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

“It was a great tour. Guide Alexandrio was very interesting and educational. Sites visited were very picturesque. Getting to try the best gelato in the world also helped”

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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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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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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

“What a great day! Sienna cathedral is stunning - a must visit. The wine pairing was very entertaining and good fun and the meal was tasty. San Gimignano was beautiful and I would really recommend going up the tower for some stunning views. The leaning…”

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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

“Guide was informative and fun. The wines were good as was the food served. The grounds and estate were lovely. Met lovely people from across the world and had great conversations. Only adults on this tour but they were of all ages. Highly recommend”

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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

“Eli was fantastic. She guided us on a wonderful food and wine journey through Florence. Her knowledge and passion elevated the experience providing unique insights and history. Highly recommend!”

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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

“Beautiful towns, gorgeous food and lovely hosts! The tour started on time and it was well organised. The bus was very comfortable with free wifi and plugs for you to charge your phones. Our hosts were very accommodating and attentive to our needs. Many thanks…”

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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 was amazing!!! We loved our tour guide Aaron. The wine venues were amazing. Would definitely go again”

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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

“Whilst this is a long day, it was worth it to see all the sights we saw! Our favourite stop was Siena, we would have loved to spend more time there. Lunch at Sam Gimignano was really nice. Our guide at Siena was quite difficult…”

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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

“Loved the one on one attention we received. The class was wonderful! We learned a lot about how to make pasta and tiramisu in addition to the history of Italian cuisine. My husband was hesitant about cooking but couldn’t stop talking about how wonderful everything…”

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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

“Had a great time at both Vineyards. Traveled with family and we had a great time seeing the Italian countryside together. Learned a lot about wine!”

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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 Vespa tour through Chianti was such a fun and unique way to see the region. Francesca and Wo were excellent guides—informative, helpful, and friendly. The lunch was delicious and the wine tasting very enjoyable. Highly recommend!”

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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