15 Best Chianti Wine Tours In Florence

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

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

/ June 1, 2026

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

Florence day trip to Pisa, San Gimignano, Siena, and Chianti with free time, optional Siena guiding, and optional Leaning Tower tickets plus wine.

Florence: Chianti Wineries Tour with Wine Tasting

/ June 1, 2026

2.Florence: Chianti Wineries Tour with Wine Tasting

Half-day Chianti wine tour from Florence with two winery visits, tastings of Chianti and pairings, plus vineyard views and easy coach transport.

★ 4.5

“I really enjoyed this trip and would recommend it to everyone, you get to taste some great wines and you get to see the beautiful Tuscan landscape”

8,301 reviewsFrom $56.37by Ciaoflorence Tours & Travel

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1-Day Tours, Chianti Wine Tours, Florence, Food & Drink, Lunch Experiences, Siena & San Gimignano Tours, Tour Reviews, Tuscany Wine Tasting Tours, Wine Tours

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

/ June 1, 2026

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

San Gimignano towers, Chianti winery lunch and wine tasting, and Siena’s Duomo and Campo—an 11-hour coach day from Florence.

★ 4.5

“Awesome experience from being to end! The winery was wonderful and Cristiana or Catiana not sure about spelling was informative, kind and very friendly!”

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

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

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

/ June 1, 2026

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

Florence day trip to Pisa, San Gimignano, Chianti and Siena. Leaning Tower views, UNESCO towers, guided Siena, optional lunch+wine.

★ 4.6

“Well organized and we had a wonderful time! Martha our tourist guide is very knowledgeable and gave us clear instructions and helpful tips to make our trip seamless. Our driver Silvio has been great as well and drove us all safely to all our destinations.”

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

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Chianti Wine Tours, Florence, Tour Reviews, Tours, Tuscany Wine Tasting Tours, Wine Tours

Chianti Wine Tour from Florence

/ June 1, 2026

5.Chianti Wine Tour from Florence

Florence to Chianti: two organic winery visits, vineyard walks, cellar tastings with local food, plus scenic Via Chiantigiana 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 speaking so be mindful of conversations.”

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

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

Siena, San Gimignano and Chianti Wines Day Tour from Florence

/ June 1, 2026

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

See UNESCO Siena and San Gimignano plus Chianti wine tasting on a full-day coach tour from Florence with guided stops and free time.

★ 4.5

“group size very large almost 80 people tour operator had to deal with sharing information in 3 different languages could not set volume on headset for walking g tour lots of time on bus which could be an opportunity to share history, geography instead very little onfo from Constantine the tour leader”

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 Tours, Tour Reviews, Tuscany Wine Tasting Tours, Wine Tours

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

/ June 1, 2026

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

Florence day trip to San Gimignano, Siena and Chianti: UNESCO towns, optional cathedral visit, and lunch with a three-wine tasting.

★ 4.6

“We loved this tour. We’re got to see so many beautiful sights and the guide was very informative.”

2,427 reviewsFrom $89.50by CAF Tour & Travel

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Chianti Wine Tours, Florence, Half-Day, Tour Reviews, Tours

From Florence: Chianti Half-Day Afternoon Tour

/ June 1, 2026

8.From Florence: Chianti Half-Day Afternoon Tour

Half-day bus tour from Florence to Chianti for two winery visits, 7 wine tastings, Tuscan snacks, and medieval Monteriggioni free time.

★ 4.4

“We had a great time on this tour. We enjoyed the beautiful drive and wine tastings. The wine presentations were both informative and lots of fun.”

2,328 reviewsFrom $55.80by My Tour in Italy

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1-Day Tours, Chianti Wine Tours, Florence, Pisa Day Trips, Siena & San Gimignano Tours, Tour Reviews, Tuscan Countryside Tours

Tuscany: Day Trip to Pisa, Siena, San Gimignano, and Chianti

/ June 1, 2026

9.Tuscany: Day Trip to Pisa, Siena, San Gimignano, and Chianti

One day from Florence to Pisa, Siena, San Gimignano, and Chianti wine. Guided walks, a winery lunch, and iconic sights at a steady pace.

