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
(3918 Ratings)
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Ryan_k
May 4, 2025
Great tour, highly recommend - Fun trip! Sandro was a great guide with help from Silvia. Every stop had something to offer, and nothing seemed overly rushed. The wine tasting was just ok, felt more like a scripted factory and we had better house since for cheaper in the cities, but it was still a fine experience. Siena was great - if you are book, don't cheap out - buy the cathedral/duomo ticket, it's amazing. Great tour, well organized, driving time might have been 3-3.5hrs total but didn't feel like it and helps you take a break from the walking!
Review provided by Viator
Slobodanc37
May 3, 2025
Perfect excursion - Realy fabulous. Well tailored, professional, precise and charming. Realy devoted, concentrated on group. Thank you so much !!!
Review provided by Tripadvisor
88krinas
May 3, 2025
Great tour with amazing guide! - Sandro was amazing at organising the day and showing us the best parts of Tuscany! Great itinerary, comfortable coach and nice food and wine. Also accommodates for vegetarians!
Review provided by Tripadvisor
Amosl777
May 3, 2025
Tuscany tour - Sandro was knowledgeable and shared many fun facts and history about the places we visited, even places that were along the way. Overall the tour was fun and engaging and enough time was given at each location to explore
Review provided by Tripadvisor
488lillyg
May 3, 2025
Tour with Sandro - We had Sandro as our guide and he was fantastic. Perfect person for this job, has a lot of patiences and passion for this job
Review provided by Tripadvisor
Balt12
May 3, 2025
Fantastic day and hosts! - What a fantastic day and tour. The tour was extremely well organized and offered in multiple languages. Martha and Giovanni (driver) were hospitable, inviting and fun. There was plenty of time at each stop to enjoy the towns. Lunch was very good. No pressure to buy at the winery (but we did, because it was very good :)). The tour started and ended in a very convenient location. It was a little difficult to find so give yourself a little extra time, if walking.
Review provided by Tripadvisor
Chadia_m
May 2, 2025
A Must try - A wonderful experience. I enjoyed every place we visited. Each has a different charm and history. The tour was amazing and got to share this experience with people from all over the world.
Review provided by Viator
Sarah_g
May 4, 2025
It was ok - The tour was really good. Lunch for us was just ok but others seemed to really enjoy it. The wine and winery were wonderful. The Cathedral and that area had way to many people in it. You couldn’t even hardly move. They need to limit the amount of people they let in the Cathedral at one time. The walk ways outside are not that big and when you have that many people in it, it makes it not enjoyable. Our tour guide Sandro was wonderful.
Review provided by Viator
Freedom52387451762
May 3, 2025
Tuscan wine tour. - The views and history were awesome. Our guide Sandro was excellent. He was very helpful and smart. Knew several languages, which is impressive. The lunch at the winery was not very impressive. Pasta was hard and lacked much meat and sauce. Overall, Great experience.
Review provided by Tripadvisor
Janice_o
May 1, 2025
Day tour of Tuscany - It started well but went downhill after lunch when we had to wait for an hour for our tour of sienna
Review provided by Viator
From $89
up to 8 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).