Italy · WINE TOURS

Wine Tasting in Italy: The 15 Best Cellar Visits

104 tours  ·  from $25 a head

Barolo in the fog, Chianti on the hills, Prosecco on the slopes above Treviso. These 15 tastings are priced by the glass count, with transport notes for the ones that end well after lunch.

Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery - Starting at Santa Maria Novella Station
1-Day Tours, Chianti & Tuscan Countryside Tours, Lunch Experiences, Tour Reviews, Tours in Florence, Wine Tours, Wine Tours in Florence

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

Spend 11 to 12 hours touring Tuscany by air-conditioned coach, with guided Siena highlights, free time in San Gimignano and Pisa, and an optional farmhouse lunch with four wine tastings. Guides such as Sara, Davide, Alex, and Manolo are praised for keeping this busy day clear, friendly, and on schedule.

“Manolo and his team took great care of us and were so knowledgeable about all the places we went to. The sights were fabulous and the winery was absolutely exceptional! We had plenty of free time to explore, buy some souvenirs and make life long memories.”

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Florence: Chianti Wineries Tour with Wine Tasting - The first hour: Florence to the Chianti Hills
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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

Leave Florence by comfortable coach for two Chianti wineries. You’ll tour vineyards and cellars, taste three to four wines at each stop, and sample cheese, salami, bread, olive oil, and balsamic vinegar. Guides such as Martina, Cecilia, and Constantino have helped make this half-day outing lively, though group sizes can be large and food portions are light.

“Both wineries we visited were beautiful and the hosts were joyful and hospitable. Our guide shared interesting information about the wine region; she was cheerful and kind. The bus ride gave us scenic views of the area. What a great experience! We absolutely loved it. Our favorite thing, besides the great wine, was meeting guests on our tour from all over the world.”

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Small-Group Wine Tasting Experience in the Tuscan Countryside - First estate: vineyard, cellar, and three wines
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Small-Group Wine Tasting Experience in the Tuscan Countryside

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

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

Leave Florence from Santa Maria Novella station for two Chianti Classico wineries. Tour vineyards and cellars, taste six or more regional wines, and sample olive oil, cheese, salami, cured ham, and bruschetta. Guides such as Leo, Matteo, Jonathan, and Leonardo add local history and practical wine tips.

“Do it, such a great experience and great tour guide. So fun and the perfect amount of time, and great value.”

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Rome: Tuscany & Montepulciano Day Trip with Lunch & Wine Tasting - Montepulciano, Tuscany’s wine town
1-Day Tours, Chianti & Tuscan Countryside Tours, Food & Drink, Lunch Experiences, Tour Reviews, Tours in Rome, Wine Tours, Wine Tours in Rome

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

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

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

Ride from central Rome to Montepulciano and Pienza with an English-speaking guide, then enjoy a three-course farm lunch with Tuscan wines, including Brunello di Montalcino. Guides such as Anna, Barbara, Antonino, and Flavio have been praised for lively history and practical tips. Expect a long day, steep streets, and limited free time.

“Antonino is a good and accomodating tour guide with Max as our excellent and courteous driver. A gentleman indeed. Helping us always. Highly recommended tour.”

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SMALL-GROUP Wine Safaris: Tuscan Wine Tasting Tours from Florence - Choosing between Chianti and Val d’Orcia
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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

Leave central Florence for a 4x4 wine safari through Chianti or Val d’Orcia. With an English-speaking sommelier guide such as Ginevra, Sara, or Alex, you’ll visit family wineries, taste wine, olive oil, cheese, and salumi, and share a Tuscan lunch or dinner. Choose a 7-hour half-day option or a longer full-day route.

“What an amazing experience, our tour guide Ginebra “Ginny” is exceptional, educated, very informative and passionate about the art of wine making. The locations that are part of this tours are breathtaking, the wine was some of the best wines I have tasted and the driver Christophe is an excellent driver. I can ramble on about the driver, tour guide, vineyards and restaurant .. just understand that this experience is a must.”

