Ultimate Tuscany: Medieval Gems & Chianti Wine Day Trip
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 richness of Siena as your expert guide unveils its treasures during a comprehensive tour of the spellbinding old town. Immerse yourself in the traditions and heritage that make Siena an icon of Italy. Explore the quaint Monteriggioni Hamlet (*). Then, prepare your senses for a typical Tuscan lunch, while savoring exquisite wines, each sip telling a tale of the region’s rich viticulture, a perfect finale to your day in Tuscany's heart. 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)
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Reviews by Tripadvisor travelers
heathm826, 10/21/2025 11:37:43 AM
Enjoyed all facets of the experience. Sandro’s organisation of such a big tour group ensured we had plenty of time to enjoy our lunch and the sumptuous wines. His mastery of languages and local knowledge was a bonus.
565jeniferg, 10/21/2025 11:33:08 AM
The bus came about 45 minutes late, but Sandro (our tour guide) was great and kept us rolling and on schedule after that. It was a fun experience. If you like history, pay extra for the tour and cathedral part. If not, wandering around Siena is a blast :)
Excursion45983566960, 10/21/2025 11:32:53 AM
Sandra - was amazing! Involved and kind. My complainant isn’t at all about him, the bus was late which meant we had less time at each place in order to stay on time.
Brett_S, 10/21/2025 3:30:51 AM
Visited lovely little villages and had free time to explore. Tour leader was friendly and helpful. Lunch was acceptable (appetiser was good, pasta main was average and no desert as promised, just a small biscuit). Wine was really nice but too expensive to buy. Overall worthwhile.
PhilipR_S, 10/19/2025 2:39:38 PM
This tour was well worth it. We enjoyed discovering the medieval towns inTuscany, lunch was tasty, bus was comfortable. The three staff assigned to our tour were Alexandra, Stella & Nino and they were all lovely & wonderful! Highly recommended tour!
Chad_W, 10/19/2025 10:32:10 AM
A great way to visit some of Tuscany. Takes a day but well worth the time. Dani , Sharon and Placido were outstanding guides. Thankyou
qiuyunl2025, 10/18/2025 12:20:53 PM
Nice tour! Our guide Stealla is Friendly and the bus is clean on time. Loved the wine tasting and lunch was good . The staff at the winery is freindly and funny.
106karstena, 10/18/2025 12:13:56 PM
The guide was really Nice. The toscana is a place very very beautiful. I Loved san girminiano. The gelatto from dondelli really worth his title
DeborahBenelli, 10/18/2025 12:12:58 PM
Was lovely! The wine tasty I was expecting more understanding and explanation about the wine production process. Was more eating.
Junaz_A, 10/17/2025 5:30:18 PM
Beautiful towns, gorgeous food and lovely hosts! The tour started on time and it was well organised. The bus was very comfortable with free wifi and plugs for you to charge your phones. Our hosts were very accommodating and attentive to our needs. Many thanks to AARON and LILY for being our guide and to PLACIDO for driving us to our destinations safely.
- 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 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 richness of Siena as your expert guide unveils its treasures during a comprehensive tour of the spellbinding old town. Immerse yourself in the traditions and heritage that make Siena an icon of Italy. Explore the quaint Monteriggioni Hamlet (*). Then, prepare your senses for a typical Tuscan lunch, while savoring exquisite wines, each sip telling a tale of the region’s rich viticulture, a perfect finale to your day in Tuscany's heart. 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