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
(3695 Ratings)
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Saskgirl123
Feb 16, 2025
Wine tour - The tour guide Ricardo and driver Enrique were very good The first stop at the medieval san gimignano was very cool but being a Sunday not many places were open when we arrived. A must stop was the gelato to try a delicious authentic gelato. The winery stop at poggi was a delicious lunch and wine tasting experience our hostess was Leda was wonderful Sienna stop was interesting as well but we had a dual language walking tour and it was difficult to follow going back and forth between English and Italian. So would recommend making sure u have one language tour.
Review provided by Tripadvisor
Voyager33212051803
Feb 16, 2025
Beautiful day in Tuscany - We did a tour of Tuscany, it was a great day, all beautiful. We value Ricardo and Enrico’s willingness, kindness and sympathy
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Northstar610075
Feb 16, 2025
Excellent tour, would do it again - We loved the tour, you can visit the cities very well and taste some rich wines. Ricardo and Enrico very friendly at all times!
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S7821elmichelles
Feb 15, 2025
Excelent experience - It was a lovely experience to know a small piece of Tuscany. Our guide Alexandra was very nice and ponctual, as our driver Giovani. The wine tasting was wonderful. I recommend it very much.
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Dane
Feb 15, 2025
Beautiful tour of tuscany. - 4.5/5. Alexandra was Very informative and Friendly. Fun day out to explore the beauty of tsucany. Siena is a must! Great experience
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Carmenhh7947jk
Feb 12, 2025
Genial - Very well organized excursion, spots, guides Ricardo and Jenaro the driver, until next. Recommended. 🫠🫠🫠🫠🫠🫠🫠🫠🫠
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Pioneer25151911377
Feb 12, 2025
Nice chill tour with a great lunch and great wines - We chose the option for free time in Siena (no guided tours) and just went around. It was nice and chill, spending over 2 hours per location. The lunch was a nice and simple, but delicious. In total we tried about 4 types of wines per person, one to start and 3 with the meal.
Review provided by Tripadvisor
320shawnah
Feb 16, 2025
Excellent wine tour/tasting! - A full day with an excellent lunch and tasting of wine, olive oil and balsamic vinegar. The walking tour in Siena was good and SanGimano was a nice place to visit although we were early and many places were not open. The gelato was excellent as recommended by our tour guide Ricardo. Enrique was a very friendly and good driver.
Review provided by Tripadvisor
Jabou55
Feb 12, 2025
Very nice excursion - A very nice day of excursion despite rainy and foggy weather that could not highlight the beauty of Tuscany as it deserves. Ricardo was a great guide, taking the time to answer questions, and with good recommendations you can trust him! For the meal break we were very warmly welcomed in a family establishment where the majority of products are made on site. On the menu antipasti , pasta al ragu, and cupcake with almonds, all accompanied by different types of wines in a friendly setting. In short a busy day that I recommend to get off the trails of big cities.
Review provided by Tripadvisor
Hbcl55
Feb 12, 2025
A beautiful discovery of Tuscany despite the rain - We spent a great day exploring Tuscany! The organization was well thought out, with a perfect balance between visiting time and breaks. The meal was delicious, and our guide Riccardo gave us clear explanations in English and Spanish. Only small downside: the rainy weather did not allow to fully enjoy the beautiful landscapes. But this is still an experience to recommend to discover this beautiful region!
Review provided by Tripadvisor
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