We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Small Group Tuscany Day Trip From Florence with Chianti, Siena and San Gimignano

Select Date and Travellers
2 travellers
If you want to enjoy the best of Tuscany’s culture, food and history without the hassle of trying to find your way around its beautiful but often confusing country roads, our Tuscany Day Trip From Florence with Chianti, Siena and San Gimignano is the perfect trip for you. All you have to do is indulge your senses with wine, food and medieval architecture that exists nowhere else in the world.
  • Travel in a comfortable, air-conditioned vehicle from Florence
  • A small-group tour makes for an intimate experience
  • Enjoy a traditional Tuscan lunch and wine pairings at a local vineyard
  • See Siena, the Chianti wine region, and San Gimignano all in one day
What to Expect
After meeting in the center of Florence, climb aboard your air-conditioned vehicle and make your way to the Tuscan countryside. On the way, pause at the Piazzale Michelangelo to take in views of Florence. Next, stop at the medieval town of Siena, a UNESCO World Heritage Site known for its beautifully preserved architecture. Learn about the Palio horse race that’s held here, and visit the opulently decorated Siena Cathedral. Continue on to the rolling hills of the Chianti wine region. Stop at a family-owned winery and farm for a tour of the vineyards and cellar, and then settle in for a freshly cooked Tuscan lunch with wine. Your final stop is the San Gimignano, a UNESCO-listed medieval town known for its soaring towers. Explore at your leisure before returning back to your vehicle for the ride back to Piazza della Repubblica in Florence, where the tour ends.
Show More
Important Information
Departure Point
1: Viale Giacomo Matteotti, Firenze FI, Italy
2: Caffè Lietta, Piazza della Libertà, 6/7/8 Rosso, 50129 Firenze FI, Italy
Departure Time
8:30 AM
Return Details
Piazza della Libertà, Firenze FI, Italy
  • Expert, English-speaking tour Leader throughout
  • Lunch and wine tasting in Chianti
  • Comfortable, air-conditioned transport
  • Professional driver (separate to Tour Leader)
  • Small groups of only 18 people or fewer
  • Entry/Admission - Duomo di Siena
  • Gratuities
  • Hotel Pick-Up/Drop-Off
Show More
Additional Info
  • Confirmation will be received at time of booking
  • Please note that the cathedral of Sienna is closed on Sundays during visiting time and subject to closure during special celebrations/festivities, including the Easter ceremonies. If this occurs during your visit, the alternative itinerary includes an explanation of the cathedral from the outside. The supplier is unable to provide refunds or discounts.
  • This tour includes a full lunch. If you have any dietary requirements please contact us before booking and we will do everything we can to accommodate you
  • Unfortunately there are no accommodations for guests with mobility impairments, wheelchairs or strollers on this tour.
  • The order of the sites visited may vary.
  • Tour is in English only
  • Please remember that the Cathedral is a holy place and attire must be appropriate for the visit. Both men and women are asked to wear clothing that covers at least the shoulders and knees. Walks cannot be held responsible for denied entry due to improper dress.
  • Not wheelchair accessible
  • Near public transportation
  • Infant seats available
  • Most travelers can participate
  • This tour/activity will have a maximum of 15 travelers
Cancellation Policy
For a full refund, cancel at least 24 hours in advance of the start date of the experience.
Reviews (99)
Filter reviews
60 results
Traveller rating
Traveller type
Time of year
Traveller rating
Show reviews that mention
All reviews lunch and wine tasting san gimignano parking location italy tour smaller towns gelato final stop delicious lunch wonderful guide walking tour amazing trip highly recommend this trip interesting facts piazzale michelangelo great wine great job highlight of our trip
Selected filters
Updating list...
1 - 5 of 60 reviews
Reviewed 2 days ago via mobile

Comfortable bus and am informative tour guide. About 1.4 hours in San Gimignano (which is enough) and then a winery tour at Guardasteela; a gem of a boutique winery. We tasted 3 of their wines, plus a dessert wine - all paired with delicious foods,...More

Date of experience: September 2019
Thank 195davido
Reviewed 3 days ago

Every part of the day was excellent—the choice of cities, the lunch at a winery, the tour guide and the driver. It was also great to be n such a small group.

Date of experience: September 2019
Thank fippi
Reviewed 5 days ago via mobile

Antonio was a great guide, we were very lucky to have him. He was very knowledgeable and friendly. He did a great job making sure my gluten allergy was catered to.

Date of experience: September 2019
Thank Eric R
Reviewed 14 August 2019

The day is packed with so many stops, but our guide was knowledgeable, patient and kept us entertained. We enjoyed lunch and wines at a Chianti winery we visited. However, when the wine we ordered finally has arrived to the States, it was undrinkable. They...More

Date of experience: September 2018
Thank EP_SFran14
Reviewed 7 August 2019

The trip was one of the best we have attended. There were only 7 travelling in our bus - the group was split in half- so that made the experience relaxing and informative. The sights were beautiful, the food was tasty and the guide was...More

Date of experience: August 2019
Thank magson
View more reviews
Questions & Answers
Ask a question
5 August 2019|
AnswerShow all 3 answers
Response from ferrara10101 | Reviewed this property |
They did ask us if any one had any food allergies, no one did so I don’t know what the substitute would be. The lunch started with bruschetta and prosciutto, than ravioli and than a pork dish with salad. It ended with... More
24 May 2019|
Response from NH2CA | Reviewed this property |
It's a good amount of time in each place. The guide gives plenty of free time in each place. In my review, it says time to wander, time to get gelato, time by ourselves. There is plenty of time with and without the group.
Key Details
Why Book on TripAdvisor?
  • Low Price Guarantee
  • Free Cancellation up to 24 hours in advance
  • Secure Payments
  • 24/7 SupportCall: +852 30184991