Italy · WINE TASTINGS

The 15 Best Wine Tastings in Italy

40 tours  ·  from $25 a head

Sangiovese in the Chianti hills, Nebbiolo under Piedmont fog, Nerello grown on black volcanic sand. These 15 tastings are priced by the pour, with transport notes for the ones that finish well after lunch.

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
Florence Tours, San Gimignano Tours, Tour Reviews, Wine Tastings, Wine Tastings in Florence

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
Florence Tours, Food & Drink, Food Tours in Florence, Tour Reviews, Tours, Wine Tastings, Wine Tastings in Florence, Wine Tours

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
Florence Tours, Food & Drink, Food Tours in Florence, Tour Reviews, Wine Tastings, Wine Tastings in Florence, Wine Tours

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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Rome: Tuscany & Montepulciano Day Trip with Lunch & Wine Tasting - Montepulciano: wine, towers, and steep stone streets
1-Day Tours, Food & Drink, Food Tours in Rome, Lunch Experiences, Rome Tours, Tour Reviews, Wine Tastings, Wine Tastings in Rome, Wine Tours

Rome: Tuscany & Montepulciano Day Trip with Lunch & Wine Tasting

SMALL-GROUP Wine Safaris: Tuscan Wine Tasting Tours from Florence - The Val d’Orcia day for Brunello and Vino Nobile
Florence Tours, Food & Drink, Food Tours in Florence, Tour Reviews, Tours, Wine Tastings, Wine Tastings in Florence, Wine Tours

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

6.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
Evening Experiences, Florence Tours, Food, Food & Drink, Food Tours in Florence, Tour Reviews, Tours, Wine Tastings, Wine Tastings in Florence, Wine Tours

Winner 2025 Florence Sunset Food & Wine Tour by Eating Europe

7.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
Florence Tours, Lunch Experiences, San Gimignano Tours, Tour Reviews, Wine Tastings, Wine Tastings in Florence, Wine Tours

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

8.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
1-Day Tours, Florence Tours, Food & Drink, Food Tours in Florence, Lunch Experiences, San Gimignano Tours, Tour Reviews, Wine Tastings, Wine Tastings in Florence, Wine Tours

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

9.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
Florence Tours, Lunch Experiences, Tour Reviews, Wine Tastings, Wine Tastings in Florence, Wine Tours

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

Chianti Wine Tour from Florence - First winery: organic production and a local welcome
Florence Tours, Tour Reviews, Tours, Wine Tastings, Wine Tastings in Florence, Wine Tours

Chianti Wine Tour from Florence

11.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
Florence Tours, Food & Drink, Food Tours in Florence, Tour Reviews, Tours, Wine Tastings, Wine Tastings in Florence, Wine Tours

From Florence: Small Group Wine Tasting Tour to Tuscany

12.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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From Florence: San Gimignano, Siena, and Chianti Wine Tour - Siena: brick streets and the Piazza del Campo
San Gimignano Tours, Siena & Tuscan Hill Towns Tours, Tour Reviews, Tours, Wine Tastings, Wine Tastings in Siena, Wine Tours

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

13.San Gimignano, Siena, and Chianti Wine Tour

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

See Siena, a Chianti estate, and San Gimignano in one full day, with five wines, Tuscan food, and free time in medieval towns.

“Oh such a lovely day it was and our guide Lyla was very communicative and made the tour very fun. Our driver, Antonio, was also a very sweet person. She explained about the very interesting history of places and the wines too. There was intern from the company who also gave a lot of information about the last stop. Overall, it was great day, relaxed and every minute of the tour was used. The cherry on top was everybody and everything was on time. Highly recommend this tour.”

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Siena, San Gimignano and Chianti Wines Day Tour from Florence - Siena, the main event
Florence Tours, San Gimignano Tours, Tour Reviews, Tours, Wine Tastings, Wine Tastings in Florence, Wine Tours

Siena, San Gimignano and Chianti Wines Day Tour from Florence

14.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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Sorrento Farm and Food Experience including Olive Oil, Limoncello, Wine tasting - Walking through lemon and olive terraces
Amalfi Coast Tours, Dining Experiences, Farms, Food, Food & Drink, Food Tours in the Amalfi Coast, Tour Reviews, Wine Tastings, Wine Tours

Sorrento Farm and Food Experience including Olive Oil, Limoncello, Wine tasting

15.Sorrento Farm and Food Experience including Olive Oil, Limoncello, Wine tasting

★★★★★★★★★★5.0 · 2,524 reviews · 4 hours (approx.) · from $114

Tour Sorrento’s family farm for lemon groves, olive oil, limoncello, wine, tastings, and a generous farm-to-table lunch.

“This was one of our favorite activities while in Sorrento! Eugene and his family were wonderful hosts and we enjoyed learning about the history of the land and their farm. The meal at the end was excellent! I highly recommend this tour.”

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