Florence

15 Best Chianti Wine Tours

Chianti tastings from Florence, narrowed to tours that visit real working estates. Chianti Classico is the strip of hills between Florence and Siena; look for the black rooster seal on the bottles. Half-day trips squeeze in two wineries, and autumn harvest dates book out first.

1.Tuscany Day Trip From Florence: Siena, San Gimignano, Pisa and Lunch at a Winery

Step into the past with a Tuscany day trip from Florence, exploring Siena, San Gimignano, Pisa, and more—unveiling Italy's hidden gems and culinary treasures.

Most Popular★ 5.0

“Great tour guide and it was a great way to see multiple sites in one day. We loved lunch at the vineyard!”

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2.Florence: Pasta Cooking Class with Unlimited Wine

Discover Florence’s culinary secrets with a pasta-making class inside a medieval tower, including unlimited wine and authentic recipes in just 3 hours.

★ 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.Florence: Pisa, Siena, San Gimignano, and Chianti Experience

Discover the best of Tuscany with a Florence adventure! Explore Pisa, Siena, San Gimignano, and Chianti, and indulge in the beauty of Italy's iconic cities and rolling vineyards.

★ 4.5

“I enjoyed every moment of this tour. Barbara is an amazing guide and told us everything about the places we visited and where to find the best gelato and coffee (and bathrooms😅). For the Siena tour, Chiara was an amazing tour guide and the lunch…”

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6.Small-Group Wine Tasting Experience in the Tuscan Countryside

Kissed by the Tuscan sun, a small group embarks on a sensory journey through vineyards, uncovering the essence of this famed winemaking region.

★ 5.0

“The winery’s were absolutely beautiful and we couldn’t have asked for a better tour guide in Jonathan. He was so lively, informative, and personable with our group. We had a lot of fun!”

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8.Pisa, Siena and San Gimignano Day Trip With Lunch & Wine Pairing

Discover the enchanting beauty of Pisa, Siena, and San Gimignano on a day trip filled with delicious food, exquisite wine pairings, and unforgettable memories.

★ 4.5

“Get ready to walk a ton but you will see lots of things. A great way to see different sized towns, learn history, and enjoy wine in the middle.”

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9.Chianti Safari: Tuscan Villas With Vineyards, Cheese, Wine & Lunch From Florence

Discover the ultimate Tuscan adventure with Chianti Safari! Indulge in vineyards, cheese, wine, and a delicious lunch. Escape to paradise from Florence today!

★ 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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10.Florence Sunset Walking Tour With Wine & Food Tasting

Experience the magic of Florence at sunset on our walking tour. Indulge in delicious wine and food tastings as you soak in the stunning views. Book now!

★ 5.0

“Get out there and have some fun. A great way to discover hidden Florence. Ellie was great and she took us around to show us cheese, wine, naked ravioli, and she introduced us to some very fun small biz people. Wine windows and wine cave-…”

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11.From Florence: Tuscany Day Trip With Lunch at Chianti Winery

Discover the enchanting beauty of Tuscany in a day trip from Florence. Indulge in a mouthwatering lunch at a Chianti winery. Click now for an unforgettable adventure!

★ 4.8

“What a day! Thank you Manolo for a wonderful day full of laughs and learning about the history of the Tuscany region. This was a great way to see so much of the beautiful Tuscan landscape and hospitality, topped off with a climb up the…”

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12.San Gimignano, Siena, Monteriggioni, Chianti Day Trip With Lunch & Wine Tasting

Embark on an unforgettable journey through the enchanting landscapes of San Gimignano, Siena, Monteriggioni, and Chianti. Immerse yourself in authentic Italian culture with a delightful lunch and wine tasting. Click now!

★ 4.5

“Very thorough tour with three stops plus wine tasting and lunch. Everything was arranged for you when you book, and the guides are very thorough (we had Marta, Stella, and Gennaro as our driver) and tell you about the history of the towns and the…”

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14.Chianti Wine Tour From Florence

Discover the enchanting vineyards of Chianti on an unforgettable wine tour from Florence. Indulge in the flavors of Italy and experience the essence of Tuscany.

★ 4.5

“Great experience in Toscana, the tour guide Alessandra was great, we visited two vineyards, test wines and food, and the beautiful landscape of Chianti. Our deiver Massimo was great”

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15.From Florence: Small Group Wine Tasting Tour to Tuscany

Experience the exquisite flavors of Tuscany on our small group wine tasting tour from Florence. Uncover hidden gems and indulge in the rich heritage of Italian winemaking.

★ 4.9

“We visited wonderful winerys, food and wine was excellent. Guide was super funny and the group was sweet. Worth it much more than driving and drinking on your own...”

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4.6Florence: S. Gimignano, Siena, Chianti & Wine Tasting Lunch$89.50 4.4From Florence: Chianti Half-Day Afternoon Tour$55.80 5.0Tuscany: Day Trip to Pisa, Siena, San Gimignano, and Chianti12 hours (approx.)$78.60 4.5Half Day Chianti Vineyard Escape From Florence With Wine Tastings5 hours (approx.)$53.10 4.9From Florence: Tuscany Wine & Food Tour With Guide8 hours$175 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: One Day Bike Tour Through the Hills of Chianti6 hours (approx.)$145.12 5.0Essence of Chianti Small Group Tour With Lunch and Tastings From Florence8 hours (approx.)$180.19 4.6Val DOrcia: Cheese and Wine Tasting Tour From Florence11.5 hours$108 4.5Tuscany Hills Postcard View:Val Dorcia Scenery With Wine Tasting11 hours 30 minutes (approx.)$94.57 4.4From Florence: Chianti Wine Tour With Tastings$62.63 5.0Tuscany Wine Tour7 hours (approx.)$229.77 4.3From Florence: Chianti Hills Wineries Tour With Tasting6 hours$1,166 5.0Chianti Wine Tour With Tuscan Lunch, Visit to S.Gimignano and Organic Wineries8 hours (approx.)$229.77 4.5Full Day: Wine Experience in San Gimignano, Siena & Monteriggioni11 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 From Florence:Pisa,Siena,San Gimignano & Chianti 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 4.9Florence: Countryside Tour With Wine Tasting & Pasta Class7 hours$71