Florence to Tuscany: Iconic Chianti, Siena & San Gimignano Escape
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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.
Reviews
Reviews and Rating (Tripadvisor)
5 stars
4 stars
Reviews by Tripadvisor travelers
James_M, 10/15/2025 12:21:45 PM
Absolutely Spectacular! The guide was excellent, extremely knowledgeable. Transportation was perfect. Small vans dropped off and picked up right in the heart of all locations. Minimal walking to vehicles was a plus. The highlight of the trip, other than the wonderful cities was the lunch and wine tasting. Lunch was delicious and the wines complimented nicely. A very beautiful winery with a very vibrant host. I am so glad we chose this trip. I would highly recommend. 5 stars plus
Anisha_H, 10/13/2025 8:13:49 PM
This was a fun tour. Antonio was knowledgable, fun, and personable. I loved the two towns we went to, and I loved the stop right outside Florence for the views. The wine tasting and tour was also incredible - they made an effort to accommodate me as a vegetarian, which I also appreciate!
Karen_F, 10/13/2025 3:09:26 AM
A really nice tour and Jessica (our guide) was lovely, providing a lot of historical detail and answering questions along the way. Small group (only 6 in our van) was really the ideal way to see Tuscany. We bought the 'skip the line tickets' (10euro pp) to enter the Siena Cathedral through Jessica but I dont recommend this unless your really love cathedrals and do the homework ahead of time so you will actually understand what you are looking at in this large cathedral (mostly marble floor frescoes). IT will be crowded! The meal at the Poggio amorelli winery was delicious and the wine experience very nice! Giovanni, our driver, kept us safe and got us back quickly despite lots of traffic. Highly recommend if you want a more personalized experience vs the large "bus tours'.
J6241HLsusanf, 10/12/2025 10:26:56 AM
Excellent!! Thank you!! Amazing scenery!!! Loved everything about it!! Will book again in the future! Enjoyed the history and all the tour guides expertise!
G9299NUamyc, 10/5/2025 10:32:50 AM
Lovely tour with 2 great Italian cities. Wonderful lunch at winery with great food and wine. Guide was excellent and very knowledgeable.
Joseph_G, 9/27/2025 3:05:18 PM
Tour guide Jessica and driver Gabriel were very nice Jessica was very informative Lunch was wonderful
Fran D, 9/26/2025 12:33:01 PM
Our family had a wonderful time on our trip to Sienna, Chianti and San Gimignano. Our tour guide, Jessica, was superb — fun, friendly and extremely knowledgeable. Our lunch was delicious with generous glasses of wine poured. I highly recommend this experience.
O1845AGchristianv, 9/26/2025 11:33:05 AM
This was a great tour! They accommodated my dietary restriction and it felt like time flew by in Siena and San Gimianno. Would recommend Jessica again!
Robert_M, 9/24/2025 11:46:59 AM
Perfect agenda Small groups Knowledgeable and congenial guide Great driver Wine tasting was wonderful, so much fun and great food
Andra_B, 9/23/2025 11:51:28 AM
What a magical day! Antonio was the best guide…funny, knowledgeable and passionate. We were in a small group of 10, split across 2 luxury vans making it easy at every stop. The visit for lunch and wine pairings at the stunning Fattoria Il Colombaio was something very special, not to mention delicious. Marco and his family are winning at life. I HIGHLY RECOMMEND this tour and our guide.
- 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.
Departure point
Please arrive 15 minutes prior to the start of your tour, your guide will be holding a green Walks sign. This tour meets by the Carousel in Piazza della Repubblica.Return details
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.Redemption
- Please arrive 15 minutes before your tour start time for check-in. Out of courtesy to other guests, we’re unable to wait for latecomers. No refunds can be provided for late arrivals or no-shows. - Those with dietary restrictions or food allergies need to email our Guest Experience team at info@takewalks.com after booking the tour so we can arrange your lunch. - If you are traveling with a small child, please contact us. We need to confirm space on the vehicle for them. - Luggage and/or strollers are not allowed on this tour as there is no extra storage space on the vehicle. - 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. - 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. Please note that due to the religious nature of Siena cathedral, all individuals regardless of gender must cover their shoulders and knees. A scarf or shawl is acceptable. Walks cannot be held responsible for those denied entry. - Tips/gratuities (for your guide) are always appreciated. - Walks and Devour comply with all local government regulations. Please refer to local government guidelines for the most up to date information.24 hours before travel date - 100% refund
Less than 24 hours before travel date - 0% refund