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 a wonderful day visiting Siena, San Gimignano and Pisa. Excellent meal at the winery with plenty of food and wine. Our guide, Alessandro was excellent! Highly recommend the experience.”

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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

“We absolutely loved this trip! It was the best. It was a pretty big day and by the end of it youre definitely tired but its awesome. We were able to see so many places, whilst having an opportunity to rest in between each town.…”

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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

“Serious wine and great authentic dishes I have never tried before with a fun host. This was a great food tour with a local who gave a lot of info about the culture. Did I mention the wine? Perfecto!”

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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

“A great way to visit some of Tuscany. Takes a day but well worth the time. Dani , Sharon and Placido were outstanding guides. Thankyou”

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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

“The wine tastings were fantastic. Wine was absolutely delicious and more food than I expected at the first winery. Gorgeous scenery the whole way. Had such a blast”

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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

“This is probably my favorite excursion I’ve ever done anywhere in the world. The guides were amazing and the impeccable way it was planned enabled us to see an experience so much in a 12 hour. Period. Breathtaking views, amazing food, and a once in…”

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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

“Amazing cooking class with Tonya. Excellent step by step and so much fun!! Tiramisu was amazing and had fun learning how to make pasta from scratch.”

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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 was a nice trip! The tour guide lady explained everything well, think her her is Laurence. The two farms were nice. The first tasting we were too many for the room, suggest to give it a more personal touch. The views were spectacular. We…”

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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