Recently Viewed
Tuscan Wine Tour: Chianti Tasting and San Gimignano
4.9
208 Ratings
Firenze
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!
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 - The journey begins at 8:00 from the pick-up location, followed by a 15-minute drive to Piazzale Michelangelo. This spot offers a breathtaking panoramic view of Florence, allowing you to admire the city in all its splendor. The expansive square features a bronze replica of Michelangelo’s David.
- San Gimignano - At 8:30,…
- Piazzale Michelangelo - The journey begins at 8:00 from the pick-up location, followed by a 15-minute drive to Piazzale Michelangelo. This spot offers a breathtaking panoramic view of Florence, allowing you to admire the city in all its splendor. The expansive square features a bronze replica of Michelangelo’s David.
- San Gimignano - At 8:30, we embark on a 1-hour drive to San Gimignano. This enchanting walled city, rich in history and charm, is renowned for its towering structures and delectable ice cream, promising to tantalize your taste buds. You will have 1 hour and 25 minutes to explore.
- San Casciano in Val di Pesa - At 10:55, we head out for a 50-minute drive to a traditional Tuscan farmhouse in the Chianti region. Here, in the heart of Tuscan wine country, you will visit a picturesque farmhouse with a wine cellar. Enjoy a delightful Tuscan lunch featuring exquisite regional cuisine and some of Italy’s finest wines. This is a perfect chance to unwind and take in the breathtaking views of the Tuscan countryside. You will have 2 hours and 30 minutes to enjoy this experience.
- San Michele a Torri - At 14:30, we drive for 25 minutes to San Michele a Torri for a final stop at a family-operated wine estate in the Florence province. Here, you can sample more exceptional Chianti wines. To truly appreciate Chianti, one must try at least 5 or 6 different varieties from the region. You will have 45 minutes to savor this experience.
- Florence - At 15:50, we return with a 40-minute drive to the original pick-up point, arriving by 16:30. This ensures you have ample time to enjoy more of your Florentine afternoon.
What's Included
- WiFi on board
- Bottled water
- Wine tasting and olive oil tasting
- Air-conditioned vehicle
- 1 Bottle of Prosecco White Wine per group
- Lunch
- One unlimited Wi-Fi Pocket-Sized Hotspot for each couple. Stay connected throughout your journey.
- Alcoholic beverages
- WiFi on board
- Bottled water
- Wine tasting and olive oil tasting
- Air-conditioned vehicle
- 1 Bottle of Prosecco White Wine per group
- Lunch
- One unlimited Wi-Fi Pocket-Sized Hotspot for each couple. Stay connected throughout your journey.
- Alcoholic beverages
What's Not Included
- Gratuity
- 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…
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 landscape photography, this tour is perfect for you. Additionally, you will have the opportunity to visit San Gimignano, one of the world’s most beautiful villages, renowned for its stunning towers and delectable ice cream. Our tours exclusively use black, air-conditioned Mercedes Vans, equipped with air conditioning, WiFi, and a Pocket-Sized Hotspot with unlimited Wi-Fi for each couple, along with a bottle of water for every participant, and a bottle of Prosecco White Wine for a delightful happy hour at the tour’s conclusion!
- A maximum of 8 people per Mercedes van
- Direct pick up and drop off from some hotels locates in the historic center (A zone). For all other locations private residences and B&B the meeting points is: In front of Hotel Boccaccio-Tino Caffè, Via della Scala 59 (one minute walking distance from Santa Maria Novella train station), Florence at 8,00 am. Please arrive 15 minutes before scheduled departure time. If you wish you can have breakfast there, English or continental or just a “cappuccino”. As I Just Drive guests at Tino Caffè you are entitled to have a 10% discount.
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.
For a full refund, cancel at least 24 hours before the scheduled departure time.
Customer Ratings
4.9
(208 Ratings)
5 stars
4 stars
3 stars
2 stars
1 star
Lisari5213ty
Jun 5, 2026
Amazing days with Claudius! - We had an amazing time! Claudius was our amazing guide four different days! We saw Cinque Terra, Pisa, Lucca, Greve, II Molino Di Grace Winery, another winery, San Giomano, and Florence. At the end of our ten days we spent four with Claudius and he was a part of our family. Truly appreciate all he did! We have been back in the states for a few days and we still chat and reminisce about our days in Italy. He made us feel special - like celebrities! Love him for that.
Review provided by Tripadvisor
Global54504627354
Jun 5, 2026
Lovely day led by Nedo! - Nedo was the best! Loved his passion and engagement. San Gimignano was the best little stop and the winery visits and tasting were so lovely. Highly recommended.
Review provided by Tripadvisor
Craig
Jun 3, 2026
Claudius was our driver and he was exceptional. His knowledge of the region was second to none. Make sure you book tour - The tour itself was terrific and the wines and food were spectacular.