★ 5.0

“Pisa was not an overrated experience prior to what we've heard before. A tour like this is perfect for these locations. San Gimignano was nice, but the highlight for sure was the winery and lunch. Siena was also beautiful, but once your done you will be tired, so prepare for a full day!”

2,283 reviews12 hours (approx.)From $78.60by CAF Tour and Travel

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Chianti Wine Tours, Florence, Tour Reviews, Tuscany Wine Tasting Tours, Wine Tours

Half day Chianti Vineyard Escape from Florence with Wine Tastings

/ June 1, 2026

10.Half day Chianti Vineyard Escape from Florence with Wine Tastings

Half-day Chianti wine escape from Florence with two winery stops, vineyard walks, cellar visits, and tastings on the Chianti Road.

★ 4.5

“The wineries were wonderful and the tour overall was enjoyable. However, the tour guide was not very engaging and spent most of the time chatting with the driver, which made her presence feel unnecessary.”

2,196 reviews5 hours (approx.)From $53.10by Ciao Florence Tours Srl

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Chianti Wine Tours, Florence, Lunch Experiences, Motorbike & Scooter Rentals, Scooter Rentals, Tour Reviews, Tours, Vespa, Bike & Golf Cart Tours

Chianti Vespa Tour with Lunch from Florence & E-car Option

/ June 1, 2026

11.Chianti Vespa Tour with Lunch from Florence & E-car Option

Ride a Piaggio Vespa or Topolino e-car through Chianti from Florence, stop in small villages and wineries, and enjoy a Tuscan lunch.

★ 5.0

“Great experience! Definitely worth it! Our guides were Chiara and Carlotta and they were awesome. Tour starts with 30 minutes bus ride to Vespa location where you practice riding. Guides were very helpful. The ride on the Vespas was around 1.5 hours through the country roads. Recommend being a passenger so you can take in…”

1,453 reviews6 hours 30 minutes (approx.)From $125.28by Towns of Italy

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Chianti Wine Tours, Cycling Tours, Florence, Food & Drink, Tour Reviews, Tours, Tuscan Countryside Tours, Tuscany Wine Tasting Tours, Vespa, Bike & Golf Cart Tours, Wine Tours

Tuscany Bike Tours Through the Chianti Hills with Wine Tasting

/ June 1, 2026

12.Tuscany Bike Tours Through the Chianti Hills with Wine Tasting

Cycle through Chianti hills from Florence, stop for photos, then taste Chianti wine and olive oil at a medieval castle with lunch.

★ 5.0

“It was a great excursion but I didn’t realize there were other options in terms of electric bike and moped vs regular cycling. It turns out I’m not fit enough to cycle up and down hills for 2 hours. I did it and lived to tell about it, but I should have chosen the electric…”

1,300 reviews6 hours (approx.)From $145.12by Tuscany Bike Tours

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Chianti Wine Tours, Florence, Lunch Experiences, Tour Reviews, Tours

Essence of Chianti Small Group Tour with Lunch and Tastings from Florence

/ June 1, 2026

13.Essence of Chianti Small Group Tour with Lunch and Tastings from Florence

Small-group Chianti day trip from Florence with 3 wineries, olive oil tastings, a Tuscan lunch, and a Greve village break.

★ 5.0

“Excellent. Daniele as tour guide and Alessio as driver are a great team. The wineries visited were beautiful and hospitable, and the wine was good. I learned a lot about Chianti wine.”

1,269 reviews8 hours (approx.)From $180.19by Prestige Rent

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Chianti Wine Tours, Florence, Tour Reviews, Tours, Tuscany Wine Tasting Tours, Wine Tours

From Florence: Chianti Wine Tour with Tastings

/ June 1, 2026

14.From Florence: Chianti Wine Tour with Tastings

Half-day Chianti tour from Florence: visit 2 organic wineries with tastings, scenic hills, and local food like pecorino and olive oil.

★ 4.4

“Everything went great. The first winery was small, cozy, and overall it was not bad. The second winery was simply the best part. An interesting and funny employee who told us about wine and all the processes. He joked with us, let us try many of his products. He answered all the questions. The tour…”

1,025 reviewsFrom $62.63by CAF Tour & Travel

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