The 15 Best Chianti Wine Tours from Florence

Florence: Pisa, Siena, San Gimignano, and Chianti Experience - Meeting in Santa Maria Novella and staying on schedule

★★★★★★★★★★4.5 · 8,393 reviews · 12 hours · from $52Our pick

One 12-hour Tuscany day trip from Florence with Pisa, San Gimignano, Siena and Chianti, plus optional lunch, wine, and Leaning Tower tickets.

“Our guide Hillary was very knowledgable and provided excellent explanations of the places that we visited including their history and some curiosities as well as some recommendations of places to visit and traditional food to taste. The tour was very well organised and allow us to have a good insight into the region. Our bus driver Salvatore was also really nice and we appreciate his contribution to the success of the tour. I would recommend this tour to anyone visiting Firenze.”

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Florence: Chianti Wineries Tour with Wine Tasting

2.Chianti Wineries Tour with Wine Tasting

★★★★★★★★★★4.5 · 8,301 reviews · from $56

Half-day Chianti tour from Florence with two winery visits, vineyard walks, and tastings of up to 7 wines plus Tuscan bites on a GT bus.

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

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

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

★★★★★★★★★★4.5 · 4,432 reviews · 11 hours (approx.) · from $83

San Gimignano, Monteriggioni, Chianti winery lunch and wine tasting, plus Siena with optional cathedral access, all by coach from Florence.

“We had a day trip to San Gimignano and Siena. The tour was amazing and well-managed. All thanks to Alessandra and Enrico. The lunch and wine tasting experience were good. The guided visit to Siena was merged with another language, thus, making it difficult to understand.”

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

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

★★★★★★★★★★4.6 · 4,354 reviews · 12 hours · from $77

Florence to Pisa, San Gimignano, Siena and Chianti hills in one guided day, with optional lunch and wine pairing included.

“I highly recommend this tour! Everything was perfectly organized from start to finish. The bus was comfortable, and the scenery along the way was absolutely stunning. The guides were friendly, attentive to every detail, and provided excellent explanations in both English and Spanish. The places we visited were beautiful and full of charm. If you choose the option with lunch included, you’ll enjoy a delightful meal at a lovely restaurant, complete with a small wine tasting. Every stop was worth it. A truly unforgettable experience. I would definitely do it again without hesitation!”

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Chianti Wine Tour from Florence

5.Chianti Wine Tour from Florence

★★★★★★★★★★4.5 · 3,979 reviews · 5 hours (approx.) · from $59

Half-day Chianti Wine Tour from Florence with coach ride, 2 organic winery visits, vineyard and cellar tours, and tastings of 6 to 7 wines.

“Not a lot of time spent at each winery. There is a steep hill to climb to get to one of the wineries.”

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From Florence: San Gimignano, Siena, and Chianti Wine Tour

6.San Gimignano, Siena, and Chianti Wine Tour

★★★★★★★★★★4.5 · 3,762 reviews · from $164

A 9-hour small-group Tuscany tour from Florence, mixing Siena, San Gimignano, and Chianti with lunch and five wine tastings.

“Our guide (I believe it was Emma) was incredibly lovely, funny and had lots of knowledge of Siena especially since it’s her hometown. The bus was comfy and seemed brand new, air conditioning was a relief too! The trip is very long, so I think the last stop was tough since it was nearly two hours, could’ve done just an hour I think.”

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Siena, San Gimignano and Chianti Wines Day Tour from Florence

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

★★★★★★★★★★4.5 · 2,542 reviews · 10 hours 30 minutes (approx.) · from $78

See Siena and San Gimignano plus Monteriggioni and Chianti wine tasting on a 10.5-hour coach tour from Florence.

“Lovely full day of activities. Fun for families as you are driven by bus. However the private bus cannot stop at locations close to the old city gates so there is a large amount of walking up steep hills to get to town entrances. A public bus takes you right to the city entrances but you would need acfew days to do what we did in one full day of nearly 12 hours. A few incidents delayed our departure from locations so this is really a 12 hour tour. Fun, exciting with Joe our super tour guide!”

