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

“What a wonderful Tour! Our tour guide Mirella was great! We were very blessed to have her! She had a lot of knowledge about everything! I 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

“Such fun, the best thing we did as a family and skill for future. I took my two teenage daughters they loved it, the atmosphere was great shouting “yes chef” having a laugh. Loving the wine. Highly recommended and so cheap too!”

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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

“Anna was the perfect guide. The two wineries she took us to was expertly selected with one showing history and the whole process while the other was more homely and interactive. A definite recommend.”

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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

“Great experience. The drinks kept poring and this was genuinely the best tiramisu I have ever had. The guide was great, and even gives you a printout of the recipes to take home!”

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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

“Amazing day trip, with great guides sara & Gaia. Got to see pisa in daylight and night time. Food and wine lovey at the vineyard. Highly recommend”

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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

“This experience was exceptional in large part thanks to our tour guide Ado. The vineyards visited were truly stunning and looked out of movie, the wine was delicious and the dinner even more so! The entire group bonded over the food and how much fun…”

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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

“We took the Florence small group food and wine tour and had the most amazing time. Our guide, Antonella, was incredible! Knowledgeable, professional and funny, she provided the perfect blend of historical perspectives, cultural insights and several dashes of humor to make a wonderful experience…”

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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

“Ricardo, Alisandro and his team were fantastic. Ricky knew his stuff inside and out, was genuine, funny, engaging and very pleasant to be around all day. Alisandro was fantastic behind the wheel all day without a hiccup. Thanks for the fantastic day.”

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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

“This was an extremely interesting tours. Our guide and driver was exceptional attentive and helpful. Would highly recommend and want to do this tour again when I'm next in Tuscany. The wine, olive oil and balsamic we tasted as extremely good too!”

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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

“Really enjoyed the afternoon. Especially liked the first winery. Wine was delicious. Our guide Marta was wonderful. Bus was comfortable and not too much driving. Highly recommend!”

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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

“It was a great trip, I’m a vegetarian and the food was great. We brought our daughter who was 14 months and the tour was great for her.”

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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

“I highly recommend doing a cooking class. Our guide was engaging, funny and friendly and the whole experience allowed us to make new friends. The cooking class was one of the highlights of my whole trip.”

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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

“The guides did an expert job at explaining how to ride a Vespa and keep safe on the road. We all did a practice loop in the courtyard before going out onto the road. It was such a fabulous day riding through the beautiful Tuscan…”

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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