Recently Viewed
Chianti and San Gimignano Winery Tour: Unforgettable Wine Tasting and Food Pairing Experience
4.9
66 Ratings
Monteriggioni
Embark on an unforgettable wine tasting and food pairing experience in Chianti and San Gimignano. Visit charming wineries, explore beautiful villages, and indulge in the best of Tuscan cuisine. Book now!
Embark on an unforgettable wine tasting and food pairing experience in Chianti and San Gimignano. Visit charming wineries, explore beautiful villages, and indulge in the best of Tuscan cuisine. Book now!
Duration:
8 hours
Cancellation:
24 hours
Highlights
- Monteriggioni - Visit a first Chianti Classico Winery near Monteriggioni, one of the oldest and more famous in the region
- Chianti Road - Enjoy the ride with our English Speaking drive-guide who will tell you more about the territory and wines!
- Historic Centre of San Gimignano - Stroll around San Gimignano, the “gem” of the area, a…
- Monteriggioni - Visit a first Chianti Classico Winery near Monteriggioni, one of the oldest and more famous in the region
- Chianti Road - Enjoy the ride with our English Speaking drive-guide who will tell you more about the territory and wines!
- Historic Centre of San Gimignano - Stroll around San Gimignano, the “gem” of the area, a beautiful town like it was seven centuries ago.. and.. why not .. have a gelato before we go to the next winery!
- San Gimignano - Enjoy a special lunch with wine pairing in a winery in San Gimignano. Here you will taste also white wines such as Vernaccia, Sparkling Sangiovese and Vin Santo.
What's Included
- Hotel pickup and drop-off
- Wine-paired lunch in Chianti Winery
- Tours and tastings at two wineries
- Knowledgeable English-speaking driver-guide
- Comfortable in-vehicle air conditioning
- Complimentary bottled water
- Hotel pickup and drop-off
- Wine-paired lunch in Chianti Winery
- Tours and tastings at two wineries
- Knowledgeable English-speaking driver-guide
- Comfortable in-vehicle air conditioning
- Complimentary bottled water
What's Not Included
- Gratuities
- Gratuities
Additional Information
Our expert driver-guide will pick you up at your point of stay, ( No rally points, we come to you! ) embarking on a journey toward the core of Chianti Classico. Enjoy an exhilarating 1-day exploration in the pulse of Chianti and discover the most picturesque village in the locality.
Step 1 - Enchanting boutique winery in Chianti
Step 2 -…
Our expert driver-guide will pick you up at your point of stay, ( No rally points, we come to you! ) embarking on a journey toward the core of Chianti Classico. Enjoy an exhilarating 1-day exploration in the pulse of Chianti and discover the most picturesque village in the locality.
Step 1 - Enchanting boutique winery in Chianti
Step 2 - Exploration of Monteriggioni and/or San Gimignano
Step 3 - Culinary pairing for lunch at the most esteemed winery in the area
Duration of Tour: 7 to 8 hours.
Commencement Time: From Florence at 9:30 AM - From Siena at 10:00 AM
Note: During this expedition, you will be transported in a luxurious Mercedes 9 seat minivan that guarantees extreme comfort, with climate control, large scenic windows and plush seating.
Unless specific requests for privacy are made, it is possible that other individuals may join the tour ( maximum 1 van )
Fame: * (top-selling winery and culinary tour in Tuscany)
Location
Monteriggioni
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
(66 Ratings)
5 stars
4 stars
3 stars
2 stars
1 star
Mikiephillips
Sep 30, 2025
Great experience traveling with Tours of Tuscany! - We had 10 people and needed 2 vans. They took us to two amazing small wineries and then to small town for quick stop. They were very easy to set up trip and day of they suggested a change in one of our stops since we had already visited their suggestion and it worked out great for us all. Happy we choose this team!
Review provided by Tripadvisor
John_b
Sep 20, 2025
Unforgettable Day in Tuscany - What a wonderful and unforgettable day in Tuscany. Stefan picked us up near our hotel in Siena in his spacious, comfortable van and with two other couples set out on a day we will not soon, if ever forget.
Stefan knew all the back roads with all the amazing views as we set out to the first of two wine tastings. Then we were off to San Gimignano where we had plenty of time to enjoy that beautiful hill town.
Our final tasting and lunch outside in the Tuscan sunshine was just incredible. My wife and I have done a number of tours through Viator and this one ranks at the top. Cannot recommend too highly.
