant. Bear in mind, too, that although the guide gives you the history of both towns, it is not a guided tour as such and you are left on your own to explore. It would have been better value for money if the 2 towns were guided and then some time left free in each. There is, however, a very short guided tour of a Wine Cellar in Montepulciano and the option to taste. We were lucky enough to be the only people on this small-group tour but it would have been even less value for money if the group had been full. As I said, this is not a reflection on Elena because she was one of the best guides we have ever had.
star-5
Elena was such a great tour guide...
Shiree R
, May 2017
Elena was such a great tour guide. Our pickup was easy, the tour was informative and very interesting in all 3 locations. We stopped in an enchanting small village on the way to Pienza, it was gorgeous. There was enough time to walk about on our own in both Pienza and Montepulciano. The farm to table restaurant we had lunch at was absolutely stunning. I thoroughly recommend this tour to anyone.
star-5
Loved this tour, our tour guide...
Courtney_B
, Apr 2017
Loved this tour, our tour guide Elena was awesome, She was fun, knowledgeable and helpful. We loved the tour of the Tuscan countryside, what gorgeous, picturesque landscapes. We really enjoyed the town of Pienza, the whole town smells of cheese!!! In a good way : After Pienza, we went to an organic farm that made everything we ate and drank, it was delicious! We then went to Montelpulciano for a wine cave tour and a wine tasting. The wine was fantastic, so happy we ordered some! the whole day was lovely!

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