From Siena: Pienza and Montepulciano Wine Tour

Badge of ExcellenceSiena, Italy

From $93.07

Select Date and Travelers

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


Taste your way through Tuscany with this full-day wine tour of Montalcino, Pienza, and Montepulciano from Siena. Visit the charming town of Pienza and stop for one wine tasting each in Montepulciano and Montalcino.
  • Full-day wine tour of Montalcino, Pienza, and Montepulciano from Siena
  • Visit wine cellars and sample local wines in both Montalcino and Montepulciano
  • Enjoy free time to wander through Montalcino after the wine tasting
  • Explore the UNESCO-listed hilltop town of Pienza

What's Included

  • Travel by GT coach or minivan with air-conditioning
  • Expert multilingual escorts
  • Brunello di Montalcino Wine tasting
  • Self-guided visit of Montepulciano and Pienza
  • Gratuities
  • Hotel pickup and drop-off
  • Lunch

Meeting And Pickup

Meeting point

  • Bar Pedrocchino
    Viale Vittorio Veneto, 27, 53100 Siena SI, Italy

    Meet our staff in front of Bar Pedrocchino - Viale Vittorio Veneto 27

Start time

09:45 AM

End point

This activity ends back at the meeting point.

What To Expect

Meet your guide in Siena's Piazza Gramsci to begin the trip into the Tuscan hills.

Travel first to the pretty town of Montalcino, where you'll visit a wine cellar and sample some of the winery's vintages. Enjoy a delicious snack of local food products. After the first wine tasting, enjoy some free time to explore Montalcino.

Head next to the hilltop town of Pienza, one of the gems of the UNSECO-listed Val d'Orcia. Learn about pecorino, the local cheese made here. Stroll through the charming streets of this planned Renaissance town.

Continue to Montepulciano, the final stop of the day, for a visit to a local winery where you'll sample this area's famous Nobile di Montepulciano wine.

Return to the original departure point in Siena at the end of the day.

