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
(4097 Ratings)
5 stars
4 stars
3 stars
2 stars
1 star
249heidyn
Jul 18, 2025
Best tour guide ever! - Sandro is amazing, very kind , patient and accommodating. We would love to go on a different tour in the future and have him again as our tour guide.
Review provided by Tripadvisor
Lenny
Jul 18, 2025
Awesome tour !!!! - Had an amazing experience with Sandro as our tour guide. He is extremely knowledgeable and has a very friendly personality.
Review provided by Tripadvisor
_f1200ag
Jul 18, 2025
My perfect day) - Very nice journey-a lot of experience,emotions and beautiful memories. Sandro is perfect guide-not boring,very positive and gives a lot of useful information And the dinner and degustation in winery was really fantastic!Such an atmoshere!I felt a real Toscana!!! Thank you,hope to see you again
Review provided by Tripadvisor
Mariadh7554td
Jul 18, 2025
- Sandro was an amazing tour guide. He went above and beyond what a tour guide should do!!! An amazing experience!!! I would recommend this tour and request Sandro as your Guide
Review provided by Tripadvisor
Jessica_s
Jul 16, 2025
Shane train - Lots of wine drinking makes this a fun trip! Aaron and Antonio did a fantastic job leading the trip and driving.
Review provided by Viator
Gjimson1
Jul 13, 2025
Love the wine - Wine tasting was well worth it. Lunch was delicious. Love Siena too; took the guided tour option to the church which I recommend.
Review provided by Viator
Richard_r
Jul 11, 2025
Very informative guide... - Very informative guide (Hilary) who took us through the beautiful Tuscan countryside & medieval villages
Review provided by Viator
Lmc52
Jul 11, 2025
A great way to visit the region in a day. - Fabi our guide was great, took good care of us (driver also very good and the coach was very comfortable) she gave us just the right amount of information to enjoy our trip. We had a great day and would recommend for anyone who has a few days in Florence to get out and see the wider region.
Review provided by Tripadvisor
Marie_n
Jul 8, 2025
The Sienne and co tour. - Punctual departure, Alessandra (our guide) and Ferdinando, our bus driver (I hope I got his name right) were excellent. Alessandra explained everything in English and Spanish. She was very attentive to details.
Review provided by Viator
Carlos
Jul 7, 2025
Unforgettable tourist experience - Excellent tour and guide team. I am very grateful to guide Marta for turning this tour so wanted by us into an unforgettable experience with her guidance and explanations in every place we visited. We also thank Silvio for leading us peacefully and safely along the roads of Tuscany. Certainly on our next return is an experience that we will do again and recommend to everyone.
Review provided by Tripadvisor
From $92
up to 8 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).