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

“Manolo and his team took great care of us and were so knowledgeable about all the places we went to. The sights were fabulous and the winery was absolutely exceptional! We had plenty of free time to explore, buy some souvenirs and make life long…”

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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

“This activity was a ton of fun and was actually the BEST pasta we ate our entire trip! Chef Victoria was funny and helped us make 3 different pastas. Wine was great too! Definitely recommend fitting this in your itinerary while in Florence.”

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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

“This was a dream come true day for me... My husband and twin 22 year old sons came along for the ride [they are not wine drinkers]. Our tour guide Matteo on the bus ride from Florence to the two vineyards we visited was a…”

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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

“We had a delightful experience in Clive’s cooking class with our family of four. It was a memorable day as we learned to make ravioli, tagliatelle, and tiramisu. Clive was incredibly patient with us, as we were complete beginners in cooking. He made the class…”

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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

“From the beginning it was very organized, easy to get to the meeting point. Constantino our tour guide was excellent, caring and very knowledgeable. We visited beautiful and charming towns to get beautiful pictures and buy souvenirs. Wine tasting and lunch was very good! Seat…”

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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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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

“This tour was well worth it. We enjoyed discovering the medieval towns inTuscany, lunch was tasty, bus was comfortable. The three staff assigned to our tour were Alexandra, Stella & Nino and they were all lovely & wonderful! Highly recommended tour!”

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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

“It’s was a quick trip out to the vineyards. The bus was comfortable but it was hot. You can ask the guide to cool it down though. The wineries were great, a-little short lived though. Some groups were disrespectful and talked while the winemakers were…”

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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

“Perfect trip when you only have 1 day to see numerous historic and beautiful places without the hassle of planning and logistics. They do it all so you can enjoy. Our guide Ricardo and our driver Stefano were professional, courteous and friendly. Thank you for…”

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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

“Ambar was great! She was so helpful and funny, which made the experience even better. The intimate group setting made it feel special, and we ended up making friends with another couple. Thanks to Ambar’s patience and great sarcasm, we made the best pasta and…”

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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’s a unique experience . Enjoyed it . Tks John for the lovely explanation and clear instruction The drive is very good too. It was a very smooth journey”

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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