Private Tour
Available languages
Mobile ticket
Embark on a private, guided journey through the picturesque vineyards and historic cellars of Montepulciano, the home of the celebrated Vino Nobile di Montepulciano. This exclusive tour offers an immersive experience that captures the essence of Tuscan winemaking tradition.
What to Expect
Guided Visits to three renowned Wine Estates:
Explore estates with centuries of winemaking expertise.
Learn about the intricate process of crafting Vino Nobile di Montepulciano from passionate experts.
Exclusive Wine Tastings:
Savor a curated selection of exquisite wines at each estate.
Lunch at the Second Estate:
Indulge in a traditional Tuscan meal paired with exceptional wines.
This intimate experience blends Tuscan culture, history, and gastronomy into a memorable day amidst the stunning countryside of Montepulciano. Whether you're a wine enthusiast or simply looking to enjoy a luxurious day in Tuscany, this tour is the perfect choice.
Specialized infant seats are available
Service animals allowed
Infants and small children can ride in a pram or stroller
Transportation options are wheelchair accessible
Wheelchair accessible
Suitable for all physical fitness levels
Minimum drinking age is 18 years
Please advise any specific dietary requirements at time of booking
All sales are final. No refund is available for cancellations.
Val D'Orcia
They will be able to stop and admire the breathtaking surrounding countryside.
Montepulciano
Time for a brief visit to the city.
Private tour
Wine tasting
Tour escort/host
Round-trip private transfer
Snacks
Lunch
Gratuities
Select a pickup point
Traditional lunch
Pickup included
19 reviews
Total reviews and rating from Viator & Tripadvisor
Adventure38209519549,Apr 26, 2026
- Review from Tripadvisor
Our day was amazing. From the minute we met Francesco & the other 2 couples on our tour we knew we were in for a treat. The drive into the Tuscan countryside is worth the trip alone, but when you get to the wineries & meet the people and learn their process, the whole experience comes to life. Francesco was extremely knowledgeable but shared information in an easily digestible & understandable way that left you wanting to hear more about this beautiful place. We learned so much about Italy, wine, the winemaking process and how to truly appreciate it all. Highly recommend to anyone who loves wine, good people & a great time.









P9065JLlaurenb,Apr 15, 2026
- Review from Tripadvisor
We had the pleasure of visiting 3 wineries with our Somolier Francesco during our 8 day stay in Cortona. Francesco opened our eyes in so many ways. He taught us how to really taste and experience wine, olive oil, and fresh foods with an open mind and a clean palette. He made our day, and frankly, our trip the best ever! I will forever treasure our wine adventures and encourage anyone visiting Tuscany to request Francesco with "Do it in Tuscany" for the finest elevated vino experience!



andrewfR5973YT,Dec 9, 2025
- Review from Tripadvisor
Our tour guide and Wine Sommelier Francessco was wonderful! The three estates we visited were specifically chosen by him and we loved visiting all of them. We were able to have lunch with the owner of Villa S. Anna which was a highlight as she shared cantatas stories.


ruthd191,Nov 11, 2025
- Review from Tripadvisor
Francesco was our guide for the tour. He was very knowledgeable about wine and the vineyards we visited. He explained the wine making process and the various grapes used in each wine. The best part was the explanation of how to pair wines with food and how to smell and taste each wine. Francesco was very pleasant and personable. We thoroughly enjoyed our day with him exploring the three vineyards.
TBD77,Nov 1, 2025
- Review from Tripadvisor
Francesco was incredible! He is so knowledgeable (and opinionated). He was a lively, fun, smart guide! And he chose perfect vineyards for us and I loved the strong women leading the tours. We ordered wine and olive oil to be shipped home. It was truly a delightful day! Francesco was very kind and caring with my mom who has mobility issues & great about sharing so much knowledge about the land and area we were in! I would recommend this tour for anyone!









S5932FLes,Oct 27, 2025
- Review from Tripadvisor
Great driving tour for a diverse wine experience. Francesco was excellent and really made the trip exceptional. Expert navigator through the nuances of the Tuscan wine region. Somewhat off the beaten path which may the exposure that much more special. Highly recommended!

Patrice C,Oct 14, 2025
- Review from Tripadvisor
I worked with Federica at DIIT to plan several activities for four couples staying at a villa close to Siena…. 2 full day wine tours with our own personal “sommelier/driver” Francesco who made our time so educational as well as keeping us laughing along the way. And we seemed to eat and taste ourselves silly! Federica also provided a personal chef to cook for us at the villa for two nights…. As well as Chef Elaina who came to the villa to teach us the art of making some delicious traditional Tuscan cuisine. Last but not least, we were set up with a lovely tour of Siena. Cannot say enough about how helpful Federica was in providing us with a truly authentic Tuscan experience!!!










Q2855EGjonh,Oct 12, 2025
- Review from Tripadvisor
Spent the day being hosted by Francesco who was wonderful. He was patient and informative on everything “Tuscany”. We especially enjoyed the home style lunch with Simone at Villa S Anna. We felt honored learning from her. Great experience and a memorable experience! Grazie!



BaconBoss,Sep 23, 2025
- Review from Tripadvisor
Family of 8 adult family/couples spent a wonderful day with our guide Francesco exploring 3 unique vineyards, ranging from large to small, each with unique backgrounds and friendly, welcoming owners. Francesco possessed a wealth of wine knowledge that he happily shared with our group and our relaxed lunch while tasting at Villa St Anna was a great midday break. Opportunities to purchase wine and olive oil but no pressure, lots of information and learning along the way as well!






David F,Sep 21, 2025
- Review from Tripadvisor
Didn’t extreme great job of explaining the wyns and food to us while we were out there. Would highly recommend. thought we knew a lot until Francesco explained it all to us even better.
Operated by Do it in Tuscany