Strada Provinciale 71

Brunello wine tasting in a local winery

1 hour Admission Ticket Included

Chiesa della Madonna del Soccorso

During your free time visit this beautiful Church located on a panoramic spot

10 minutesAdmission Ticket Not Included

Additional Info

  • Confirmation will be received at time of booking
  • Customers must be able to climb and descend stairs. Please note that a moderate amount of walking is involved and this tour is not wheelchair accessible.
  • Portuguese language: Available on selected days and will be guaranteed with minimum 4 pax, if the minimum is not met the tour will be done in English or Spanish.
  • Not wheelchair accessible
  • Stroller accessible
  • Near public transportation
  • Infants must sit on laps
  • Infant seats available
  • Optional Lunch: please contact us if you wish to join us for lunch, or call
  • Most travelers can participate
  • This tour/activity will have a maximum of 50 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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55 reviews
Total review count and overall rating based on Viator and Tripadvisor reviews
Reviews by Viator travelers.
Showing 1-10 of 55 reviews
Fernanda_B, Nov 2022
The tour was just incredible, the guide was polite, knowledgeable and friendly. The wine was divine highly recommended!
Pienza is a Gem!!💎
Vanessa_N, Oct 2022
Wonderful tour!! Pienza is well worth a visit and is my favorite Medieval town. It has a great balance of history, restaurants, and shopping. I highly recommend!!
Nice tour
Steven_C, Oct 2022
Wine tasting, tour guide were all excellent. Thats all I have to say about this tour. We had a small group of 7 which worked out well.
Beautiful Tuscan fall day.
Michael_G, Oct 2022
Anna and our driver were fantastic. Lots of history. Winery was awesome. Would have liked more time in Montepulciano and less in Pienza. Pienza is small and not so much time is needed there.
Lovely visit to two villages and wine tasting
Alison_M, Oct 2022
Wonderful day trip into the Tuscan countryside. Visited two stunning villages and great wine tasting at a gorgeous winery on the way back to Siena. Would highly recommend.
The winery visit was a...
Steve_S, Oct 2022
The winery visit was a waste of time . Julia was good. Driver should play less music and give us quiet Julia our guide was good
Skip this if you cannot easily do lots of steep steps.
Cecelia_K, Oct 2022
The abundance of steep steps that we had to climb; the reviews and description of the tour did not say anything about the steps: we had difficulty climbing them and even skipped the last stop during the tour because of the steps. Very disappointing.
Enjoyable day tour
hjgc429bhj, Oct 2022
We really enjoyed our tour with Anna to the winery, Pienza and Montepulciano. The amount of free time to explore the towns was appreciated. The tour bus was comfortable and clean, and the driver was excellent. Anna was informative and friendly and her English was good. We learned new things about Brunello wines at the winery. It was a very pleasant day and we’re glad we took the tour.
If you can, just rent a car and go to the places yourself
Maria_A, Aug 2022
I was very underwhelmed with the experience. While I liked the winery and tasting, I had expected to be taken to the field to see the vines and get a thorough explanation of the process. I think the ad is misleading making you think that you will also visit a winery in Montepulciano, which you don't unless you organize it yourself. Other than the winery, the tour just consists on dropping you off in the other towns, which are lovely, but you can just do it yourself
Response from Host, Aug 2022
Dear Maria Greetings from my Tour in Italy team First of all you have free time in the city don’t include guided visit. During the time in the bus the guide explain the city , the history and the highlights. And this tour include wine tasting at one of the best wineries of the region. Best regards
Wine trip
Gerwin_B, Jul 2022
Good gide and chauffeur. Luciano and Marciano! Friendly and helpfull. Very nice trip. Good wine tasting.
Fabulous experience
Carolyn_C, Jun 2022
A brilliant experience. Stunning views. Wine tasting was so well organised and a lovely experience. Would totally recommend this trip. A really enjoyable day.
Response from Host, Jul 2022
Dear Carolyn, We appreciate you for choosing us and taking this tour with us. It is so nice to know that our team helped you to have a wonderful journey. Will be our pleasure to have you back again in the future. Best Regards My Tour
Super enjoyable tour
Giampaolo_P, Jun 2022
The tour was very pleasant overall. The minivan departed on time (10am) from the meeting point and it was 7 of us in total. First stop was the wine tasting at a local farm/winery, which included 4 glasses of wine, a shot of grappa and some cured meats, cheese with bread and olive oil. We then had free time in both Pienza (about 1 hour) and Montepulciano (about 2 hours) to explore the cities. From both places the views over the Val d’Orcia are breathtaking. The driver and guide, Vincenzo in our case, was very knowledgeable, friendly and fluent in Italian, English and Spanish. I would definitely recommend this tour if you want a taste of the beautiful Val d’Orcia and its wines.
Response from Host, Jun 2022
Dear Giampaolo, Thank you so much for sharing your experience with My Tour. Our goal is 100% customer satisfaction and it sounds like we achieved that goal with you. Looking forward to have you back again in the future. Best Regards My Tour
Worth it
MICHAEL_W, May 2022
The guide was very friendly, but personal hygiene was an issue. The tour was comprehensive, but the guide read from cue cards. It would have been nice to see the actual grapes vines. The cellar in Montepulciano was amazing. The guide took us to an incredible view of the Tuscan countryside as a bonus.
Response from Host, May 2022
Dear customer, thank you for your feedback, we are so sorry about the issue you pointed out. We will do our best to check it and improve it! We hope you enjoyed the experience! Thank you for choosing us, hope to see you again on another tour all around Italy!
Amazing !
Tanner_D, May 2022
Breathtaking views, a cool winery, and super charming little towns. Vincenzo was a great guide and because it was only 8 we took a van instead of a bus which was very enjoyable. Would recommend for anyone who wants to see the amazing Tuscan countryside.
Response from Host, May 2022
Dear Tanner, thank you for your positive feedback. We appreciate it and we're glad to hear from you that you spent such a lovely time with our team in Val d'Orcia. Hope to see you again on another tour all around Italy!
Medieval to Renaissance wine experience
Dean_S, May 2022
Luca was a great guide, patient and knowledgeable. The areas we went were amazing the wines equally so. It was a fun group of people.
Response from Host, May 2022
Dear Dean, thank you for your positive review, we're glad to hear that you spent such a beautiful day with one of our best tour leaders! Thank you, hope to see you again on another tour with us all around Italy!
I loved the detail to the...
Jenny_C, Apr 2022
I loved the detail to the information. It was a very unique experience, a great exhibition showing you the beauty of time and nature.
Response from Host, Apr 2022
Dear Jenny, thank you for your feedback. We're glad to hear from you that you spent such a lovely time with our staff. Thank you, hope to see you again on another experience all around Italy!
Great valdorcia experience
Louis_T, Nov 2021
Was great! Had an awesome trip with my bestie!! Guide was very friendly and patient. Drove us to the scenic spots
Response from Host, Dec 2021
Dear Louis, thank you for your feedback, we're glad to hear from you that you enjoyed this amazing tour with us. We hope to see you again all around Italy!
We had a great day in Val d'Orcia...
Patrizia T, Mar 2018
We had a great day in Val d'Orcia. Our trip started from Siena, a car driven by a kind man brought us to a meeting point along the road to Montepulciano, where we got onto a van from Florence, with the guide and other tourists. The three places are wonderful, we saw stunning landscapes and tested different kinds of excellent wines inside two ancient canteens, They also offered us cheese, salame, bread.The only negative aspect was the weather, foggy and rainy, but it was not their fault!!
A tour from hell. Meet near Siena...
elisha R, Nov 2017
A tour from hell. Meet near Siena wall. Going to get guide and start from there. Yeah, and too many other people are then walked about 1/2 mile to a bus that we boarded. Only to be taken many miles outside city to travel plaza where we were grouped with another group who had came from Florence onto a double decker bus--ugh. They were off using bathrooms as we were told to board and find any available seats. problem? there were single seats here and there and we were a traveling party of 4. we had to wait for two passengers and started to the villages way later... the group is way too large --wineries couldn't handle us and we were broken into two groups and still crowded way thru wineries. the area is beautiful , great little towns but descriptions don't tell the honest truth about the cattle call that this tour truly is. don't do this tour!
What was an OK trip could have been...
Renae D. L, Oct 2017
What was an OK trip could have been a great trip if there hadn't been so much wasted time. The 3 towns we visited were worth seeing and the Montalcino wine tasting was fun, with Mario the passionate winery owner proudly showing off his wines. Pienza was small and I could have missed that in exchange for more time in one of the other two towns. Our issue was with all the wasted time. We were asked to arrive at 9am for a 9:15am tour start, but at 9:15am, there was no tour guide there. A gentleman showed up to meet us and walk us to the bus. We boarded the bus well after 9:30 and drove to a mini-mart/gas station on the highway, where were we told we were waiting for the tour guide who would arrive in 5-10 minutes. When the tour guide and another bus of people arrived 45 minutes later, that group was allowed to get off the bus to use the restrooms. By the time both groups were ready and our group had boarded the second bus, it was close to 11am. So the 9am start was now 11am and the 6-7pm conclusion of the tour turned out to be almost 8:30pm. All in all, nice towns but a lot of wasted time and miscommunication. We had a similar experience with a Viator tour in Greece, so I think we are done with Viator.