Available languages
10 hours 30 minutes
Mobile ticket
DEPARTURE GUARANTEED!
Enjoy a perfect day trip visiting 3 of the most impressive places in Tuscany. Montalcino, house of "Brunello" wine; Pienza, well known for the "Pecorino" cheese and Montepulciano where the undisputed symbol is the "Nobile di Montepulciano" wine!
Please note that from November to April we cannot guarantee the restaurant with view, as stated in the inclusions.
The Valdorcia has been recognized as UNESCO world heritage site since 2004, as it was an inspiration for many Renaissance painters.
There you will be surrounded by impressive views, art, culture, amazing wine and delicious food!
Our semi private tour will be on board of a premium minivan with an english speaking driver, air conditioning and free water.
WHY CHOOSE US?
Secure bookings, Guaranted Departures!
48 hours Cancellation policy, best rates guaranteed!
Group of maximum 8 people.
Infants and small children can ride in a pram or stroller
Public transportation options are available nearby
Specialized infant seats are available
Suitable for all physical fitness levels
For a full refund, cancel at least 24 hours before the scheduled departure time.
Florence
08:00AM: Meet our English speaking driver and let's the tour begin!
Montalcino
09:45AM: The first stop will be in a great winery in Montalcino... The winery is owned by a local family and, talking with them, you will not have the feeling to visit their work place but their home instead!...You will know everything about Brunello di Montalcino: the vineyard techniques , the wine making process, its ageing and ,off course, how to appreciate it by drinking different vintages!
2 Wine Tastings
Local product food tasting during the wine tasting in Montepulciano
Guided tour on vineyard and barrel cellar
Premium van with A/C
Superior Lunch with stunning view (November to April we cannot guarantee the restaurant with view)
English-speaking driver (driver is not the guide)
Guided tour on the underground city of Montepulciano
Gratuities
Private Pick-Up
367 reviews
Total reviews and rating from Viator & Tripadvisor
Frank A,Apr 3, 2026
- Review from Viator
This tour to Montalcino and Montepulciano, and the respective wine tasting experiences was exceptional. In Montalcino we visited a small family owned and operated winery which produces superlative Brunello wines. We tasted 4 Brunello’s, a Rosso a Rose and an IGT blend. Each of these wines was unique and delicious. I bought a mixed case! Lunch in Pienza at a small Trattoria was a refreshing respite between our tasting experiences. In Montepulciano we visited a subterranean winery dating back to the medieval and early renaissance periods, with one section dug in 400 BCE by the Etruscans! The Vino Nobile wines we tasted were delicious. Our driver, Christina was knowledgeable and helpful. I wholeheartedly and without reservation recommend this tour to anyone interested in seeing the beautiful countryside of Val D’Orca and experiencing the exceptional wines of Montalcino and Montepulciano.
Mark P,Mar 31, 2026
- Review from Viator
A day we will never forget! The incredible countryside and fantastic wine were made even better by our guide. Paola was absolutely delightful, charming and incredibly knowledgeable of both the region and the wines. She made It fun and treated us like royalty. You could not pick better places to represent the magic of Tuscany. A special note- although the tour was to be 8 people, only my wife and I arrived so we had a private tour. I don’t think many or any other tour companies would have honored the commitment and followed through. For that we will be forever grateful.
Kirsten R,Mar 27, 2026
- Review from Viator
This was a really great tour and 10+ hours flew by. We loved every part of it from the wine tastings to the sightseeing to meeting new friends. It was a perfect day.
Panpan G,Mar 22, 2026
- Review from Viator
Excellent, strongly recommend. The tour offers a variety of wine tasting experiences, with depth and width. Our guide is excellent.
jessica b,Mar 11, 2026
- Review from Viator
This was a very unique tour and it was also very informative! I learned a lot about Montepulciano wine and the history of the region from the Ercolani cellar, which was where our first tasting was hosted. We tried some fabulous wines and cheeses there before going on to another town and then another winery. This tour was a fantastic!
Nicola C,Mar 10, 2026
- Review from Viator
Can’t express how good this was. Mike our driver is an encyclopaedia knows his history inside and out. First winery tasting in the tunnels at montepulcino was so interesting fabulous wines and Lucia was very knowledgeable about all the history. The second at montealcino was more modern but the host really knew her stuff. Excellent tour and well worth it
Lisa H,Jan 20, 2026
- Review from Viator
Simona was a wealth of information and so much fun! Gorgeous countryside, just enough history of the region and of Brunello. We had a perfect day. We had booked a group tour but only my sister and I showed so we basically had a private tour. Easy conversation, wonderful wine tastings (and purchases), a perfect lunch in Pienza (the soup!). I can’t say enough!
Katy P,Jan 7, 2026
- Review from Viator
We had a wonderful trip with Luca as our driver. There was so much to see and learn and it was just what I’d hoped for.
Wander53103486682,Jan 1, 2026
- Review from Tripadvisor
This wine tour exceeded all our expectations. Everything was beautifully curated and smoothly organized. The two wineries we visited were quite different from each other, yet both were excellent. Lunch in Pienza, a UNESCO World Heritage site, was also unforgettable. Paola, our tour leader, was amazing—warm, professional, and incredibly knowledgeable. It was simply a perfect day in Tuscany.
Todd H,Dec 30, 2025
- Review from Viator
Wine tasting to Montepulciano and Montalcino was great! Ask for Mike, he is a great driver and guide. Trip is well worth the time to see the Tuscany countryside and smaller villages.
Operated by Keys Of Italy / Florence