Tuscan Wine Tour: Chianti Tasting and San Gimignano

Embark on a semi-private tour from Florence and indulge in the enchanting flavors of Tuscan Chianti wines. Immerse yourself in the picturesque landscapes while visiting two wineries and savoring a delectable lunch. Don’t miss the chance to explore the iconic village of San Gimignano and capture stunning photos. Join us for a wine-filled adventure with luxury amenities and a delightful champagne toast!

Duration: 8 hours, 30 minutes
Cancellation: 24 hours
Highlights
  • Piazzale Michelangelo - We start from the pick up point 8:00 and then drive for 15 minutes towards Piazzale Michelangelo. Piazzale Michelangelo offers a stunning panoramic view of Florence, where you can take in the city in all its glory. The large square is home to a replica of Michelangelo’s David in bronze.
  • San Gimignano - At 8:30 we’ll…
What's Included
  • Tasting of various Chianti wines
  • Complimentary iPad with mobile data per couple
  • On-board WiFi access
  • Bottled water included
  • Wine and olive oil tasting experience
  • Travel comfortably in an air-conditioned vehicle
  • Complimentary bottle of Prosecco White Wine for the group
  • Enjoy a delicious lunch
What's Not Included
  • Gratuity
Additional Information

This tour is crafted to fulfill your Tuscan wine-tasting aspirations. Experience the iconic, postcard-perfect landscapes of Tuscany as you journey from one winery to another. You will explore two wineries and have the chance to sample a selection of premium Tuscan Chianti wines. Lunch is provided. If you appreciate fine wine, exquisite cuisine, and…

Location
Hotel Boccaccio
Via della Scala
The tour starts at 8:00. Please show up at the meeting point 15 minutes in advance.
Cancellation Policy

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

Customer Ratings
4.9
(188 Ratings)
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Fitgirl2
Oct 2, 2025
An exceptional Tuscany tour experience - This tour was excellent and our tour driver, Claudia’s, was fantastic! We visited San Gimignano and two different vineyards in the Chianti region in Tuscany. The lunch at the first vineyard was excellent and the tour at the second vineyard (which was organic and also made olive oil) was the perfect finish to the day. Highly recommend!
Review provided by Tripadvisor
Carolanng654
Sep 20, 2025
Our favorite wine tour! - Sara was excellent as our guide and driver. The 4 stops were exactly what we wanted.... Scenic views, leisure time to walk the town, great winery tours and foods. Highly recommend this activity.
Review provided by Tripadvisor
Q4438zxcarolynj
Sep 9, 2025
Perfect day wine touring! - Diana was terrific! She gave us lot of information and history about the region. She was funny and fun to hang out with! Lots to do on this excursion.
Review provided by Tripadvisor
Melinda_f
Sep 6, 2025
Great Day Trip. - It was a great day trip. Our driver Francisco was awesome! Very knowledgeable of the Area, and personable. We had a four course lunch at the first winery. (That took a bit long for us) we learned at both wineries and the wine at both were great
Review provided by Viator
Amy_f
Sep 4, 2025
Excellent experience - All aspects of this excursion were enjoyable…the vineyards, the San Gimignano stop, and lots of delicious food and wine! Our driver was very friendly and knowledgeable, and we were grateful for the small group dynamic. Nice to have someone else do all the planning and driving. Vehicle was very comfortable.
Review provided by Viator
Kathryn_l
Aug 27, 2025
Great tour - Fantastic! Fantastic! If you’re going to do one tour in Florence make it this one. If you can book with Diana, we met at 8am and left with a friend in Italy at 5. Great food and wine and very knowledgeable about the area. I can’t recommend this trip enough just book it!
Review provided by Viator
818cydneym
Aug 7, 2025
Best of Exploration and Wine - Took this tour for my birthday and it was the best way to celebrate with family and friends. Sara was great and both wineries blew us away.
Review provided by Tripadvisor
Rosiemo8704bb
Aug 4, 2025
Great experience and driver! - Claudius was a great guide and provided history lessons on the way to our destinations. Everything was so wonderful, I’d definitely go again.
Review provided by Tripadvisor
Kathryn_d
Jul 29, 2025
My husband and I... - My husband and I absolutely loved this experience and would do it again in a heartbeat! Our driver Sara was lovely and such a pleasure to be around. Each location was allocated the perfect amount of time and it was a great way to escape Florence for the day. The trip to San Gimignano was the perfect amount of time to explore the local shops. Gelato Dondoli was recommended to us by Sara and it did not disappoint. Such unique flavors, truly some of the best gelato we had during our trip to Italy! We stopping in Le Tori a.r.l. for some leather shopping and it was a wonderful experience. The woman who helped us was knowledgeable and took the time to explain different aspects of the leather and craftsmanship to us. There are also some lovely linen clothing stores there as well. The entire experience at Castillo Monterinaldi was phenomenal. Andrea led us on the tour and wine tasting. The tour was lovely, Andrea was knowledgeable and answered any questions we had. The wine tasting was one of the best experiences. The food was unreal and the wine pairings were perfection. I also have a severe food allergy and they were extremely accommodating and understanding. The tour at the second vineyard was lovely. It was a smaller wine operation than the first vineyard. We were lead through an olive oil and wine tasting. The Chianti was paired with a beautiful selection of meats and cheeses from the farm. If we were staying in Italy longer I would have loved to have purchased some.
Review provided by Viator
Riley
Jul 4, 2025
10+/10 ⭐️ - Claudius was AMAZING! We booked the semi private tour from Florence. Claudius was knowledgeable and gave us so many good recommendations. The two wineries we visited were welcoming and delicious! Began as strangers and ended as friends!
Review provided by Tripadvisor
From $243
up to 8 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).