Tuscany Day Trip: Chianti, Siena & San Gimignano

Embark on a gourmet adventure in the picturesque Tuscan countryside on a day trip from Florence. Explore the medieval town of Siena, savor a delicious lunch and wine tastings at a family-run farm in Chianti, and wander the enchanting streets of San Gimignano. Limited group size ensures a personalized experience.

Duration: 9 hours
Cancellation: 24 hours
Highlights
  • Tuscany - The tour begins with your driver and tour leader picking you up in a comfortable, air-conditioned vehicle in central Florence. You’ll be driven through the picturesque hills of Tuscany, passing by the best panoramic viewpoint of Florence, where you’ll stop to take some photos.
  • San Gimignano - Let your imagination run wild with a…
What's Included
  • Expert English-speaking tour leader
  • Free time in San Gimignano and Siena
  • Designated professional driver
  • Gourmet lunch and wine tasting in Chianti
  • Air-conditioned transport
What's Not Included
  • Gratuities
  • Hotel Pick-Up/Drop-Off
Additional Information

When in Florence, be sure to take a day trip to the picturesque and culinary haven of the Tuscan countryside. This small-group tour allows you to explore the charming streets of the UNESCO-listed village of San Gimignano. Delight in a seasonal lunch and wine tastings at a family-owned farm in the Chianti region, and explore the beautifully preserved…

Location
Piazza della Repubblica
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.
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
4.8
(267 Ratings)
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Mobile11909746518
Mar 15, 2026
Amazing Tuscany Day Trip with Francesca - I had an excellent day exploring Tuscany on this tour. Francesca was a fantastic guide—friendly, knowledgeable, and made the whole experience very enjoyable. We visited beautiful places including Siena and San Gimignano, and the Chianti wine tasting was a highlight. The scenery throughout the day was stunning and everything was well organized. Francesca shared great stories and information about the region which made the trip even more interesting. I highly recommend this tour if you want to experience the beauty of Tuscany in one day. It was a memorable experience and definitely one of the highlights of my trip.
Review provided by Tripadvisor
Navigate52979987587
Mar 12, 2026
Amazing experience! - Maria Cristina was excellent :) very knowledgeable and fun! Despite the weather the tour was great and the family owned winery the cherry on the cake, the wine so delicious! Recommended
Review provided by Tripadvisor
Fiona_w
Jan 3, 2026
Family trip into Tuscany. - We had the most fabulous day yesterday with my family of 7. From the drivers, the guide, the locations, the food, the wine and the timings. It was one if the best tours of our trip and I would highly recommend this company.,
Review provided by Viator
548x_
Dec 30, 2025
An Amazing Day Trip to Tuscany - Today we took the Florence day trip to Chianti, Siena, and San Gimignano, and overall the experience was excellent! Our guide, Antonio, was amazing!! Very knowledgeable, funny, and great at keeping the group engaged. He was also always happy to answer all of our questions throughout the tour. The highlight of the day was definitely the winery visit, where we enjoyed a delicious meal and sampled some wonderful wines, guided by Francesca, who was an outstanding sommelier and hostess. Finally, our driver Stefano was always punctual and provided a very smooth and comfortable ride. I would definitely recommend this experience.
Review provided by Tripadvisor
Daniel_t
Oct 23, 2025
End Game Day Trip - This 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 😉
Review provided by Viator
James_m
Oct 15, 2025
The perfect Tuscany experience! - 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
Review provided by Viator
Anisha_h
Oct 13, 2025
This was a fun tour.... - 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!
Review provided by Viator
Karen_f
Oct 13, 2025
Lovely personalized small group tour of Tuscany with delicious lunch! - 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'.
Review provided by Viator
J6241hlsusanf
Oct 12, 2025
Amazing tour of Tuscany: three gorgeous cities! - Excellent!! Thank you!! Amazing scenery!!! Loved everything about it!! Will book again in the future! Enjoyed the history and all the tour guides expertise!
Review provided by Tripadvisor
G9299nuamyc
Oct 5, 2025
Lovely - Lovely tour with 2 great Italian cities. Wonderful lunch at winery with great food and wine. Guide was excellent and very knowledgeable.
Review provided by Tripadvisor
From $225
up to 15 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).