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Winner 2025 Florence Sunset Food & Wine Tour by Eating Europe - DiVin Boccone brings wine and charcuterie into an old 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

Spend an evening crossing Florence’s Oltrarno neighborhood with a local English-speaking guide such as Antonella, Dimitri, Sara D., or Martino. You’ll visit small food shops, historic trattorias, and two wine windows while tasting Prosecco, Tuscan wines, cheese, pasta, soup, wild boar stew, a Negroni, and artisan gelato. The group is limited to 13 people.

“Eli was fantastic. She guided us on a wonderful food and wine journey through Florence. Her knowledge and passion elevated the experience providing unique insights and history. Highly recommend!”

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From Florence: Siena, San Gimignano, Pisa & Lunch at Winery - Siena: Gothic stone, yellow walls, and Piazza del Campo
Chianti & Tuscan Countryside Tours, Lunch Experiences, Tour Reviews, Tours in Florence, Wine Tours, Wine Tours in Florence

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

Travel from Florence by comfortable coach to Siena, San Gimignano, Chianti, and Pisa. You’ll tour Siena with a local guide, visit the Gothic cathedral, enjoy an optional farmhouse lunch with four Tuscan wines, and finish at the Leaning Tower. Guides such as Sara, Alessandro, and Manolo are known for keeping the long day lively and well organized.

“It was convenient and comfortable. On time for drop and pick up. The guide was really good. Especially, a boat tour was good for us. Driving was safe. The driver was wonderful.”

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San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting - Monteriggioni: a small fortress with a short visit
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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

Spend 11 hours touring Tuscany by coach, with free time in San Gimignano and Monteriggioni, a three-course winery lunch, three Chianti wines, and Siena sightseeing. Select the Siena guide and cathedral upgrade for a fuller visit. Guides such as Sandro, Marta, Ricardo, and Ilaria are praised for clear, friendly service.

“Sandro and Fabi were fantastic, well organised and very informative. Great meal and wine tasting too! Even the rain couldn't dampen the mood.”

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Chianti Wine Tour from Florence - Riding the Via Chiantigiana into the hills
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Chianti Wine Tour from Florence

9.Chianti Wine Tour from Florence

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

Leave Florence by air-conditioned coach for two Chianti wineries along the Via Chiantigiana. You’ll taste six or seven Tuscan wines, sample cheese, salami, bruschetta, olive oil, and balsamic vinegar, and tour vineyards and cellars with local hosts. Guides such as Aaron, Cristina, Alessandra, and Maria Luisa have helped make this five-hour outing especially engaging.

“Both wineries were amazing! Lots of Knowledge about making the wine and very personal wanted you to ask questions and just talked to you during the tour. Tommas from the second location super friendly and did an excellent job! Both shipped to the US and you could buy another glass while you walked around the site. Both had some snacks at the venues, but would eat lunch or dinner before going.”

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From Florence: Small Group Wine Tasting Tour to Tuscany - The first estate, cellar traditions and three wines
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From Florence: Small Group Wine Tasting Tour to Tuscany

10.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 about six wines and local olive oils with cheese, salami, cold cuts, and bruschetta. English-speaking guides such as Jason, Leo, Jonathan, and Raffaele have helped make this a lively, social outing, though the wineries and guide can vary.

“This tour was incredible from start to finish! The scenery was breathtaking. The wine tasting was fantastic, with a great selection of local wines that were both delicious and unique. Our guide was friendly, knowledgeable, and made the whole experience even more enjoyable with interesting stories and insights about the region. Everything was perfectly organized and relaxed. We couldn’t have asked for a better day — highly recommend this tour to anyone visiting Tuscany! 🍷🌻🇮🇹”

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From Florence: San Gimignano, Siena, and Chianti Wine Tour - Siena and the 85-minute introduction
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From Florence: San Gimignano, Siena, and Chianti Wine Tour

11.San Gimignano, Siena, and Chianti Wine Tour

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

Travel from Florence to Siena, a Chianti winery, and San Gimignano in about nine hours. Expect an air-conditioned minibus or coach, multilingual guidance, five wine tastings, Tuscan specialties, and free time in both medieval towns. Guides such as Marco, Lyla, Marta, and Enrieta are praised for keeping the day clear, friendly, and on schedule.

