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
(3635 Ratings)
5 stars
4 stars
3 stars
2 stars
1 star
559jazm_nm
Dec 11, 2024
Get to know Tuscany, an AMAZING tour, places and tour guide! - The tour was simply PERFECT! We started the day with a perfect sunny weather, our tour guide was Sandro and he was A MA ZING!! So cheerful and you can just sense and he transmits, that he loves what he does, and that he loves and knows the places and local people as well! The places are beautiful, the wine and the food delicious, you have PLENTY of time to discover the places by your own. Don't think it twice, you are absolutely not going to regret it (and better if Sandro is your guide, and I don't want to leave aside our driver Gennaro, because he got us safe and on time to all the locations!) TOTALLY recommend this tour!
Review provided by Tripadvisor
19shylam
Dec 11, 2024
Amazing tour with Sandro - This tour is absolutely incredible. Recommend doing it earlier in the day because the afternoon gets extremely busy with tour groups and it becomes harder to get clear pictures. The vineyards and countryside are breathtaking and the winery and tastings were an added bonus. The guided tour in Siena is well worth it and the town is rich in beauty and history. Sandro the tour guide was fantastic spoke multiple languages and made everyone feel like family. Can’t recommend this experience enough
Review provided by Tripadvisor
Minerval339
Dec 9, 2024
It has been fantastic, very complete and the guide Alexandra exceptional, very good explanations and and your Spanish very good. - Very complete, very well organized. Great visit to Tuscany in a day. We have eaten in a winery very well and with a wine face. Lovely. I recommend it 100% Thank you for the day we spent.
Review provided by Tripadvisor
Hollybj801bg
Dec 8, 2024
Great Day in Tuscany! - Our leader Gabriele was excellent and incredibly knowledgeable. He kept us moving from location to location with ease! Our driver Giovanni was such an impressive and professional driver. I would highly recommend this tour and Gabriele and Giovanni to anyone looking to enjoy the beauty of Tuscany.
Review provided by Tripadvisor
Gregorybl5673kh
Dec 8, 2024
Lots of fun - Gabriela was a great, informative, and funny tour guide! He gave us all the interesting information at the appropriate times and made the tour entertaining.
Review provided by Tripadvisor
605sergiub
Dec 7, 2024
Nice experience in Tuscany - We had Riccardo as our guide and Marco as our driver -very professional both. The tour went perfect. A lot of useful informations were provided. I would definitely recommand the full tour - the cathedral in sienna is a must!
Review provided by Tripadvisor
Jean_c
Dec 5, 2024
What a lovely experience exploring new places with a wonderful guide! - I loved wondering around San Gimignano! The town has a fairytale look and it was just beautiful! Our experience wine tasting was so fun and so many interesting elements to see and learn about. The lunch was perfect and delicious. This was my first time to experience wine tasting and it will never be forgotten. I loved Siena despite the rain, it did not dampen our experience. Our guide was so informative as she gave the history of this little town. The cathedral was grandiose! Our guide, was delightful, fun and full of history for the area. She made us love every minute. The bus driver did an amazing job and made us very comfortable in this great bus, on this great trip.
Review provided by Viator
Angeline_k
Dec 9, 2024
Missing Monteriggioni… - I have done this tour 4x with this same company and waited to take this tour again with my new husband this time. Everything was wonderful - we opted to come during the slow season to avoid crowds of people. However, my only complaint is that Monteriggioni was closed for the winter so we did not visit that location. They could have let us have that extra time in Siena, where things were rushed & chaotic due to the crowds of people there for the Christmas market. We ended up arriving back in Florence over an hour early.
Review provided by Viator
Juac26
Dec 6, 2024
Tour of Tuscany - The ride itself was great! It's worth seeing. By the time of year, there was no Monteriggioni. In Siena, it is worth taking the tour with the Cathedral, which is stunning and has a guide specific only to the city of Siena. The lunch was in a very nice winery, but the wines with salty prices and the lunch was a penne a bolonhesa.
Review provided by Tripadvisor
522isabelf
Dec 7, 2024
The food of the excursion was not very good and also scarce. - It's nice San Gimigniano and Siena, and the guides were good and friendly, giving explanation of everything... When it was winter we didn't see Monteriggioni. Nor could we enjoy the vineyards and the Tuscan landscapes. Lunch in Chianti was lax, and wine tasting more than regular.
Review provided by Tripadvisor
Select Date and Tickets
up to 8 guests
1 Adult
December 2024
Sun
Mon
Tue
Wed
Thu
Fri
Sat
Today