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)
5 stars
Reviews by Tripadvisor travelers
MariaLiviaCh, 12/12/2025 11:05:21 AM
We travelled with Ricardo and Enrico to Tuscany from Florence and had a great time. Ricardo was a friendly and informative guide and communicated clearly. The beginning of the trip was a bit unfortunate as the morning in San Giminiano was extraordinarily foggy and couldn't see much. Plus Montereggioni Fortress was closes and couldn't stop there. But from 12pm onwards the sun came out and everything went according to plan. The Il Cigliegio Restaurant was lovely, food delicious and plenty of drinks - we tasted 4 in total. They also have some cute animals like bunnies and geese roaming outside. In Sienna we booked both the tour and the Cathedral entrance. It's a good option if you want to learn more about the history and not have to worry about where to go. Also the Cathedral is gorgeous. This left us with just over one hour of free time. Keep this in mind when you book. Overall had a great day, worth seeing these beautiful cities.
Vera D, 12/12/2025 10:57:41 AM
Well organised, great information on tour, great knowledge of history, culture and local cuisine. The time on the bus is minimal, which was a great surprise for us and plenty of time to explore Sienna and San gimmiano, even if you partying all the organised tour. Definitely don't miss it
susan_k, 12/3/2025 3:13:54 PM
Awesome experience from being to end! The winery was wonderful and Cristiana or Catiana not sure about spelling was informative, kind and very friendly!
X5064OJjillr, 11/30/2025 12:34:41 PM
Cristiana was an absolutely amazing tour guide. She was very energetic and is extremely knowledgeable. Enrico was a great driver too!! Overall it was a great tour!
adityabV2680IE, 11/28/2025 11:11:26 AM
I recently took the Chianti, Siena, and San Gimignano tour, and it was absolutely fantastic. Federico, our guide, was knowledgeable, friendly, and attentive, making sure everyone enjoyed the tour at a comfortable pace. From start to finish, everything was well-organized, comfortable, and full of incredible sights.
V598YGsusanw, 11/28/2025 11:07:14 AM
Frederico was a great tour guide and Silvio was a perfect driver. Very knowledgeable and personable made the day extra special. We would happily go with them again on our next trip to Italy. Thank you.
Luke B, 11/23/2025 10:57:35 AM
Ricardo was very friendly and informative. It was just the right amount of time in each place. The lunch was delicious and the hosts were very attentive. We stayed in Florence and wanted to get out of the city to experience Tuscany. I recommend this as a great option to see what is outside of Florence.
Stefvasilakis, 11/21/2025 11:05:05 AM
Very nice experience. Ricardo our tour leader and stefano the driver were excellent. Don’t miss this tour Thanks guys 🙏
patrickhX8357HN, 11/20/2025 5:21:15 AM
We took the day trip from Florence to San Gimignano, followed by lunch at a Tuscan Winery offering Chianti and ended the day in Siena. The tour was excellent, well organized with enough free time to feel like an independent explorer. Marta our tour guide was friendly and oind with helpful suggestions of sites and experiences. Placcido our bus driver provided a smooth ride. The day started at 8am and we returned at 630p. Overall a great way to see Tuscany.
475KateH, 11/12/2025 7:51:02 PM
Loved this tour the places we visited were amazing and you had plenty of time to yourself. I like doing the guided tours as I like to hear the history. There is a bit of walking involved getting to the meeting spots which needs to be taken into account if you have any issues. it's a full day tour and i can't thank our guide Frederick and driver Hamil enough it was a lot of driving and a decent size group to manage.
- 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