“The experience couldn’t get any better. Marco is an excellent guide and a person! Highly recommended. I went by myself, but made very good friends along the way 💫 Italy is mesmerizing and do not hesitate to take this tour 🥰🌟 p.s. I would recommend to get lunch at the winery. Grazie”

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Rome Food Tour: Unlimited Tastings with Fine Wine & Barolo - La Nicchia Cafè Starts With a Serious Italian Tasting
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Rome Food Tour: Unlimited Tastings with Fine Wine & Barolo

12.Rome Food Tour: Unlimited Tastings with Fine Wine & Barolo

★★★★★★★★★★5.0 · 3,365 reviews · 4 hours (approx.) · from $83

Meet near Cipro Metro for four hours of Roman food and wine in Prati. Guides such as Michael, Giordano, Vincenzo, and Irene lead tastings at La Nicchia, Bonci Pizzarium, Paciotti Salumeria, Il Segreto, and Lemongrass Ice Cream. Expect up to 20 tastes, Roman pasta, truffles, Barolo, gelato, and plenty of walking.

“Michael did a great job teaching us about the wine and food we tasted. Had a great time meeting and talking to the other people on the tour.”

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

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

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

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

Meet in central Sorrento and ride into the hills to La Masseria Farm, a fourth-generation family property. With family guides such as Eugenio and Raffaele, you’ll walk among lemon and olive trees, learn how the farm makes its products, taste honey, cheese, marmalade, olive oils, and limoncello, then enjoy a generous farm-to-table lunch with wine.

“We loved meeting the family of the farm and the tour! Lots of interesting information about how the lemon trees are grown and the olive oil is made! We learned a lot more than we expected to, and this is coming from a lemon LOVER!! We loved feeding the animals and laughing with the family and others with our tour. Definitely recommend this experience!! The food was also delicious! Thank you guys so much for a great tour on our honeymoon!”

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Naples: Pompeii and Mt. Vesuvius with Lunch and Wine Tasting - Lunch at a vineyard, with more food than the word light suggests
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Naples: Pompeii and Mt. Vesuvius with Lunch and Wine Tasting

14.Pompeii and Mt. Vesuvius with Lunch and Wine Tasting

★★★★★★★★★★4.5 · 2,454 reviews · from $141

Spend a full day combining Pompeii, Mount Vesuvius, and Campanian food and wine. A professional archaeologist leads your two-hour Pompeii visit, then you stop at a local vineyard for lunch and tasting before choosing the crater trail or the more adventurous Valley of Hell route. Pickup is available from central Naples locations.

“Giovanni was a great guide very kind and knowledgeable. His jokes made the trip fun and exciting. Giacomo was an experienced driver you can tell he knew the city and how to navigate it. Both sites were very fun to visit and the wine tasting was amazing!”

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Florence: S. Gimignano, Siena, Chianti & Wine Tasting Lunch - San Gimignano: two hours among the towers
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Florence: S. Gimignano, Siena, Chianti & Wine Tasting Lunch

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

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

Travel from Florence by air-conditioned coach to San Gimignano, Monteriggioni, Siena, and a Chianti winery. You get free time in San Gimignano, a three-course lunch with three wines, and an optional guided Siena Cathedral visit. English and Spanish tours are available, with guides such as Marta, Aaron, Ricardo, and Sara leading some departures.

“Our tour guide Aaron was the best! Can’t really ask more.”

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