Italy · WINE TASTINGS

The 15 Best Wine Tastings in Italy

115 tours  ·  from $25

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

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

★★★★★★★★★★5.0 · 21,634 reviews · 11 to 12 hours (approx.) · from $114Our pick

Join Walkabout Florence Tours for an 11 to 12-hour coach trip through Tuscany. Guides such as Alex, Sara, Davide, and Manolo lead you through Siena, a Chianti winery, San Gimignano, and Pisa. Expect Siena Cathedral, free time, farmhouse food, four wines, and a fast-paced day with plenty of walking.

“Great experience all around and beautifully coordinated. Very unique. Manolo was the best tour guide ever!”

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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

Travel from Florence to Pisa, San Gimignano, Siena, and the Chianti Hills by Wi-Fi-equipped coach. Choose guided Siena, Leaning Tower access, and a winery lunch with tasting. Guides such as Barbara, Anna, and Lila add useful local context, while free time lets you explore on your own.

“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

3.Chianti Wineries Tour with Wine Tasting

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

Ride from Florence to two Chianti wineries with an English-speaking guide, taste up to seven wines, sample cheese, salami, olive oil, and balsamic vinegar, and tour vineyards and cellars. Guides may include Martina, Cecilia, Constantino, John, or Giulia, depending on the departure.

“really fun! bigger crowd but to be expected :) informative and lovely tour of countryside”

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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

Travel from Florence to two Chianti Classico estates with an English-speaking guide such as Leo, Jonathan, or Matteo. Tour vineyards and cellars, taste reds, olive oil, cheese, salami, and bruschetta, then return in about five hours.

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

5.Tuscany & Montepulciano Day Trip with Lunch & Wine Tasting

★★★★★★★★★★4.5 · 5,232 reviews · 12 hours (approx.) · from $83

Spend about 12 hours exploring Tuscany from Rome with an English-speaking guide, a Montepulciano walking tour, lunch and wine at a local farm, and free time in Pienza. Expect scenic coach travel, steep streets, a group of up to 25, and a wine experience that varies by tour option.

“Our tour guide Barbara was very entertaining and informative. We enjoyed the views. Our favorite stop was Montepulciano. It is a long day but we are glad we did it.”

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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

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

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

From central Florence, join an English-speaking sommelier such as Ginevra, Sara, or Alex in an air-conditioned 4x4. Visit family wineries, taste Chianti, Brunello, or Vino Nobile, tour old cellars, and enjoy a regional meal with wine pairings.

“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

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

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

Spend an evening in Florence’s Oltrarno with a local English-speaking guide such as Antonella, Martino, Sara D., or Dimitri. You’ll visit wine windows, taste four Tuscan wines, sample cheese and local dishes, watch gnudi pasta being plated, learn the Negroni, and finish with 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

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

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

Join Walkabout Tours from Florence for a 12-hour coach trip through Tuscany. Explore Siena with a local guide, taste four regional wines over a farmhouse lunch in Chianti, wander San Gimignano, and see Pisa’s Leaning Tower. Guides such as Alessandro, Sara, and Giancarlo are known for lively storytelling.

“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

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

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

Spend about 11 hours exploring three medieval Tuscan towns, a Chianti winery, and Siena Cathedral. You get round-trip coach transport, three wines, vin santo, and a three-course lunch. Guides such as Sandro, Ricardo, and Martha have earned warm praise, though the pace and group size can feel demanding.

“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

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

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

Travel from Florence to Pisa, San Gimignano, Chianti, and Siena with a multilingual guide such as Marta, Aaron, Sandro, or Fabi. Expect a full 12-hour day, air-conditioned transport, Siena sightseeing, and optional lunch with three wines and Vin Santo.

“We loved the experience we had with our host and driver. Faby our tour guide was amazing”

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

11.Chianti Wine Tour from Florence

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

Leave Florence by air-conditioned coach for two organic Chianti wineries. You’ll taste six or seven Tuscan wines, sample pecorino, salami, bruschetta, olive oil, and balsamic vinegar, and learn about winemaking from local hosts. English and Spanish tours are available.

“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

12.Small Group Wine Tasting Tour to Tuscany

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

Leave Florence by air-conditioned minibus for two Chianti Classico wineries. Taste six wines with olive oil, cheese, salami, and bruschetta, tour cellars, and hear local wine stories from an English-speaking guide such as Jonathan, Leo, or Jason.

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

13.San Gimignano, Siena, and Chianti Wine Tour

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

Travel from Florence by air-conditioned minibus to Siena, a Chianti winery, and San Gimignano. You get guided context, free time, five wine tastings, olive oils, and a Tuscan meal. Guides such as Marco, Lyla, Marta, and Enrieta are praised for keeping the day friendly and well timed.

“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
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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

Travel from Florence to Monteriggioni, Siena, San Gimignano, and a Chianti estate in about 10.5 hours. Choose a guided or semi-independent Siena visit, taste two or three wines with snacks, and expect hills, a large coach, and a tightly timed day.

“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
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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

Leave central Sorrento for La Masseria, a fourth-generation family farm in the hills. Walk among lemon and olive trees, meet farm animals, taste olive oils, honey, cheese, marmalade, and limoncello, then sit down to a home-style meal with wine. Guides may include family members such as Eugenio or Raffaele.

“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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