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

8.S. Gimignano, Siena, Chianti & Wine Tasting Lunch

★★★★★★★★★★4.6 · 2,427 reviews · from $89

Florence to San Gimignano and Siena with a Chianti winery lunch and 3-wine tasting, plus optional Siena Cathedral tickets.

“We had a lovely time our tour. Martha and Enrico were great! For an all day tour, you do not feel like you’re on the bus for too long between destinations. Our tour leader gave us recommendations of what to do in our free time including activities and food/drink to try before we arrived. Be aware that if it is off season, many things are closed or may open later but you can always find somewhere to eat or drink and it’s nice to walk around when it’s quieter. Our guide Marco at the winery was fun. Lunch was a plate of cold meats, bread and a pasta. Dessert was…”

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From Florence: Chianti Half-Day Afternoon Tour

9.Chianti Half-Day Afternoon Tour

★★★★★★★★★★4.4 · 2,328 reviews · from $55

Half-day Chianti wine tour from Florence with two estates, seven wine tastings, oil and balsamic samples, and time in Monteriggioni.

“We had a great time. It was well organized and our tour guide was excellent. The bus was very comfortable, as well. The only thing I would add to help others in the future is to emphasize to take the local train to the meeting spot = which cost like 6E. We took an Uber costing us $60 😭 But nonetheless we had a great time at both wineries.”

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

10.Day Trip to Pisa, Siena, San Gimignano, and Chianti

★★★★★★★★★★5.0 · 2,283 reviews · 12 hours (approx.) · from $78Top rated

Florence day trip to Pisa, Siena and San Gimignano with Chianti views. Winery lunch includes tasting of 4 wines and guided touring.

“It was well organised, on time and very interesting. Christiana and Ellis were excellent ambassadors for your company. We really enjoyed every aspect.”

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Half day Chianti Vineyard Escape from Florence with Wine Tastings

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

★★★★★★★★★★4.5 · 2,196 reviews · 5 hours (approx.) · from $53

Half-day Chianti wine escape from Florence with two estate tastings, cellar and vineyard walks, and countryside photo stops on Strada 222.

“Excellent tour. Our guide was exceptionally attentive and informative. Would highly recommend this tour.”

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

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

★★★★★★★★★★5.0 · 1,453 reviews · 6 hours 30 minutes (approx.) · from $125

Ride a Piaggio Vespa or Fiat Topolino e-car through Chianti, visit wineries for tastings, and enjoy Tuscan lunch outside Florence.

“This was so much fun. One of the best ways to see the Tuscan countryside. Our guides yo and Julia were very friendly and knowledgeable.”

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Tuscany Bike Tours Through the Chianti Hills with Wine Tasting

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

★★★★★★★★★★5.0 · 1,300 reviews · 6 hours (approx.) · from $145

Cycle from Florence through the Chianti hills for 2 hours, then enjoy wine and olive oil tasting at a medieval castle with lunch.

“Do not hesitate for one single second to book this tour! We had such a wonderful family experience with the kind assistance of all involved. There were three tour guides (Allesio, Filippo, and Ben), and Lorenzo, the travel assistant who shadowed our ride to provide assistance anytime it was needed. Each individual was exceptionally upbeat and pleasant to be with, so much so that we wanted to invite them to join us for drinks and dinner that evening! Unfortunately, we had another commitment that made that impossible … next time guys!! The tour was super informative, we learned a LOT, thank you Alessio! The winery tour was fascinating, and man…”

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

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

★★★★★★★★★★5.0 · 1,269 reviews · 8 hours (approx.) · from $180

Small-group Chianti tour from Florence with 3 winery tastings, Tuscan lunch, and a Greve village stop, finished with scenic views.

“It was such a good time! Jason and Sergio were amazing hosts. Beautiful countryside, great wine, good people!”

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From Florence: Chianti Wine Tour with Tastings

15.Chianti Wine Tour with Tastings

★★★★★★★★★★4.4 · 1,025 reviews · from $62

5 hours from Florence to two Chianti wineries with cellar tours, organic tastings, Chianti plus Supertuscan, and local bites.

“Our guide was very nice, but it was very difficult to hear her and make out what she said. Other than that she was excellent though in keeping us in time and giving recommendations. The tour was fantastic, especially the second bigger winery. So informative and so generous with the samples!”

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