Florence

15 Best Chianti Wine Tours

The Chianti tastings worth the drive: cellar visits at estates the same families have run for centuries, with cypress-lined roads doing the scenery between pours.

1.Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery

Explore Tuscany in a single day with visits to Siena, San Gimignano, Pisa, and a vineyard lunch—guided, scenic, and full of authentic Italian charm.

Most Popular★ 5.0

“enjoyed the tour tremendously, Sara our guide and Emilio our driver did a fantastic job. This tour was like a tasting menu of places in Tuscany. We really enjoyed the tour, the only downside was the rain which no one has control over. We had…”

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2.Florence: Pasta Cooking Class with Unlimited Wine

Discover the joy of making authentic Italian pasta inside a medieval Florence tower. Enjoy unlimited wine and learn from passionate chefs in a memorable cultural experience.

★ 4.9

“Fantastic ! Could not recommend enough. It’s fun, lively and really interesting. Super hands on the whole time - a really life way to dive into the food of Florence !”

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3.Florence: Chianti Wineries Tour with Wine Tasting

Experience Tuscany's charm on this half-day Chianti winery tour from Florence, with visits to two authentic vineyards, tastings, and scenic views.

★ 4.5

“We had the Chianti winery’s tour its was awesome it’s very romantic and really good value of the money if you’re suggesting or thoughts to do this trip don’t think that hard and enjoy yourself in Tuscany region !”

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4.Small-Group Wine Tasting Experience in the Tuscan Countryside

Discover Tuscany’s wines on a small-group tour from Florence, visiting two top Chianti wineries with expert guides, tastings, and stunning scenery.

★ 5.0

“The winery’s were absolutely beautiful and we couldn’t have asked for a better tour guide in Jonathan. He was so lively, informative, and personable with our group. We had a lot of fun!”

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5.Florence: Pasta & Tiramisu Cooking Class with Unlimited Wine

Discover Florence’s culinary secrets with this pasta and tiramisu cooking class, including unlimited wine, in a lively city-center restaurant.

★ 4.9

“This class with Amber was really great. She was immediately engaging and funny. Our small group all enjoyed music, wine, and a lot of laughs and learning. Amber taught us how to make pasta and tiramisu, gave us tips and recipes, and helped us to…”

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6.Pisa, Siena and San Gimignano Day Trip with Lunch & Wine Pairing

Explore Tuscany on a full-day trip from Florence, visiting Siena, San Gimignano, and Pisa, with optional lunch, wine tasting, and free time in charming towns.

★ 4.5

“You get a great overview of many places in a single day. There is not a lot of time for in depth sightseeing but you get to many places. They pull it off flawlessly.”

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7.Wine Safaris: Off Road Tuscany Wine Tours and Lunch from Florence

Experience Tuscany’s best with off-road wine safaris from Florence, visiting historic vineyards, tasting top wines, and savoring authentic Tuscan cuisine.

★ 5.0

“We could not have had a better experience for our first tour of the Tuscan Wine Region. Our guide was friendly and knowledgeable. The vineyards and wineries were gorgeous. Lunch was amazing! I have zero complaints (except that it all had to end when they…”

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8.Florence Sunset Food & Wine Tour with Eating Europe

Experience Florence's culinary scene on a 3.5-hour sunset food and wine tour. Tasting local cheeses, wines, Negroni, pasta, and gelato with expert guides.

★ 5.0

“Serious wine and great authentic dishes I have never tried before with a fun host. This was a great food tour with a local who gave a lot of info about the culture. Did I mention the wine? Perfecto!”

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9.San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting

Discover Tuscany in a day with visits to San Gimignano, Siena, Monteriggioni, plus wine tasting and a delicious local lunch. Perfect for history lovers and wine enthusiasts.

★ 4.5

“Sandro was great as our guide for all our destinations today! Highly recommend and lucky to get him!”

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10.Chianti Wine Tour from Florence

Discover Tuscany’s best with this half-day Chianti wine tour from Florence, visiting two charming wineries, tasting premier wines, and soaking in scenic views.

★ 4.5

“Way to see the wine country! I’m driving through the terrorist landscape filled with cypress trees and villas was breathtaking! There are miles and miles and miles off vineyards. Our tour guide was versed in several languages, so everyone could understand her words. She was…”

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11.From Florence: Chianti Half-Day Afternoon Tour

Experience Tuscany’s famed Chianti region on a half-day tour from Florence, tasting wines, olive oils, and exploring charming villages in the Italian countryside.