Review provided by Viator
Joshlz6457iu
Sep 8, 2025
Great tour, highly recommend! - Had a great time on the Chianti wine tour, Camilla took us to some great places and we had some amazing wine.
She was very friendly and professional ensuring we had plenty of time in each destination. Highly recommend this tour to anyone looking to see parts of Tuscany.
Review provided by Tripadvisor
Glen
Aug 3, 2025
First class through and through! - First class through and through. The tour is luxury as advertised. Personalized, well planned, and our guide and driver Camilla was amazing. She added so much to our experience. We learned about the history of the area, she managed timing of everything and kept us on track perfectly even with some extra time for conversations and extra wine tastings. Simply outstanding. You cannot go wrong with Tours of Tuscany and you would be missing out otherwise. Thank you Camilla, Silvia, and Niccolo! See you next time!
Review provided by Tripadvisor
A4378akmiguell
Jul 29, 2025
The Best Wine Tour !! - From beginning to end, this tour was completely amazing. Our first stop was at Casa Emma, where we encountered such a wonderful hostess who didn't just introduce us to the winery's passion for wine making, but taught us so much about the entire process as well. To make it even better, we were the sole couple on the property that morning, it really did feel as if we had the whole winery to ourselves!
Next, we stopped at San Gimignano, a small medieval town where we got gelato and went shopping in the local shops. Our final stop was a second winery, which we had an unforgettable lunch pairing at. Every course was paired nicely with the wines, and it was such a great dining experience.
What made this tour so wonderful, however, was our guide, Vincenzo. His knowledge, and enthusiasm, surpassed our expectations. He did not merely lead a tour, he created an experience. We enjoyed his tour so much so much that we are already planning our next visit just to have more time exploring Italy with him.
If you are considering doing this tour, don't hesitate, it's one you'll never forget!
Review provided by Tripadvisor
K3806ngmelissam
Jul 10, 2025
Perfect Wine Tour Experience for a Group in Italy - Here’s a short review you can use:
⸻
We had an incredible experience on our wine tour in Italy with our group of 17! The transportation was comfortable and air-conditioned—perfect for the summer heat. The hosts were warm, accommodating, and flexible with our schedule, which made the day feel relaxed and personalized. Each winery we visited offered something special, from beautiful views to delicious wines. A perfect way to experience Italy with friends! Highly recommend.
Review provided by Tripadvisor
J6701zuheatherr
Jul 8, 2025
Tuscany Wine Tour for our 30th wedding anniversary 😍 - This tour is absolutely perfect with the size, the agenda, the parings with the wine (delicious) the views (gorgeous) and the length.
Review provided by Tripadvisor
Northstar762169
Jun 30, 2025
Fun time in Tuscany - Amazing way to explore Tuscany! Our driver was very knowledgeable and a fun conversationalist. The first vineyard included a brief tour of their operations followed by an extensive tasting. It was delicious. San G is gorgeous. We tried the recommended ice cream spot- so good! Final stop was a lovely vineyard for a lunch and tasting. The lunch was four courses and so much food. The accompanying food wines were tasty. Happy we went this route- took all the guess work out of the logistics.
Review provided by Tripadvisor
Globetrotting667299
Jun 27, 2025
Chianti Tuscany Winery Tour, Siena City Tour with San Gimignano Winery - This company is absolutely fabulous!! We did a Chianti Tuscany tour with the entire family to two different wineries and it was fabulous. Stopped at the small town of Monteriggioni for some shopping and sightseeing in between. Camilla was our tour guide and she was so informative and we had a blast. She really made the experience perfect. We loved it so much that we booked another tour a few days later for just my partner and I. Camilla really out did herself. The tour started in Siena with a city tour and a private guide for the town then we went to the most amazing winery with the best lunch in San Gimignano followed by a walk around the walled town. Camilla was hands down the best tour guide we’ve ever had and not just in Italy but of anywhere we’ve been. Book with this company and you will not be disappointed! Ask for Camilla if you want the best experience of your life.
Review provided by Tripadvisor
Nicolecaci
Jun 16, 2025
Book with Camilla! - Camilla was a great guide for our family trip. She was very informative and kind, and organized a wonderful day of wine, sight seeing and fun! Book your next trip with Camilla!
Review provided by Tripadvisor
More activities from this operator
