Italy · WINE TASTINGS IN FLORENCE

15 Wine Tastings in Florence to Build a Day Around

18 tours  ·  from $52 a head

The good wine tastings in Florence fill weeks ahead and the best of them go first. Below: the 15 to lock in early, what each includes and how they differ.

Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery - The Chianti winery lunch earns its place
1-Day Tours, Florence Tours, Lunch Experiences, San Gimignano Tours, Tour Reviews, Wine Tastings, Wine Tastings in Florence, Wine Tours

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

Florence: Pisa, Siena, San Gimignano, and Chianti Experience - Meeting the coach at Santa Maria Novella
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Florence: Pisa, Siena, San Gimignano, and Chianti Experience

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

★★★★★★★★★★4.5 · 8,393 reviews · 12 hours · from $52Best value

See Pisa, San Gimignano, Siena, and Chianti in one long Tuscan day, with optional lunch, wine tasting, guides, and Leaning Tower tickets.

“Barbara was an amazing guide! She made an already amazing tour even better. Sienna was very nice. Poggio Al Laghi, the winery was very nice! Great cuts and cheese plate & a great pasta dish! The host was cool & funny. San Gimignano... what can I say.... ot was absolutely stunning & the highlight of the tour for us. It was quite, gorgeous, had midevil vibes and AMAZING views. It's one of those places that you want to move to for a few months after visiting. Pisa was overall forgettable. I highly recommend this tour!!!”

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Florence: Chianti Wineries Tour with Wine Tasting - Meeting the first cantina in the Chianti Hills
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Florence: Chianti Wineries Tour with Wine Tasting

Small-Group Wine Tasting Experience in the Tuscan Countryside - Second winery: a useful comparison, not a guaranteed full tour
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Small-Group Wine Tasting Experience in the Tuscan Countryside

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

★★★★★★★★★★5.0 · 7,392 reviews · 4 hours 45 minutes (approx.) · from $107

Visit two Chianti wineries from Florence, taste six wines with olive oil and Tuscan specialties, and enjoy a scenic small-group escape.

“We had a great guide. The two winery visits included just enough time to enjoy what they had to offer and company of the participants. There were only eleven of us!”

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SMALL-GROUP Wine Safaris: Tuscan Wine Tasting Tours from Florence - The Val d’Orcia day for Brunello and Vino Nobile
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SMALL-GROUP Wine Safaris: Tuscan Wine Tasting Tours from Florence

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

★★★★★★★★★★5.0 · 5,088 reviews · 7 to 9 hours (approx.) · from $157

Trade Florence’s streets for Chianti or Val d’Orcia on a 4x4 wine safari with cellar tours, Tuscan food, olive oil, and scenic vineyard stops.

“Sara was an amazing and knowledgeable guide with a combination of wine and historical information! Fabio was a great driver through the rainy winding roads and made the journey more comfortable and fun! We looked at a lot of tours and so happy we picked this one!”

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Winner 2025 Florence Sunset Food & Wine Tour by Eating Europe - Charcuterie in a 12th-century cellar
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Winner 2025 Florence Sunset Food & Wine Tour by Eating Europe

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

★★★★★★★★★★5.0 · 5,015 reviews · 3 hours 30 minutes (approx.) · from $149

Explore Florence’s Oltrarno over 3.5 hours with wine windows, Chianti, Negroni, local dishes, cheese, pasta, and artisan gelato.

“This food and wine tasting walking tour in Florence, on the other side of Arno River, in Oltrarno, guided by Assia, was an emotional and very inspiring experience that I would highly recommend to everyone who loves good food and wine and is eager to learn more about the history and culture of the region”

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From Florence: Siena, San Gimignano, Pisa & Lunch at Winery - Meeting the coach near Santa Maria Novella
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From Florence: Siena, San Gimignano, Pisa & Lunch at Winery

7.Siena, San Gimignano, Pisa & Lunch at Winery

★★★★★★★★★★4.8 · 4,538 reviews · 12 hours · from $112

See Siena, San Gimignano, Pisa, and Chianti in one long Tuscan day, with a winery lunch, wine tasting, expert guides, and comfortable coach travel.

“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 Leaning Tower of Pisa at sunset. Such great value for money, a must do!”

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San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting - Monteriggioni, a brief fortress stop
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San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting

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

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

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

“This was a great way to experience Tuscany if you only have a day. Comfortable bus, great locations and the included lunch/wine tasting was fantastic. Tour guide Sandro was very informative. My only recommendation would be to shorten the time in Siena - it seemed over long and made the day very long.”

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Florence: Pisa, Siena, S. Gimignano, Chianti Wine & Lunch - Pisa’s Field of Miracles in 80 Minutes
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Florence: Pisa, Siena, S. Gimignano, Chianti Wine & Lunch

Chianti Wine Tour from Florence - First winery: organic production and a local welcome
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Chianti Wine Tour from Florence

10.Chianti Wine Tour from Florence

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

Ride through Chianti from Florence, visit two organic wineries, taste Tuscan wines and foods, and enjoy a half-day in the hills without driving.

“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: Small Group Wine Tasting Tour to Tuscany - First winery: cellar lessons and three wines
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From Florence: Small Group Wine Tasting Tour to Tuscany

11.Small Group Wine Tasting Tour to Tuscany

★★★★★★★★★★4.9 · 3,902 reviews · 4.5 hours · from $105

Taste Chianti wines, olive oils, and Tuscan specialties at two estates on a relaxed half-day trip from Florence.

“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!”

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Siena, San Gimignano and Chianti Wines Day Tour from Florence - Siena, the main event
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Siena, San Gimignano and Chianti Wines Day Tour from Florence

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

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

See Siena, San Gimignano, Monteriggioni, and Chianti from Florence on a full-day coach tour with wine tasting and free time.

“I booked this tour with viator, but the tour was made with CIAO FLORENCE. It was the worst experiencie! We where in 13 people and when i bought It, It was informing that the vehicle hás 15 seats, but It was fone with a 60 seats bus, Full of people! I told to the representativos, but tbey Just ignored It!”

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Florence: S. Gimignano, Siena, Chianti & Wine Tasting Lunch - San Gimignano: towers, streets, and free time
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Florence: S. Gimignano, Siena, Chianti & Wine Tasting Lunch

From Florence: Chianti Half-Day Afternoon Tour - Finding Villa Costanza without wasting money
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From Florence: Chianti Half-Day Afternoon Tour

14.Chianti Half-Day Afternoon Tour

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

Taste seven Tuscan wines, oils, vinegar, and local snacks on a scenic half-day trip from Florence to Chianti and Monteriggioni.

“Very nice experience. Everything was perfect. The vineyards very interesting and Toscana very beautiful.”

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Tuscany: Day Trip to Pisa, Siena, San Gimignano, and Chianti - Pisa and the Field of Miracles
1-Day Tours, Florence Tours, San Gimignano Tours, Tour Reviews, Wine Tastings, Wine Tastings in Florence

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

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

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

Review of a 12-hour Tuscany day trip from Florence to Pisa, Siena, San Gimignano, and Chianti, with Siena tour, lunch, and wine tasting.

“I signed up for English speaking but the tour was combined with Spanish speakers. I find people on the bus are rude (talking)while the tour guide speaks the other language. I think because the guide needs to speak in two languages, they cut short the information given. Also 50 people is too many for a tour that contains a lot of walking. Speaking of that, we spent about 20 minutes each way in each stop walking from to/from parking to tour beginning. That’s 2 hrs wasted! Tour guides need to speak slower while speaking in other languages.”

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