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

“We had so much fun! Alex and Sergio were amazing. The fun facts throughout the tour from Alex were informative. I fell in love with Italy even more than I already have. Definitely recommend this tour.”

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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

“The Chef was amazing as he had kept the entire group engaged during the entire class. He came to everyone personally and suggested Tips on how to improve their pastas. In totality we were served 3-4 Pasta items that the group had prepared. Free wine…”

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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

“This was a highlight of our Florence trip. Our guide was fun and the wines were great. Visiting 2 vineyards was amazing and we tried 7 wines. Would highly recommend this trip.”

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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

“So fun!! Our guide Jonathan was wonderful! The hosts at each vineyard were delightful and the whole experience was one of our favorites in Florence- plus I have a new appreciation for Chianti! Highly recommend it! Our bus was Americans, Australians, Russians and Brazilians and…”

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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

“Jacoppo our guide was excellent in timing every location. He is organized. We were able to reach pisa with plenty of daylight.”

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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

“Ginevra created the most amazing day for us! Perfect amount of narrative mixed with allowing us to enjoy independently. The winery and lunch were spectacular. Sergio was also an amazing driver. Cannot wait to return to take this tour again!!”

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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

“Food tours are a great way to see a city the first day you are there. We really enjoyed the tour and our tour guide was excellent. We absolutely would recommend this tour — the 4 star rating is really to differentiate it from other…”

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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

“Awesome experience from being to end! The winery was wonderful and Cristiana or Catiana not sure about spelling was informative, kind and very friendly!”

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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

“Lucano and Francesco were amazing hosts for this wonderful Chianti region and winery tours. So beautiful, romantic and of course delicious wines. Definitely recommend to others, get the balsamic vinegar and truffle olive oils with the wines.”

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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

“What a fun day! We saw so much and learned a great deal. He made sure he got his to Pisa early so that we could beat the crowds, and that was a very good thing. The wine tasting and food were phenomenal. Every step…”

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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

“Great experience and fantastic food. Jacob was engaging with everyone and kept the kids entertained. We Would definitely do it again.”

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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

“Overalll, the guide and bus driver were very nice and informative. Wine tasting was ok- vineyards were good to see. This tour should consider changing the start time- 2nd vineyard was beautiful place but you could not see because of time of day- dark. Had…”

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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

“Great experience! Definitely worth it! Our guides were Chiara and Carlotta and they were awesome. Tour starts with 30 minutes bus ride to Vespa location where you practice riding. Guides were very helpful. The ride on the Vespas was around 1.5 hours through the country…”

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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