San Gimignano and Siena Day Trip: Explore Tuscan Villages With a Chianti Wine Tasting

Embark on a full-day tour to San Gimignano and Siena, exploring the charming Tuscan villages and indulging in a Chianti wine tasting. Discover the medieval beauty of San Gimignano, immerse yourself in the traditions of Siena, and enjoy a delicious lunch at a Chianti winery.

Duration: 11 hours
Cancellation: 24 hours
Highlights
  • San Gimignano - Your memorable journey starts with the charming San Gimignano, world famous walled town located on a hilltop, which remained intact through the centuries, renowned for its tall towers, wonderful frescoes and many other valuable works of art: here the tour leader will lead you to the historical center, where you will have around 2…
What's Included
  • Siena Cathedral interior Guided Visit including entrance fee (if option selected)
  • Licensed Tour Leader with live commentary on board
  • Monolingual Visit in Siena (April to October)
  • 3 course set-menu typical Tuscan lunch in a Chianti Winery
  • Transport by G.T. air-conditioned coach
  • Local guide in Siena (if option selected)
  • Tasting of three different Chianti Wines, extra virgin olive oil & “vin santo”
What's Not Included
  • Our Shared Round Transport option does NOT include: Siena Guided Visit, Cathedral admission
  • From November to March, the itinerary does not include the stop at Monteriggioni
Additional Information

Discover the timeless allure of Tuscany on an immersive full-day journey! Step into the enchanting past of San Gimignano, often dubbed the “Manhattan of the Middle Ages” for its towering skyline. Traverse its cobblestone streets, steeped in history, and soak in the panoramic views of this captivating Tuscan hill village.
Next, delve into the cultural…

Location
Piazzale Montelungo
Check in time: 07:45am - Montelungo Square, at the end of the ramp connecting with the train station. An assistant will be waiting for you wearing blue clothing with CAF Tour - Gray Line logos.
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
4.4
(4282 Ratings)
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Ernies53
Oct 3, 2025
Amazing guides - It was wonderful. Lilly and Hilaria are awesome. Would recommend the trip. The sights are just incredible. Book the trip ahead of time.
Review provided by Tripadvisor
Jorge
Oct 2, 2025
Great tour - Great places visited, the tour guides were very nice and helpful (Lily, Riccardo and Enricco). Would definitely recommend booking this tour.
Review provided by Tripadvisor
Danielcx1580we
Oct 2, 2025
We recommend this excursions to everyone! - They were very informative and forward clear instructions. Ricardo and Lili were awesome Enrico, the driver was excellent, turning all corners sharply! Amazing. San Gimignano is a very nice city, worth while to visit, you will fall in love with it. Siena is also very nice, we were able to by tickets to visit the Duomo where we admired the artworks and sculptures for which were unbelievable made by hands. The stop at the winery was great as well, Poggo Al Laghi in Monteriggioni was great, Marco was a great host. We made a quick stop at the fortification in Monteriggioni which was a surprise stop by so beautifully stuck in time! We could have stayed there all afternoon! Great excursion that we are recommending to everybody and with Ricardo and Lili, you can’t ask for better guides! Daniel
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736sweetl
Oct 2, 2025
Very enjoyable tour - Well organised. Riccardo, Lily & driver Enrico was very efficient, organised & knowledgeable. Everything ran smoothly
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Charlotted2663
Oct 2, 2025
Wonderful tour seeing the sights of Tuscany - We had a lovely tour with Riccardo, Lily and our driver Enrico, and also the local tour guide in Siena. It was well planned out and the guides were very helpful. Lunch at the winery was delicious too. San Gimignano was especially beautiful.
Review provided by Tripadvisor
269karena
Oct 2, 2025
Worth the Trip! - Awesome- Lili, Rick and Edourda entertained us for a wonderful day trip which include a lunch tasting in a wineyard Everything was well organised and explained Highly recommend 👌🏼
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R5031kdmatth
Oct 1, 2025
Beautiful scenery and wonderful knowledge - This was one of the best days of our five week trip throughout the UK, France and Italy! The scenery was absolutely amazing and it was certainly great to get fabulous information from our guide Fabi. She was very knowledgable in two languages! Loved all the sites we visited and had plenty of time to explore and get photos. If you aren't doing the Duomo tour in Sienna the 3 hours before leaving can be a little long, but that was my only, very mild negative. Great experience, would definitely recommend.
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Quintonp865
Sep 30, 2025
Amazing medieval tour. - This was an outstanding tour. Fred was a great tour guide, extremely knowledgeable and had a good comedic timing with some of his bits of information which I find fun. Highly recommend doing the full tour (cathedral package) as the duomo in siena is breath taking. Originally I did not include it in the package but after seeing the outside I quickly went and bought tickets to get in. Ferdinand was a great bus driver and was smooth ride all the way.
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A127kdsarag
Sep 30, 2025
Smooth Ride, Great Wine, and a Wonderful Guide Fred - Amazing Tuscany Day Trip with Excellent Guide! We had an absolutely wonderful time on the Tuscany day tour! Our guide, Fred, was incredibly nice and helpful throughout the entire trip. He went above and beyond to assist us with any issues and made sure everyone felt comfortable and well taken care of. The vineyard we visited was a true highlight—the wine was delicious, and the setting was simply picturesque. The itinerary was very well-planned, allowing us to enjoy each spot at a relaxed pace without feeling rushed. Additionally, our driver did an excellent job. The ride was smooth and comfortable the whole way, which made the journey even more enjoyable. Overall, it was a perfect day trip—highly recommended for anyone looking to experience the beauty of Tuscany in a comfortable and enjoyable way!
Review provided by Tripadvisor
Shelbylq4499hr
Sep 30, 2025
An amazing Tuscan experience!! - This was such an amazing time! We decided to do this last minute & are so happy we did. Fred was an amazing tour guide, very knowledgeable, very personable, & really helped make the experience all the more enjoyable! The bus right was smooth as can be, thanks to our driver Ferdinand, & was very comfy for the transitions between stops. All the stops had so much to offer & was a great way to see the beauty of Tuscany that you may not have been able to see otherwise. Thank you Fred & Ferdinand!
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From $93
up to 8 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).