Tuscany Day Trip From Florence With Chianti, San Gimignano and Siena
9 hours
Max 14
Why take this tour?
Highlights
- Sit back and relax! Your two experts—a professional driver and tour leader—have all the logistics handled for a perfect day in Italy.
- Enjoy a farm-to-table lunch and Italian wine pairings at a family-run vineyard in Chianti.
- Spend free time in two of Italy’s most picturesque towns, Siena and San Gimignano.
- Travel aboard an air-conditioned minibus with a small group of no more than 14 people—a much more relaxing experience than the big bus tours.
- Sites Visited
- Piazzale Michelangelo
- Tuscany Region
- San Gimignano
- Chianti farmhouse & vineyard
- Siena
- Siena Cathedral (exterior)
- Tour Includes
- Gourmet lunch and wine tasting in Chianti
- Air-conditioned private transport
- Free time in San Gimignano & Siena
- Designated professional driver
- Expert English-speaking tour leader
Discover the best of Tuscany—Siena, San Gimignano & the Chianti wine region—on a perfectly planned day trip from Florence.
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Verified Customer reviews
Verified ratings
4.7 /5
based on 1520 Walks’ customer ratingsOverall rating
4.7 /5
1520 reviewsRating summary by category
Latest reviews
Excellent
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.,
Viator customer · Fiona · Jan 03, 2026 Excellent
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.<br /><br />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.<br /><br />I would definitely recommend this experience.
Tripadvisor customer · Xρήστος · Dec 30, 2025 Excellent
We had an amazing day trip from Milan to Siena, the Chianti wine region, and San Gimignano! Our guide, Stefano, and our driver, also Stefano, were both exceptional. Our guide was incredibly knowledgeable, explaining everything with clarity and great enthusiasm, and he was genuinely kind and attentive throughout the day. The transportation was very smooth and comfortable, and we always felt safe — thanks to our excellent driver. What made the experience even better was that it was a small-group tour with a minivan, which allowed us to enjoy the trip in a more relaxed and personal way. Siena was beautiful, the Chianti winery visit was a highlight with delicious wines, typical traditional lunch and stunning scenery, and San Gimignano was simply unforgettable. Overall, the trip was perfectly organized and truly exceeded our expectations. Highly recommended!
GetYourGuide customer · Nefeli · Nov 25, 2025 Great
Great guide, small group, and a fun experience. Wine and lunch were good, but I was expecting a lot more value for what I paid. There are similar tours that are half of the price that would probably be equivalent. Free time in the cities was a bit rushed. Was bummed that I spent almost $1k for a family of 4 for what we got.
GetYourGuide customer · GetYourGuide · Nov 07, 2025 Excellent
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 ��
Viator customer · Daniel · Oct 23, 2025
Reviews from our guests
Tuscany Day Trip From Florence With Chianti, San Gimignano and Siena
of Walks customers highly recommend this tour to friends or family Source: Walks Customers' Post-Tour Net Promoter Score Survey
Verified rating
4.7 /5
based on 1520 Walks’ customer ratingsTotal guest reviews
:
1731
guest reviews
Excellent 1391
Great 250
Good 65
Average 17
Poor 8
Latest reviews
Excellent
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.,
Viator customer · Fiona · Jan 03, 2026 Excellent
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.<br /><br />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.<br /><br />I would definitely recommend this experience.
Tripadvisor customer · Xρήστος · Dec 30, 2025 Excellent
We had an amazing day trip from Milan to Siena, the Chianti wine region, and San Gimignano! Our guide, Stefano, and our driver, also Stefano, were both exceptional. Our guide was incredibly knowledgeable, explaining everything with clarity and great enthusiasm, and he was genuinely kind and attentive throughout the day. The transportation was very smooth and comfortable, and we always felt safe — thanks to our excellent driver. What made the experience even better was that it was a small-group tour with a minivan, which allowed us to enjoy the trip in a more relaxed and personal way. Siena was beautiful, the Chianti winery visit was a highlight with delicious wines, typical traditional lunch and stunning scenery, and San Gimignano was simply unforgettable. Overall, the trip was perfectly organized and truly exceeded our expectations. Highly recommended!
GetYourGuide customer · Nefeli · Nov 25, 2025 Great
Great guide, small group, and a fun experience. Wine and lunch were good, but I was expecting a lot more value for what I paid. There are similar tours that are half of the price that would probably be equivalent. Free time in the cities was a bit rushed. Was bummed that I spent almost $1k for a family of 4 for what we got.
GetYourGuide customer · GetYourGuide · Nov 07, 2025 Excellent
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 ��
Viator customer · Daniel · Oct 23, 2025 Excellent
This tour was excellent! The time allotted at each place with the tour guide (Giada) along with the independent explore time was just right. She was full of excitement for and knowledge of all locations and encouraged our questions. The tour was balanced nicely with the lunch and wine pairing in between. The transportation was fantastic in a clean and roomy Mercedes van. I would highly recommend this tour. We loved it!
Verified · Lisa · USA · Female · 55 - 64 years · Oct 19, 2025 Excellent
Our quite Annette and driver were great . Really enjoyed the day and our lunch was wine tasting was so delicious and our host was very knowledgeable and passionate about her wines ! Bring in a small group was enjoyable . Recommend this.
GetYourGuide customer · Australia · Oct 16, 2025 Excellent
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
Viator customer · James · Oct 15, 2025 Excellent
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!
Viator customer · Anisha · Oct 13, 2025 Excellent
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'.
Viator customer · Karen · Oct 13, 2025FAQs
Is this tour wheelchair accessible?
No. Unfortunately, due to site restrictions we cannot accommodate wheelchairs on this tour. Guests should be prepared for a moderate level of physical activity, including standing for extended periods and climbing stairs, which may not be suitable for travelers with certain health conditions or mobility limitations.
Can I take this tour if I use a wheelchair?
Unfortunately, our vehicles cannot accommodate wheelchairs and some of the sights, like the farm, are not wheelchair accessible.
What if the weather is bad (rain, snow, hail, etc.) on the day of my tour?
Our tours run rain or shine so please dress for the elements. We also ask you to please remember hats and sunscreen if you are taking this tour in the summer as it might be very hot.
Does this tour accommodate vegetarians & people with food allergies?
Yes, but please contact our customer service team after you book ([email protected]) so that your guide will be aware on the day of the tour. Also, not all of the tastings on the tour can be substituted for others, but we will do our very best to make sure that you always have something to eat.
Can I bring my child's stroller on this tour?
Although the places we visit on this tour accomodate strollers we don't always have enough room in our transport vans to accomodate them. Please notify us after booking if you are traveling with an infant. Also contact us after booking if you require a car seat.
Does this tour include lunch?
Yes! Please email us beforehand and let us know if you have any dietary restrictions or food allergies.
Does this tour go inside the Cathedral of Siena?
Tickets for inside the Cathedral are not included on this tour, however you will receive an introduction to the cathedral from outside. Your guide can assist in buying tickets if you wish to go inside the cathedral.
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