14 Winery Tours in Italy Worth Booking

1.Chianti Wineries Tour with Wine Tasting

★★★★★★★★★★4.5 · 10,071 reviews · 5 - 5.5 hours · from $41Our pick

Travel by comfortable coach from Florence to two Chianti wineries for guided tastings, vineyard walks, and samples of cheese, salami, bread, olive oil, and balsamic vinegar. Guides such as Anna, Alex, Martina, and John have been praised for bringing Tuscany’s wine, villages, and farming traditions to life. Expect about 5 to 5.5 hours, with no hotel pickup or lunch.

“The tour was great. We had first a visit to a traditional small vineyard from a Italian family, great wine and food, and the Nona was super nice with us. We saw the grapes plantations, drank wine and they were good and had snacks. Second one was way bigger, so more comercial, but it was super cool to see the difference between them, specially cause the second one was more than 100years old. The guide knew a lot about the region, and she even gave us recommendations about Florence. Everything went well”

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

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

Spend 12 hours touring Tuscany from Florence by air-conditioned coach. Walk Siena with a local guide, visit its Duomo, enjoy a farmhouse lunch and four-wine tasting at a Chianti winery, then explore San Gimignano and Pisa. Guides such as Sara, Alessandro, Alex, and Giancarlo are known for lively commentary and careful timekeeping.

“The tour was amazing! We had Alex as our tour guide and he did an incredible job. From the minute we drove out of Florence he spoke to the history of every city we visited and everything we saw on the way there. This was perfect as it gives context to what you’re seeing. Everything on the tour was very well thought out, we couldn’t be any more pleased with how everything went. I would strongly recommend 100%. Thank you Alex!”

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3.Tuscany Wine Tour: 2 Wineries & San Gimignano from Florence

★★★★★★★★★★5.0 · 1,007 reviews · 7 hours (approx.) · from $229Top rated

Meet at Piazza della Calza at 9:45am for a 10am departure in an air-conditioned minibus. Visit two wineries near San Gimignano, taste Chianti, Vernaccia, rosé, and more with Tuscan food pairings, then enjoy 1.5 hours in town. Guides such as Emanuele, Valentina, Giovanni, and Ottavio lead the day.

“One of the best winery/Tuscany tours available. Our guide/driver was outstanding. Punctual, courteous and very knowledgeable about the wines and wineries that we were going to visit. He also took us to San Gimignano and shared with us the history of the town. This tour is a must!”

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4.Chianti Wineries Tour with Tuscan Lunch and San Gimignano

★★★★★★★★★★5.0 · 793 reviews · 8 hours (approx.) · from $229

Spend about eight hours with a guide such as Lorenzo, Daniel, Christian, or Cecilia, visiting two Chianti wineries, tasting several local wines, eating a Tuscan lunch, and wandering San Gimignano. Round-trip transport from central Florence keeps the day simple, while a stop at Piazzale Michelangelo adds a fine city view.

“Enriching experience with a professional and fun staff who paid attention to everyone’s needs. The entire tour was extremely well handled and my wife and I could not been any more pleased. Breath taking views and with detailed guide information by Leonardo is a must. The wine tasting staff were very accommodating and taught the small group how to taste and observe the quality of the wines. Learning, laughter, and scenery was an amazing experience. Thank you so much to the “Fun in Tuscany,” especially Leonardo who really went the extra mile to ensure all we’re having a great time.”

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5.Milan Urban Winery: Taste & Tour at Cantina Urbana

★★★★★★★★★★4.7 · 683 reviews · 1.5 hours · from $47

Visit Cantina Urbana Milano on Via Ascanio Sforza for a 90-minute tasting led in English or Italian. Tour the compact winery, see barrels, amphorae, and steel tanks, then sample four or six wines with local meats and cheeses. Guides such as Andrea, Irene, Francesco, and Nello explain the methods behind this unusual city winery.

“A great wine tasting with a range of wines with different flavour profiles. Our host Nello, was incredibly knowledgeable, friendly and patient. We had lots of questions, which he was happy to answer. We’ve done several wine tasting before, and the accompanying charcuterie provided was the best we’ve had. Francisco and the team at Cantina Urban were lovely, and very hospitable. We look forward to receiving the crate of wine we’ve ordered!”

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6.Guided Winery Tour with Wine Tasting

★★★★★★★★★★4.7 · 611 reviews · 1.5 hours · from $29

Visit Tenuta Adamo in the hills outside Lucca for a short cellar tour followed by a terrace tasting of local wines, olive oil, and breadsticks. English-speaking hosts such as Lisa, Julia, Luisa, and Antonio explain the winemaking process in a friendly, informal setting. Optional food platters and paid transfers can make the outing easier.