★ 4.4

“The wine tastings were fantastic. Wine was absolutely delicious and more food than I expected at the first winery. Gorgeous scenery the whole way. Had such a blast”

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12.Tuscany: Day Trip to Pisa, Siena, San Gimignano, and Chianti

Explore Tuscany’s highlights in one day with visits to Pisa, Siena, San Gimignano, and Chianti. Enjoy guided tours, a traditional lunch, and wine tasting for a memorable experience.

★ 5.0

“The tour guide was great. The bus was old and none of the air vents worked on a warm day, very uncomfortable”

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13.Cooking Class in Florence Pasta & Tiramisu Making Unlimited Wine

Discover authentic Italian cooking in Florence with this lively pasta and tiramisu class, including unlimited wine and personalized touches.

★ 5.0

“This was one of the best experiences our family had during our trip. Alessandro was a great host and put everyone at ease. And the food was delicious.”

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14.Half day Chianti Vineyard Escape from Florence with Wine Tastings

Discover authentic Chianti wines on this half-day tour from Florence, featuring visits to two wineries, scenic countryside views, and regional tastings.

★ 4.5

“We had a fantastic half-day Chianti vineyard tour with our guide, Alex, and our driver, Constantino. Alex was super engaging — he personally checked in with each of us to see if we had any questions or needed recommendations for Florence, which was so thoughtful…”

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15.Explore Chianti on a Vespa: Tour, Guide & Lunch from Florence

Discover Tuscany’s charm riding a Vespa through Chianti’s scenic hills, with wine tastings, a farmhouse lunch, and expert guides for an authentic experience.

★ 5.0

“Amazing experience. Loved every minute! Clear instructions and thorough check of our ability to drive a Vespa before we departed. We spent more time driving our vespas throughout the Tuscan countryside, than I thought we would. So many “pinch me” moments! And then to top…”

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More Chianti Wine Tours

4.9Florence: Street Food Tour with Wine & Local Guide2.5 hours$44 4.9Florence: Premium Pizza & Gelato Preparation Class with Wine3 hours$62 5.0Tuscany Bike Tours Through the Chianti Hills with Wine Tasting6 hours (approx.)$145.12 5.0Essence of Chianti Small Group Tour with Lunch and Tastings from Florence8 hours (approx.)$180.19 4.5Full Day Tour to Val d’Orcia and Gladiator’s Fields with Wines11 hours 30 minutes (approx.)$94.57 4.4From Florence: Chianti Wine Tour with Tastings$62.63 5.0Tuscany Wine tour & San Gimignano from Florence7 hours (approx.)$229.77 4.3From Florence: Chianti Hills Wineries Tour with Tasting6 hours$1,166 5.0Chianti Wineries Tour with Tuscan Lunch and San Gimignano8 hours (approx.)$229.77 4.5San Gimignano, Siena and Chianti Small Group Wine Tour11 hours 30 minutes (approx.)$167.74 4.5From Florence: Chianti Wine Tour with Tasting5.5 hours$41 4.9Florence: Street Food Walking Tour with Wine2.5 hours$45 4.5From Florence: Chianti Hills Half-Day Tour with Wine Tasting5 hours$48 4.5Chianti Half Day Wine Tour from Florence5 hours 30 minutes (approx.)$42.24 5.0Self-Drive Vintage Fiat 500 Tour from Florence: Tuscan Wine Experience4 hours (approx.)$139.00 4.5Tuscany Experience: Pisa, Siena, San Gimignano & Wine Tasting11 hours 30 minutes (approx.)$53.33 4.5From Florence: Small-Group Tuscany Wine & Oil Tour with typical Tuscan Meal7 hours (approx.)$96.86 5.0Tuscany Vespa Tour: Lunch & Wine Tasting, Countryside Roads5 hours (approx.)$228.62 5.0Tuscany Vespa Tours Through the Hills of Chianti6 hours (approx.)$193.49 4.9Florence: Tiramisu & Pasta Making Class with Unlimited Wine2 - 3 hours$53 5.0Horseback Ride in S.Gimignano with Tuscan Lunch Chianti Tasting8 hours (approx.)$229.77 5.0Cooking Art Brunelleschi with Unlimited Wine3 hours (approx.)$35.07 5.0Florence Foodie Tour: Discover the Best of Tuscan Cuisine & Wine2 hours 30 minutes (approx.)$92.54 5.0Tuscany Vespa Tour from Florence with Wine Tasting7 to 8 hours (approx.)$241.86