15 Best Chianti Wine Tours In Florence

1-Day Tours, Chianti Wine Tours, Florence, Lunch Experiences, Pisa & Leaning Tower Day Trips, Siena & San Gimignano Day Trips, Tour Reviews, Tuscany Day Trips, Wine Tours

Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery

/ June 4, 2026

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

A full-day coach tour from Florence covering Siena, San Gimignano, Pisa, and Chianti winery lunch with wine tasting options.

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

/ June 4, 2026

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

One day Tuscany hit list: Pisa’s tower, San Gimignano medieval streets, Chianti wine lunch, and guided Siena from Florence.

★ 4.5

“We loved the activity, but the change in plans made us think we weren’t going to like the activity, as our main reason to going to Siena was pilgrimage and we arrived very early and many churches were closed. However, the experience was amazing. The destinations, the group we found and continued being friends for…”

8,393 reviews12 hoursFrom $52by Sightseeing Experience

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Florence: Chianti Wineries Tour with Wine Tasting

/ June 4, 2026

3.Florence: Chianti Wineries Tour with Wine Tasting

Half-day Chianti Hills winery tour from Florence: visit 2 authentic cantinas, taste up to 7 wines, plus olive oil, cheese, salami.

★ 4.5

“Great experience! Our guide Constantino and driver Ricardo were both fantastic. Both wineries were a good experience and had delicious wines”

8,301 reviewsFrom $56.37by Ciaoflorence Tours & Travel

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Chianti Wine Tours, Florence, Food & Drink, Tour Reviews, Tuscany Day Trips, Wine Tours

Small-Group Wine Tasting Experience in the Tuscan Countryside

/ June 4, 2026

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

Small-group Chianti wine tasting from Florence with two winery visits, vineyard tours, olive oil tastings, and local cured meats.

★ 5.0

“The bus driver, Leo, was affable and knowledgeable. So, these comments aren’t related to them. Overall, I felt like the tour was rushed. We saw a little of the grounds and vineyard at the first winery, but saw nothing of the grounds and operation act the second winery, which would have been interesting. Also, it…”

7,392 reviews4 hours 45 minutes (approx.)From $107.63by Prestige Rent

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Pisa, Siena and San Gimignano Day Trip with Lunch & Wine Pairing

/ June 4, 2026

5.Pisa, Siena and San Gimignano Day Trip with Lunch & Wine Pairing

Florence day trip to Siena, San Gimignano, and Pisa with a Tuscan winery lunch and optional wine pairing, plus guided city highlights.

★ 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 and relax in this 12 hour tour, totally worth it!…”

6,006 reviews12 hours (approx.)From $78.60by Ciao Florence Tours Srl

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SMALL-GROUP Wine Safaris: Tuscan Wine Tasting Tours from Florence

/ June 4, 2026

6.SMALL-GROUP Wine Safaris: Tuscan Wine Tasting Tours from Florence

Small-group 4x4 wine safari from Florence with off-road vineyard access, guided tastings, and a Tuscan lunch or dinner.

★ 5.0

“Gloria and Roberto were amazing guides. Not only were the wineries diverse, but the knowledge shared was informative and interesting. Gloria also took the time to answer questions and ‘get to know the group’. Roberto was a smooth and careful driver.”

5,088 reviews7 to 9 hours (approx.)From $157.21by Walkabout Florence Tours

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Chianti Wine Tours, Evening Experiences, Florence, Food, Food & Drink, Food & Wine Tours, Tour Reviews, Tours, Wine Tours

Winner 2025 Florence Sunset Food & Wine Tour by Eating Europe

/ June 4, 2026

7.Winner 2025 Florence Sunset Food & Wine Tour by Eating Europe

Florence sunset food and wine tour with a Prosecco toast, 4 Tuscan wines, a Negroni lesson at wine windows, and artisan gelato.

★ 5.0

“Fun. Great pace. Great guide. Excellent wine. Solid local dishes at small hidden gems. Plenty of food.”

