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

“Way too much walking from bus to sites. San Gimignano was a waste of time. Long walk to the bathroom was it. Siena was wonderful one of the most beautiful cathedrals we have ever seen. The winery stop was great, the food was terrific and…”

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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

“We had a great time learning how to make 3 different types of pasta and tasting them with 3 different sauces! Our chef, Antonio, was kind and fun, he taught and guided us throughout the class. Great farewell experience in Florence! Perhaps some background music…”

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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 did the afternoon half day Chianti tour, we enjoyed the wineries, highly recommend, however I would not recommend the afternoon tour because it gets dark early and by the time you get to the 2nd location, it’s too dark to see the vineyards. I…”

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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

“We had a great guide. The two winery visits included just enough time to enjoy what they had to offer and company of the participants. There were only eleven of us!”

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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

“Our chef instructor, Narghess, was great. She was funny, friendly and very patient. Her English was exceptional and she knew many humorous American idioms. She kept us in stitches. She also was very generous with the libations during our pasta prep. After we made two…”

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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 was a fun experience. Tony was a great guide and gave us enough information but not too much. I would recommend for anyone looking for a nice way to spend an evening.”

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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

“I’ve now done this tour twice and both times were unforgettable. If you’re a food lover or just want to learn more about the Tuscan culinary culture, this tour is a must do. From start to finish the tour, struck the perfect balance between delicious…”

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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

“Visited lovely little villages and had free time to explore. Tour leader was friendly and helpful. Lunch was acceptable (appetiser was good, pasta main was average and no desert as promised, just a small biscuit). Wine was really nice but too expensive to buy. Overall…”

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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

“Wonderful experience of your, wine tasting, learning the history, and taking in the scenery. It was even a full moon night. Perfecto.”

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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

“Excellent, from customer service to every detail of the tour. The tour guide was professional and provided clear instructions.”

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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

“we made 2 pasta and a tiramisu. For me, I found the price to value not worth it given its vegetarian pasta. I was expecting meat sauce based. None of us had dietary requirements. There’s “unlimited” wine but its very cheap ones. It is still…”

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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

“It is a VERY big tour group - like 40-50 people (fills up a large tour bus), so it is quite hard to feel very engaged / involved. The winery tours were also quite high level, so I didn’t feel like I learnt a lot…”

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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

“A great way to see the Tuscan countryside with the wind in you face. Best thing I did from Florence to date. Tour guides were amazing and very knowledgeable of the Tuscan history. At the end you have lunch n plenty of wine in a…”

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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