“The tour was informative, the venue was stunning with amazing views. All the staff were very friendly and knowledgeable. The wine and food were excellent”

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7.Wine Tasting Experience – Tenuta Adamo Winery

★★★★★★★★★★5.0 · 400 reviews · 1 hour 30 minutes (approx.) · from $24Best value

Meet Antonio and his team at Tenuta Adamo in the Lucca hills for a 90-minute cellar visit and tasting. You’ll sample four wines, olive oil, bread, and focaccia on the panoramic terrace. Guides such as Lisa and Lesa explain local grapes and production. Transport is not included, so plan your bus, taxi, or winery transfer ahead.

“Our visit at the winery was great! We had Lisa as a guide and she took the time to make sure we were all well looked after. She provided juice for the children and we, the adults got to taste four different wines, focaccia and meat and cheese platter. It was a lovely experience!”

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8.Chianti Delights: A Tale Of Two Wineries With A Vineyard Dinner

★★★★★★★★★★4.0 · 324 reviews · 7 hours 30 minutes (approx.) · from $106

Leave Florence at 2:45 pm for Siena, then continue through Chianti to two rustic wine estates. Expect free time in Siena, tastings of wine and olive oil, and a Tuscan meal with up to four wine pours. Guides such as Ana, Diego, Lisa, and Frederick have led recent departures, though the exact winery setup can vary.

“Siena was really nice to see, a very unusual city. Enough time to Rome around. Wine tasting and dinner were very nice and relaxed.”

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9.Visit Best Wineries in Tuscany – Wine Tasting & Tour

★★★★★★★★★★4.5 · 263 reviews · 2 hours (approx.) · from $47

At Tenuta Torciano near San Gimignano, you’ll taste Chianti, Vernaccia, rosé, Tuscan blends, olive oils, balsamic vinegar, and cantuccini with Tuscan appetizers. Staff such as Leo, Rebecca, Latisha, and Lucca may guide the tasting. Expect about two hours, no included transportation, and a polished winery setting rather than a long vineyard walk.

“We were late for our booked schedule but they accommodate us with good food and wine. The property and the people are nice”

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10.Winery Tour and Tasting

★★★★★★★★★★4.6 · 187 reviews · 1.5 hours · from $41

Meet at Talosa Cantina Storica for a 1.5-hour visit beneath Montepulciano. You’ll walk through vaulted tunnels, hear about the cellar’s past, and taste four Tuscan wines with bread and appetizers. Guides such as Luigi, Flavio, and Hector explain the wines in English or Italian.

“It was really great All of us ( adult family of 5) found it fun and informative”

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11.Wine Tasting & Lunch in a Typical Winery

★★★★★★★★★★4.6 · 183 reviews · 1.5 hours · from $65

Meet your English- or Italian-speaking guide at Talosa Cantina Storica for a 1.5-hour tour through ancient cellar vaults and tunnels. Learn how Montepulciano wine is made, taste four local wines with Tuscan specialties, then sit down to cold cuts, cheeses, and seasonal pasta. Guides may include Luigi, Hector, Flavio, or Julia.

“The tour is incredible!! So interesting! You learn a lot about wine making in the region and the underground tomb and wine barrels. Fascinating stuff! Great staff - really welcoming and knowledgeable.”

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12.San Gimignano: Lunch or Dinner at a Winery with Wine Tasting

★★★★★★★★★★4.7 · 177 reviews · 1.5 - 2 hours · from $65

At Tenuta Torciano, near San Gimignano, you’ll taste Tuscan wines and olive oils with a sommelier before a generous lunch or dinner. Guides such as Lorenzo, Marco, Mari, and Serena explain regional grapes, pairings, and tasting technique. Plan to drive yourself, since pickup and a full winery tour are not included.

“Amazing! Wine, scenery and food all top quality n. Highly recommend!”

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13.Wine and food tasting in an organic family winery

★★★★★★★★★★5.0 · 170 reviews · 2 hours 45 minutes (approx.) · from $108

Spend about 2 hours 45 minutes at Casa Lucii, a family-run organic winery near San Gimignano. With guides such as Orlando and Lucrezia, you’ll walk through the gardens, vineyard, olive grove, historic cellar, and vinsantaia, then taste eight wines with Tuscan meats, cheeses, garden produce, olive oil, chocolate pralines, and cantucci with Vin Santo.

“Excellent experience on a vineyard that’s family owned and really care about what they have and what they show you . The tour was great, food outstanding and wines exceptional”

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14.Piedmont Winery Tour: Taste Barolo, Barbaresco & Traditional Food

★★★★★★★★★★4.5 · 110 reviews · 2 hours (approx.) · from $59

Meet Carlo at Sobrero Vini in Castiglione Falletto for a two-hour walk through Barolo vineyards, cellar tour, and tasting. You’ll sample seven wines, including Barolo, Barbaresco, Barbera, and Moscato, plus Barolo Chinato and grappa with local cheese, salami, bread, and focaccia.

“La visita estuvo genial. Sobre todo la cata, y en trato del propietario, encantador en todo momento. Totalmente recomendable.”

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