Tours & activities by Travelsignposts Pty Ltd. from Viator

  • Location: Siena, Italy
  • Duration: 8 hours (approx.)
From USD $150.73

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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-listed landscapes of Tuscany's charming Val d’Orcia region. Explore the beautiful towns, enjoy lunch and taste Pecorino cheese on a local farm!

Numbers are limited to eight people on this small-group tour, ensuring you'll receive personalized attention from your guide.


  • Great overview and orientation of the city
  • Informative, friendly and professional guide
  • Perfect introduction for first-time visitors
Meet your friendly guide in central Siena and head out of town in a comfortable minivan on one of Tuscany's panoramic roads, passing through the characteristic clay hills known as the Crete Senesi. Arrive first in the beautiful town of Pienza, which was entirely planned out by Pope Pius II, the humanist pope, to be the ideal Renaissance town.

Pienza is rightly considered the gem of the Val d’Orcia region; the town and the entire Val d’Orcia are World Heritage Sites. You'll have time to spend at leisure here, so make the most of it by shopping or exploring the pretty alleyways of this small town at your leisure. As you leave Pienza, enjoy the fantastic views of Tuscany’s famous picture-perfect scenery.

Your next stop is a local dairy farm, where you’ll feast on a wholesome and refreshing lunch (included) of fresh ingredients mostly produced on the farm. You’ll also enjoy a tasting of Italy’s salty Pecorino cheese, hear about the cheese-making process, visit the farm’s animals and learn about the lifestyle of the area.

In the afternoon, travel to Montepulciano, one of Tuscany’s biggest hill towns, located on a steep hill overlooking the amazing landscape of the Tuscany-Umbria border. With your guide, take a short walk around town to see the Piazza Grande at the top of the hill. You’ll then have free time to visit the town’s many stores, palaces or churches. On request, visit a winery to enjoy a tasting of Montepulciano’s renowned wine and tour the wine cellars before your relaxing ride back to Siena.

Recent Photos of this Tour

Schedule details

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Departure Dates:
Departure Point:
San Domenico Basilica
Departure Time:
8 hours (approx.)
Return Details:
Returns to original departure point

Pricing information

Click the link below to check pricing & availability on your preferred travel date. Our pricing is constantly updated to ensure you always receive the lowest price possible.


Pricing information

Small-Group Montepulciano and Pienza Day Trip from Siena

Small-Group Montepulciano and Pienza Day Trip from Siena

  • Driver/Guide
  • Transport by air-conditioned minivan (maximum 8 passengers)
  • Cheese tasting
  • Lunch
  • Hotel pickup and drop-off
  • Gratuities (optional)
Additional Information:
  • Confirmation will be received at time of booking, unless booked within 1 day 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
Voucher Info
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Local Operator Information:
Complete Operator information, including local telephone numbers at your destination, are included on your Confirmation Voucher. Our Product Managers select only the most experienced and reliable operators in each destination, removing the guesswork for you, and ensuring your peace of mind.

Cancellation Policy

If you cancel at least 7 day(s) in advance of the scheduled departure, there is no cancellation fee.
If you cancel between 3 and 6 day(s) in advance of the scheduled departure, there is a 50 percent cancellation fee.
If you cancel within 2 day(s) of the scheduled departure, there is a 100 percent cancellation fee.

Traveler Reviews

Reviewed by: Lisa O, January 2017

Elena was a fantastic tour guide. Fortunately, my boyfriend and I were the only people on the tour that day so we got a lot of undivided attention. We definitely felt like we'd gotten the special treatment!
Elena met us, on time, at our designated pick-up spot and quickly whisked us off toward Pienza. We stopped at a little village along the way for a cup of coffee she refused to let us pay and a bit of sightseeing. From there we headed to a farm for lunch one of our favorite locations/experiences of our entire two weeks in Italy and then into Pienza proper. What a beautiful town! Elena walked us through the town, giving us great historic information, and then allowed us to wander leisurely for the rest of our time there.
On our way to Montepulciano, Elena was kind enough to pull over, allowing me to capture some of the breathtaking landscape with my camera. Once we arrived in Montepulciano she again walked with us to give us historical insight, but then gave us time to take in the town at our own pace.
Upon our return to Siena she was kind enough to drop us off closer to our apartment rather than the designated drop off point which was so appreciated after a long day of touring.
Do not miss these two towns when you're in Tuscany - and this Viator tour was the perfect way for us to experience them! We never felt rushed and we probably wouldn't have seen half of the wonderful sights we were shown had we driven there on our own.

Reviewed by: Judy G, January 2017

This is my second attempt to post a review. My husband and I are still raving about our wonderful tour with Sylvia in October. It was a fabulous day and one of the highlights of our entire trip. The tour was perfectly timed, beginning with a coffee stop in charming little Chiusure, anchored by an unforgettable meal at the biodynamic farm, and finishing just as the rain began in Montepulciano. Sylvia was a delightful host and the tour exceeded our expectations.