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
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.
Please note that the private option does not include a guided tour of San Gimignano. Guests will instead enjoy extended free time to explore the town at their own pace.
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 (valid only for the group tour))
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: Enjoy a Siena guided tour, a gourmet lunch at a vineyard in Chianti, and free time to explore San Gimignano at your own pace.
Reviews
261 reviews
Total reviews and rating from Viator & Tripadvisor
End Game Day Trip
Daniel T,
Oct 23, 2025
- Review from Viator
5.00This trip was well worth the money! You get a great introduction to both Siena and San Gimignano, followed by free time to explore each city. The wine tasting and lunch was some of the best food/drinks we had on our trip in Italy. Our tour guide and driver were both friendly people and knew a lot about Italy, the region, and had great recommendations for Florence. Highly recommend this tour if you’re even slightly considering it. Just make sure you’re not hung over 😉
The perfect Tuscany experience!
James M,
Oct 15, 2025
- Review from Viator
5.00Absolutely 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
This was a fun tour....
Anisha H,
Oct 13, 2025
- Review from Viator
5.00This 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!
Lovely personalized small group tour of Tuscany with delicious lunch!
Karen F,
Oct 13, 2025
- Review from Viator
5.00A 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'.
Amazing tour of Tuscany: three gorgeous cities!
J6241HLsusanf,
Oct 12, 2025
- Review from Tripadvisor
5.00Excellent!! Thank you!! Amazing scenery!!! Loved everything about it!! Will book again in the future! Enjoyed the history and all the tour guides expertise!
Lovely
G9299NUamyc,
Oct 5, 2025
- Review from Tripadvisor
5.00Lovely tour with 2 great Italian cities. Wonderful lunch at winery with great food and wine. Guide was excellent and very knowledgeable.
Nice tour
Joseph G,
Sep 27, 2025
- Review from Viator
4.00Tour guide Jessica and driver Gabriel were very nice Jessica was very informative Lunch was wonderful
Superb day in Tuscany
Fran D,
Sep 26, 2025
- Review from Tripadvisor
5.00Our 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.
10/10
O1845AGchristianv,
Sep 26, 2025
- Review from Tripadvisor
5.00This 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!
Perfect day in Tuscany
Robert M,
Sep 24, 2025
- Review from Viator
5.00Perfect agenda Small groups Knowledgeable and congenial guide Great driver Wine tasting was wonderful, so much fun and great food
From €189.00
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