Florence Day Trip: Chianti Wine Tasting, Siena, San Gimignano
Overview
Available languages
9 hours
Mobile ticket
Experience the best of Tuscany on this Florence day trip to Chianti, Siena, and San Gimignano. Enjoy a Chianti wine tasting at a local estate, explore the medieval streets of Siena and San Gimignano, and savor a delicious Tuscan lunch with regional specialties included in your tour. Led by a local expert guide, this small-group tour combines culture, history, and food for the ultimate Tuscan adventure.
Additional Info
Public transportation options are available nearby
Specialized infant seats are available
Suitable for all physical fitness levels
This tour is in English.
Unfortunately due to the nature of this tour it is not suitable for guests with mobility impairments or with wheelchairs, or strollers.
This is a walking tour. Guests should be able to walk at a moderate pace without difficulty.
Those with dietary restrictions need to contact us after booking the tour so we can arrange your lunch. Unfortunately, we cannot accommodate vegans or those with celiacs.
Tickets for the Siena Cathedral are not included in the tour price. If you wish to visit the Cathedral, your guide will assist you. The Cathedral is closed on Sundays and for certain holy days.
In order to get into the city center, we utilize small luxury minivans. This allows us to avoid the parking lots outside of the center requiring us to walk. Your guide may need to split time between vehicles on groups larger than 8.
Walks and Devour comply with all local government regulations. Please refer to local government guidelines for the most up to date information.
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
What‘s Included
Expertly guided walking tour of Siena
Expertly guided walking tour of San Gimignano
Expert English-speaking guide
Designated professional driver
Gourmet lunch and wine tasting in Chianti
Air-conditioned transport
Gratuities
Hotel Pick-Up/Drop-Off
What To Expect
Tuscany
Your driver and guide will pick you up in a comfortable, air-conditioned transport in central Florence and drive you through the hills of Tuscany. You'll pass the best panoramic viewpoint of Florence and pause for pictures.
Siena
Siena is one of the best-preserved examples of medieval Italian architecture in the world. Spared German bombing in WWII, this time capsule of ancient, precarious-looking buildings is home to the Palio, one of the greatest and most dangerous horse races in the world.
Options
Small Group Tour
Group Tour
Private Tuscany from Florence
Siena, San Gimignano & Chianti
Reviews
243 reviews
Total reviews and rating from Viator & Tripadvisor
5 Stars for Sandra
David P,
Sep 7, 2025
- Viator
5.00This trip was just absolutely amazing!!!! Sandra was excellent and gave us so much detail about the local areas of Sienna and San Gimignano. Both cities were amazing with the architecture and history of the buildings. Our trip was sandwiched between our wine tasting and lunch. The lunch provided was 5 star and not to give it less of importance, the wine tasting turned into so much more!!! The balsamic vinaigrette was the best ever - that was just the tip of the iceberg. The wine was some of the best we’ve had including the top black rooster chianti was superb. Overall, this was a 5 star trip!
Fantastic!
Sue P,
Sep 3, 2025
- Viator
5.00It was great. Our tour guide and driver were very friendly. Well laid out itinerary, very educational and also nice free time included. The wine tasting was amazing. It was beautiful winery , they served great lunch. Everything was outstanding. Highly recommended!
Sandy was great.
Andy T,
Aug 30, 2025
- Viator
5.00We had the best time on the Florence Day Trip: Chianti Wine Tasting, Siena, and San Gimignano tour! Sandy was terrific at explaining everything and made the whole day so much fun. She’s not only super knowledgeable, but also so lovely and easy to be around. The stops were beautiful, the wine was amazing, and having Sandy as our guide made the experience even better. Highly recommend this tour — and especially with Sandy!
Great tour
RuthEllen L,
Jun 9, 2025
- Viator
5.00Our guide, Elena, was warm, friendly, and engaging. I loved that we went first to San Gimignano before it got too crowded. Lunch at Fattoria Il Colombaio was wonderful. Be sure to buy a ticket to go inside the Duomo; it's magnificent! The vans were like new and very comfortable.
Great Tour
Sibby D,
May 28, 2025
- Viator
5.00Elena was our guide and she was wonderful!! She was very knowledgeable on our tour of Siena and San Gimignano. The winery was lovely and the food delicious. Sit up front in the van if you are prone to car sickness because the ride to and from Florence is a little frantic. But overall, I would highly recommend this tour.
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