5,015 reviews3 hours 30 minutes (approx.)From $149.95by Florence Food Tours by Eating Europe

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From Florence: Siena, San Gimignano, Pisa & Lunch at Winery

/ June 4, 2026

8.From Florence: Siena, San Gimignano, Pisa & Lunch at Winery

A full-day Tuscany trip from Florence with guided Siena, free time in San Gimignano, Pisa highlights, and optional Chianti lunch and wine tasting.

★ 4.8

“it was a wonderful tour even weather was rainy. Alessandro is a awesome guide. The driver was very nice. The lunch on winery is wonderful and Vine is so tasty.”

4,538 reviews12 hoursFrom $112by Walkabout Tours

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San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting

/ June 4, 2026

9.San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting

Florence day trip to San Gimignano, Monteriggioni, Siena and Chianti, with lunch and a guided wine tasting.

★ 4.5

“Beautiful lunch and towns visited, luxury coach and quality guide Constantino and Alessia / Alexa and driver Claudio was fab”

4,432 reviews11 hours (approx.)From $83.27by CAF Tour and Travel

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Florence: Pisa, Siena, S. Gimignano, Chianti Wine & Lunch

/ June 4, 2026

10.Florence: Pisa, Siena, S. Gimignano, Chianti Wine & Lunch

Guided day trip from Florence to Pisa, San Gimignano, Chianti, and Siena, with optional lunch and wine pairing on an organized coach.

★ 4.6

“We had a wonderful time, honestly, couldn’t have been better. We saw so much, never felt rushed, and experienced more of Italy than we would have on our own. Thank you so much Marta, Frederica, and Ferdinand.”

4,354 reviews12 hoursFrom $77by CAF Tour & Travel

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Chianti Wine Tour from Florence

/ June 4, 2026

11.Chianti Wine Tour from Florence

Coach tour from Florence to two Chianti wineries on the Via Chiantigiana. Tastings, local foods, and views on English tours.

★ 4.5

“The half day tour was fun but was a bit chaotic going back and forth between Italian, English and Spanish. The group was divided into groups once we reach the wineries but was so loud at the first stop I couldn’t understand a word our guide was saying. The second stop, each group was a…”

3,979 reviews5 hours (approx.)From $59.13by CAF Tour and Travel

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From Florence: Small Group Wine Tasting Tour to Tuscany

/ June 4, 2026

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

Small-group Chianti Classico wine and olive-oil tastings from Florence. Visit two estates, sample six wines, enjoy local pairings.

★ 4.9

“We had an amazing time on this tour. Rafael shared cultural fun facts with us, which was helpful for our time in Italy. The tour also got more and more fun as we tasted more wine. Highly recommend!”

3,902 reviews4.5 hoursFrom $105by Prestige Rent - Tours in Italy

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Chianti Wine Tours, Florence, Siena & San Gimignano Day Trips, Tour Reviews, Tours, Wine Tours

Siena, San Gimignano and Chianti Wines Day Tour from Florence

/ June 4, 2026

13.Siena, San Gimignano and Chianti Wines Day Tour from Florence

Full-day Tuscany trip from Florence: UNESCO Siena and San Gimignano, medieval Monteriggioni, plus Chianti tastings and snacks. From $78.60.

★ 4.5

“Ronaldo and Roberto did a great job of getting us to our destinations and communicating things to do at each stop. This tour is a large group tour on a coach bus. We still kept to our schedule. Siena is beautiful along with the other stops. The only thing i wish were different was the…”

2,542 reviews10 hours 30 minutes (approx.)From $78.60by Ciao Florence Tours Srl

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Chianti Wine Tours, Florence, Food & Drink, Lunch Experiences, Siena & San Gimignano Day Trips, Tour Reviews, Wine Tours

Florence: S. Gimignano, Siena, Chianti & Wine Tasting Lunch

/ June 4, 2026

14.Florence: S. Gimignano, Siena, Chianti & Wine Tasting Lunch

Florence to San Gimignano and Siena with Chianti lunch plus wine tasting, optional Siena Cathedral tickets, and UNESCO stops by air-conditioned bus.

★ 4.6

“It was a great trip. Sara and Placido made our day go very smooth. The towns beautiful and the wine & lunch just perfect, by the way, you also taste olive oils and balsamic vinegar. I recommend this.”

2,427 reviewsFrom $89.50by CAF Tour & Travel

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