Ultimate Tuscany: Medieval Gems & Chianti Wine Day Trip
Discover Tuscany in one day from Florence. Begin in the hilltop UNESCO town of San Gimignano with about 2 hours of free time to explore towers, lanes, and artisan shops. Continue to Monteriggioni (seasonal; see note), a perfectly preserved walled village, with time to wander inside the walls. Cross the rolling Chianti hills to a cozy winery for a tasting of three wines and a three-course farm-to-table lunch, ending with cantucci & vin santo. In the afternoon, enjoy a guided walking tour of Siena: stroll Piazza del Campo and see the Palazzo Pubblico, then admire the Cathedral (interior visit if option selected). Finish with free time before returning to Florence. Please note that the order of the visits may change (*) November to March, the Tour does not include the stop at Monteriggioni and the return to Florence is approx 30 minutes earlier
Reviews
Reviews and Rating (Tripadvisor)
4 stars
5 stars
Reviews by Tripadvisor travelers
Wayne_B, 11/3/2025 3:55:00 AM
Excellent tour guide (Ricardo) and driver, Alessandro. It was a long day for sure but worth the ride!
Daniel_G, 11/2/2025 3:18:58 PM
Ricardo, Alisandro and his team were fantastic. Ricky knew his stuff inside and out, was genuine, funny, engaging and very pleasant to be around all day. Alisandro was fantastic behind the wheel all day without a hiccup. Thanks for the fantastic day.
guido_mitolo, 11/2/2025 11:08:11 AM
Anyone should at least take a day trip to visit the region of Tuscany. This day trip is worthwhile. The tour guide, Ricardo, is knowledgeable, easy to understand, and funny. The driving is safe and comfortable. In each visit, we had enough time to appreciate the views. The lunch stop was very complete. We drank a lot of wine of different types, and the food was plenty. I recommend this trip.
zuerc2025, 11/2/2025 11:06:52 AM
We had an amazing time & authentic experience with Ricardo (guide) & Alessandro (bus driver) in our day tour at San Gimignano & Siena! Highly recommended if you are visiting Florence.
Joan M, 11/2/2025 11:05:26 AM
Ricardo & Alex were excellant. The inntinery was well planned . The guide in Siena was hard to hear and understand . Enjoyed the lunch. Highly reccomend.
kennedyr675, 11/2/2025 11:02:55 AM
Riccardo aka ricky was a great guide!! He was welcoming and showed great spirits throughout the trip. Flow of the tour was well paced and all expectations e.g meeting time/location were clearly communicated.
tinasI7645AV, 11/1/2025 5:15:38 PM
Ricardo was a very knowledgeable and friendly tour guide and our driver Jacob made sure we got to each destination safely. We found the tour well paced and enjoyed the free time we had to take in the beautiful sights. Thank you!
X7495GAchristiner, 11/1/2025 1:13:13 PM
Knowledgeable tour guide; provided just the right amount of information; friendly and very accommodating when a member of the group was feeling under the weather.
Shawn K, 11/1/2025 11:58:40 AM
We booked our trip through Klook, and our tour guide Ricardo (CAF tour) made the San Gimignano and Siena tour truly memorable. He shared a wealth of interesting insights throughout the journey, and everything was well organized from start to finish. The winery lunch was fantastic, and special thanks to Ricardo and our bus driver for the smooth and enjoyable ride!
Mari_L, 10/31/2025 6:36:12 PM
Guide Alejandra was knowledgeable and give us the information in English and Spanish. The three medieval towns were charming and worth visiting as well as the family owned winery and olive oil producers. The Tuscan meal was simple (typical) and good. The family vineyard owners were charming and friendly so we had a lovely time. Their gift shop was good and we were lucky to have just been able to buy the new production of extra virgin olive oils for 2025 which were available just this week!!! Their dessert wine was delicious so we bought a bottle. All in all it was a fun experience. We did have an issue at the end when the local guide did not return us to our meeting spot and we had to find our way there (not easy in a medieval town full of tiny crooked streets). Then upon meeting up with our Viator guide Alejandra at the appointed time of 5:30 pm she left us and 8 other tourists at the meeting point and left for the bus !!!! We waited for her at the meeting point not knowing she had left to the bus!!! We had some tense moments (20 minutes) and finally had to contact Viator who told us to get to the bus quickly or lose our ride back to Florence!!! The end was not fun but we all made it back to Florence!!!
- Infants and small children can ride in a pram or stroller
- Public transportation options are available nearby
- Specialized infant seats are available
- Travelers should have at least a moderate level of physical fitness
- 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 or no show it will not be possible to join the tour, nor to have a refund or reschedule the tour.
- Please be advised that it is required to bring your original ID with you during the tour.
- Once the audio guides are handed over before the guided tour, they become the full responsibility of the customer. In case of loss, a fee of €80 will be charged.
- 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.
Departure point
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.Return details
Discover Tuscany in one day from Florence. Begin in the hilltop UNESCO town of San Gimignano with about 2 hours of free time to explore towers, lanes, and artisan shops. Continue to Monteriggioni (seasonal; see note), a perfectly preserved walled village, with time to wander inside the walls. Cross the rolling Chianti hills to a cozy winery for a tasting of three wines and a three-course farm-to-table lunch, ending with cantucci & vin santo. In the afternoon, enjoy a guided walking tour of Siena: stroll Piazza del Campo and see the Palazzo Pubblico, then admire the Cathedral (interior visit if option selected). Finish with free time before returning to Florence. Please note that the order of the visits may change (*) November to March, the Tour does not include the stop at Monteriggioni and the return to Florence is approx 30 minutes earlierRedemption
• Check-in time and Meeting Point: at 7:45 am at Piazzale Montelungo, 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. How to reach the meeting point from Santa Maria Novella Station Square: Take "Via Valfonda" (Valfonda street) and go straight on at the end of the street, until you see the Fortress (Fortezza da Basso). Cross the street in front of you and keep your left side, until you see on the right side Piazzale Montelungo (big square with car and Bus parking) 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. Once the audio guides are handed over before the guided tour, they become the full responsibility of the customer. In case of loss, a fee of €80 will be charged. Please be advised that it is required to bring your original ID with you during the tour. - For small groups, up to 8 pax, the Tour will be by Minivan and the Tour escort service will not be provided. The remaining services will be as scheduled. - It is recommended that participants wear comfortable shoes and appropriate clothes to visit museums or places of worship. • Our Contacts: Agency address: via dei Tavolini 15red - 50122 Firenze - Phone +39 055 29.55.72 or +39 055 28.32.00 - Whatsapp: +39 3458025842 email address: tours@caftours.com24 hours before travel date - 100% refund
Less than 24 hours before travel date - 0% refund