Chianti and San Gimignano Winery Tour: Unforgettable Wine Tasting and Food Pairing Experience

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…
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
What's Not Included
  • 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 -…

Location
Monteriggioni
Cancellation Policy

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

Customer Ratings
4.9
(53 Ratings)
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Julesukgirl
Apr 29, 2025
Loved every minute... - An outstanding experience from start to finish. Our wonderful driver picked us up at our hotel in Siena and gave us a superb tour of the Tuscan countryside on the way to Il Columbaio- the first winery. After a great tour with the owner- the most charming and knowledgeable Nicola- we were seated in a gorgeous private room where Nicola talked us through tasting 6 wines- accompanied by great cheese and salami- superb day. You can stay here- we’ll be back and plan to do so- its so beautiful and scenic you feel like you are in a movie! We then went to San Gimigangno- where we had a couple of hours to wander- you can't park in the town so having a driver take you is really the only way to go. We were then driven to the second winery for more wine and a great lunch- a but busier but still beautiful- although much less attentive service than at Il Columbaio. The tour company- Tours of Tuscany- were just great throughout- would use them again in a second. They were keen to hear our feedback on both wineries and were just great at letting us customize the day as we went along
Review provided by Tripadvisor
Andreahu6655pa
Apr 16, 2025
A great day! - My family and I had an amazing day on the Chianti and san gimignano tour winery tour! Camilla picked us up at our villa even though it was out of the way! She was an incredible guide and she took us to the most amazing wineries! It was a great day!
Review provided by Tripadvisor
106kierann
Apr 10, 2025
Brilliant day - We booked this wine tour while traveling Italy for our honeymoon and it was brilliant! Camila was brilliant and both vine yards were amazing. Obviously the wine was brilliant as well. Well worth the month with lots of food and drink.
Review provided by Tripadvisor
Holly_a
Apr 4, 2025
Do not miss this! Perfect day. - My husband and I took this tour and it did not disappoint! We had the most amazing day. Stefan from Tours of Tuscany picked us up in a beautiful clean van with bottles Of water for us and we had a wonderful conversation until we got to our first destination, which was a beautiful private small winery. The scenery on the way was so spectacular and our tasting at the winery was amazing, we walked through the production process, strolled their gorgeous grounds and sat for a wonderful tasting and wound up ordering wine to be shipped to our home. The tour guide was very sweet and very knowledgeable, regrettably-I can’t remember her name. She even took the time to write down some suggested restaurants for us in Siena where we were staying. Then we got back into the van where we went to spend time in gorgeous San Gimignano. We walked around at our leisure and sat and had espresso, it was picture perfect and a must see place in Tuscany-it is like stepping back in time. Finally, we went to another winery which was a little larger and more well-known. The lunch we were served was absolutely delicious and plentiful! . Everything was set so elegantly Luca, our host, was engaging, extremely knowledgeable and passionate about the winery. We bought even more wine! We sat and ate, tasting, many wines and at no point during the tour did we feel rushed. Stefan patiently waited for us to enjoy our experience and then drove us back to our starting point. This will be a forever memory for us. Do not miss this experience. .
Review provided by Viator
Kingsportrunner
Nov 1, 2024
Great day in Chianti country! - “Billy” was a wonderful guide and driver! He reserved two fabulous Chianti tastings including a sumptuous lunch at the second. He was so patient with us when we got lost in San G…. 😳
Review provided by Tripadvisor
Tsav323
Oct 23, 2024
Wonderful Chianti Tour - Our private tour consisting of 6 adult family members could not have been more exceptional. Yes, weather conditions were poor… rain, but the vibrant smile and truly exuberant personality of our tour driver, Camila, set the tone for a wonderful day. The small winery was incredible and we recognized that with substantial purchases of their delicious products. San Gimignano was wet but oozing with history and provided memories that will last forever. While the final winery was less personal, the lunch meal was exciting and provided the basis for a needed nap on the ride back to Florence. I highly recommend this tour and can only hope all are able to have Camila has your guide.
Review provided by Tripadvisor
Mimosa428
Oct 23, 2024
Amazing Tuscan Tour of 2 Wineries with Tastings and Lunch and a Visit to San Gimgnanoo - A great day in Tuscany. Valerio picked us up at the cruise port and took us through the Tuscan countryside to a small family winery, Il Colombaio, and larger facility, Tenuta Torciano. Valerio was knowledgeable and had a great sense of humor. He hails from Livorno so knew the area very well. We enjoyed our tasting at Colombaio and were so impressed with the quality of wines and balsamic, that several of us ordered products to ship home. Tenuta was a larger facility where we enjoyed a Tuscan lunch and wine pairing. We thoroughly enjoyed the brief visit to San Gimignano and indulged in the famous gelato at Gelateria Dondoli!
Review provided by Tripadvisor
Jillhn4473lm
Oct 15, 2024
Amazing day spent in the Chianti area! - Amazing wines! So interesting and informative! Beautiful wineries! The lunch served was beyond fantastic! Highly recommend this excursion! Coming from California, and having access to great wines, we were absolutely blown away by the great wines we had the chance to taste!
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Sidney_l
Oct 12, 2024
Best experience, would recommend to anyone!!! - This was such a great experience to see the vineyards and taste the wine of Chianti. We absolutely love love loved our driver and tour guide who made our day completely amazing and special. Thank you to you, Camilla!!! She answered all of our questions about living here as a local, what her life is like, about Italian culture and language, and of course about the wineries and wines. She even helped us book a taxi for our next day transportation. She was FABULOUS!!!! The vineyard and winery we visited were very nice. The food was great, and the wine was better!! Visiting San Gimignano was also really cool to see and definitely worth the stop.
Review provided by Viator
Laurennd1433ua
Jan 4, 2025
Wonderful Experience! - My husband and I were staying a little outside of the city and Tours of Tuscany made it so easy for our wine trip! They picked us up right in front of our hotel and then we headed on our way to our first location. Our driver taught us about the history of the region and what was required to make Chianti vs other wines so we were well prepared for our tours at the wineries. Unfortunately, the driver made a wrong turn and we arrived 30 minutes late, so we missed the walk around the vineyard which was disappointing. However, we still enjoyed our small group tour; our second stop in the city of San Gimignano was great! We were able to stroll through the area, see wonderful views of wine country and shop. Then we headed to our second winery, a "fancier" and bigger operation than our first. We were treated with a drink while we waited for our lunch. Our meal was perfectly complimented with specific wine samples and they even made vegetarian meals for us! We had a wonderful time and I can't wait to return to Tuscany to book another tour with Tours of Tuscany.
Review provided by Tripadvisor
From $281
up to 8 guests
2 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).