San Gimignano and Siena Day Trip: Explore Tuscan Villages With a Chianti Wine Tasting
4.3
2,940 Ratings
Firenze
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: 1 day learn more
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 hours of free time for a fascinating discovery.
  • Monteriggioni - A short distance from San Gimignano you will visit the charming historical hamlet of Monteriggioni (*), an amazing small medieval village enclosed by its famous walls, which remained standing to this day: free time for inside visit.
  • Chianti Road - From Monteriggioni, crossing the gently Chianti rolling hills, a short ride will take you to a cozy Winery, where you can relax and enjoy the fantastic world of Chianti with its wine and typical products: tasting of three fine wines and balsamic vinegar followed by a Chianti style lunch: 3 course with \
What's Included
  • Transport by G.T. air-conditioned coach with WIFI on board
  • Monolingual Visit in Siena (April to October)
  • 3-course Tuscan lunch at a Chianti Winery
  • Optional Siena Cathedral interior visit with entrance fee
  • Licensed Tour escort with live commentary
  • Optional shared round transport: coach, tour escort, lunch included
  • Tasting of Chianti Wines, 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

Engage in a full-day exploration at the core of Tuscany: San Gimignano, often referred to as the ‘Manhattan of the Medieval days’, is a renowned and visually pleasing hillside town in Tuscany. Experience the distinctive charm of Siena and its traditions through an extensive guided tour of the breath-taking old quarters. The charming small town of Monteriggioni and a quiet pause at a Chianti Winery for a traditional lunch which includes a guided tasting of 3 distinct wines and “vin santo”.

Please be advised that the order of the visits may vary.

(*) From November to March, the itinerary does not include the stop at Monteriggioni and the journey back to Florence is roughly 30 minutes earlier

  • A dress code is required to enter places of worships and selected museums. No shorts or sleeveless tops are allowed. Knees and shoulders MUST be covered for both men and women. This dress code is strictly enforced and you will risk refused entry if you fail to comply with requirements.
  • For small groups, up to 8 pax, the Tour escort service could be replaced with an English speaking driver-guide service, while maintaining unchanged the entire program of the excursion.
  • Comfortable walking shoes are recommended.
  • From November to March, the itinerary does not include the stop at Monteriggioni and the return to Florence is approx 30 minutes earlier
  • It is mandatory to arrive at the meeting point at the mentioned check in time. In case of delay it will not be possible to join the tour, nor to have a refund or reschedule the tour.
  • Clients with motor disabilities or wheelchair users are encouraged to notify the tour organizer in advance and seek medical advice to ensure suitability of services. Our tours and transportation are not suitable for people with motor disabilities or wheelchair users, so to prioritize the safety and well-being of all involved, the driver and tour manager retain the right to decline participation if they believe it may compromise safety. This decision rests solely with them, and no compensation will be provided in such cases. By accepting these terms, clients agree to respect decisions made by staff regarding participation.
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
4.3
(2940 Ratings)
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Sandra_g
May 26, 2024
Fun In Tuscany - An excellent tour at a good price. It was nice to see the real Tuscany. The lunch was good, the wine very good and the winery rep made the whole experience enjoyable.
Review provided by Viator
Tfintravel
May 26, 2024
Highlights of Tuscany - Great itinerary, sufficient time allotted in each city. Tour guide was very friendly, organized and knowledgeable. I would recommend if you only have a few days in the region.
Review provided by Tripadvisor
K4005tysamanthac
May 26, 2024
A trip to the past - Amazing. Was such a good tour. We loved walking through these slices of Italian history in the Tuscan countryside. And the lunch was just a cherry on top!
Review provided by Tripadvisor
Elizabethgraces2021
May 26, 2024
Best day in Florence!!! - Sandro was amazing!!! Such a fun experience🤍 the day was filled with sightseeing, good food, and fabulous wine. It is a must do while in Florence
Review provided by Tripadvisor
Chad
May 26, 2024
10/10 Great Experience - Sandro was an amazing guide. He made the experience seamless and enjoyable. I loved the wine tasting and the lunch served.
Review provided by Tripadvisor
Dennymcn
May 25, 2024
An awesome taste of Tuscany with fantastic guides - The tours guides Aaron, Rico and driver Marco were amazing. A fantastic tour with a good mix of activities and gorgeous little towns. I would highly recommend this tour for everyone.
Review provided by Tripadvisor
Juliaho1239pc
May 25, 2024
Amazing tour - The tour was amazing. The tour Guides were very kind and there were many things and beautiful spots to see. Best places to take pictures. Would do it again.
Review provided by Tripadvisor
Jeduthun
May 24, 2024
Amazing intro to Tuscany - I had such a fantastic day, it’s an amazing intro to the beauty that is Tuscany! Our guides Sandro and Fabiana were very kind and amazing and I loved that they kept their energy throughout the day. I also loved that they told us about the region’s rich history. I especially loved San Gimignano, I wish we had more time there! It was such a great start to the day. Lunch with the wine tasting was also such a fun experience - the lunch itself was delicious and hearty, I was so full. Our guide for the wine tasting was also very witty and fun. I’m so thankful for the experience that I had today, it’s one I will remember for a long time! If you’re too lazy to book train tickets like me, BOOK THIS TOUR!
Review provided by Tripadvisor
Margie_h
May 24, 2024
Lovely trip into Tuscany - Loved San Gimignano and the beautiful Tuscany countryside. It was great to leave the busyness of the city behind for a while. Aaron was an excellent guide. The bus was comfortable.
Review provided by Viator
Barbara
May 26, 2024
Beautiful scenery! - We saw a lot of beauty scenery and lovely old buildings. Sandro took us to San Giamannico first which was nice because it wasn’t busy. A long day but good.
Review provided by Tripadvisor
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up to 8 guests
1 Adult
June 2024
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