Review provided by Tripadvisor
Danast3128sk
May 28, 2026
Best Way to See Tuscany, Small Towns, and Wineries - Our tour with Gabriele was fantastic and a perfect way to spend our anniversary! While we booked the semi-private tour, no one else signed up for our tour and we had a private tour. The tour is planned perfectly so you attend Piazzale Michelangelo and San Gimignano in the morning before all the crowds and big tour buses come. Really made such a difference and beautiful impression on our time in these places. The small family wineries with tours and tastings were so personable and fantastic. The lunch was fabulous - a four course tasting menu! We appreciated the pick-up right in front of our hotel (Hotel Davanzati) and the booking discounts with the hotel and in cash payment. The whole team before and during the tour were so responsive within 24 hours any time we had questions; we had a personal situation before the trip where we had to switch back and forth between the two small group tour options (wine tasting and CinqueTerre) and the team was completely understanding and kind throughout. Thank you!
Review provided by Tripadvisor
Angelbrigman
May 27, 2026
Winery - Marco was wonderful! Very informative and great personality!
Review provided by Tripadvisor
Mynonnie
May 25, 2026
Day trip to San Gimignano and two wineries - The first stop on our trip was the Piazzale Michelangelo, which was quite a surprise. If you’re in Florence, it’s a must see/do. The views over the city are outstanding. The drive to the spot is quite beautiful as well. Then, our next stop was the quaint town of San Gimignano. We had about an hour or so there to wander on our own. We loved the town so much we could have stayed there all day. I was glad it was our first stop as the larger tour groups started coming in as we were leaving. So I recommend getting there early. Also, the line for the world famous gelato is also a lot shorter before the crowds start descending on the town. There are amazing views of the vineyards and there are many cute shops and restaurants to visit.
Our next stop was the first of two wineries. This one was the larger and, I guess more commercial, of the two. The second one was a family run business. I enjoyed our visit to the first winery more than the other. In fact, the one winery would have sufficed. It’s a lot of wine to drink in a day. The first winery was a combination of food and wine. Both the food and the wines were delicious. I’m not a wine lover mostly because of the way it makes me feel afterward, but as their wine is made without sulfates, you don’t experience the headaches and dehydration as you do with other wines. Of course, at the end of the demonstration and wine tasting, the sales pitch came. It wasn’t too bad though or too much pressure to buy anything. You can have their wines, olive oil, and balsamic vinegars sent to your home address without shipping fees. Their wines were very good, but the balsamic vinegar was really outstanding. Their olive oils were delicious as well. So for some, it might be worth it to purchase some of the items.
We weren’t at the second winery very long. A representative from the winery gave an explanation on how the wine is produced and then we had a wine tasting.
Overall, it was a great day. If I were to do it again, though, I would try to find a tour that stops at San Gimignano, a winery, and Siena. I would have preferred a visit to Siena over a visit to the smaller winery.
Marco, our guide and driver, was great - very kind and helpful. I would definitely book a tour with this group again.
Review provided by Tripadvisor
Dorispn202bg
May 24, 2026
Excellent San Gimignano & Chianti Wine Tour - I had such an amazing experience on the San Gimignano and Chianti wine tour. Everything was very well organized and the scenery throughout the day was absolutely beautiful. The wine tastings were excellent and San Gimignano was definitely a highlight of the trip. A special thank you to Andrea, our driver, who was incredibly kind, professional, safe, and knowledgeable. He shared so much interesting information about the region and made the entire experience smooth and enjoyable. I would definitely book again and highly recommend this tour too everyone!
Review provided by Tripadvisor
Gabbylasala
May 21, 2026
Great use of a day in Florence/Tuscany vineyards - Andrea was great! We spent 2 hours in San Gimignano and then spent the rest of the day driving through the country side and vineyards. Both wineries were great and our food was fantastic. Would do again!
Review provided by Tripadvisor
Marcusdelaney822018
Apr 21, 2026
Great day out - We had an absolutely fantastic experience exploring Tuscany with Andrea from TrueScany. From the moment we were picked up, it was clear we were in great hands. Andrea is not only an incredibly professional driver, but also genuinely friendly and welcoming, which made the whole day feel relaxed and enjoyable.
What really set this trip apart was Andrea’s deep knowledge of the region. He shared fascinating insights about the history, culture, and hidden gems of Tuscany that we never would have discovered on our own. Every stop felt thoughtfully chosen and perfectly timed.
The vehicle was spotless and comfortable, and Andrea’s driving was smooth and safe throughout—something we really appreciated on the winding Tuscan roads. He went above and beyond to make sure we were comfortable and getting the most out of our experience.
If you’re looking for a personalized, informative, and truly memorable way to explore Tuscany, we can’t recommend Andrea and TrueScany highly enough. It was one of the highlights of our trip! Thanks again, Andrea from Marcus and Alex, the Australian / German couple
Review provided by Tripadvisor
Lyanne
Jun 2, 2026
Almost perfect - It was great! The only thing I was a tad disappointed with was that we did not have a lunch outdoors with the view and we never got to walk around with a glass of wine outside. The two wineries were great and wonderful at explaining everything they do. David, our driver was excellent! The food was amazing and the wine was fabulous!
Review provided by Tripadvisor
