Where to Go Private: the 15 Best Luxury Wine Tours in Italy

1.Exclusive Prosecco Wine Tour from Venice – Small Group

★★★★★★★★★★5.0 · 189 reviews · 6 hours (approx.) · from $199Our pick

Leave Venice with sommelier Riccardo for a six-hour trip into the Valdobbiadene Prosecco Hills. Visit two small family wineries, taste up to eight wines, enjoy salami, cheese, pizza, and focaccia, and return to Piazzale Roma by air-conditioned vehicle.

“We had an absolutely wonderful experience on our Prosecco tour, and it was all thanks to our fantastic guide Ricardo. From start to finish, he was knowledgeable, professional, and genuinely passionate about the region and its wines. The explanations about the Prosecco-making process were clear and engaging, and we loved learning about the history of the area while visiting beautiful vineyards and wineries. Ricardo made the day feel relaxed yet well-organized, always making sure we were comfortable and enjoying ourselves . What truly set this tour apart was the personal touch—great recommendations, thoughtful answers to our questions, and a warm, friendly attitude that made the experience fe...”

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2.Pic nic Deluxe Assisi and wine tasting 5 wines

★★★★★★★★★★4.8 · 88 reviews · 2.5 hours · from $52

At SAIO, a family-run winery about 800 meters from the Basilica of Saint Francis, you’ll taste five wines, follow vineyard information boards, and walk to a veranda picnic with Umbrian bread, cheese, cured meats, Torta al Testo, cookies, and one bottle of wine per couple.

“Friendly and welcoming staff, a beautiful and gentle walk amidst the groves. A georgeous view at the picnic spot that was accompanied by amazing food. They provided a vegan delight for me and it was incredible. Definitely recommend.”

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3.Bolgheri: Premium Wine Tasting with Winery Tour

★★★★★★★★★★5.0 · 88 reviews · 1 hour 15 minutes (approx.) · from $66

At Terre del Marchesato near Bolgheri, a multilingual guide takes you from vineyard to cellar, explaining the family estate and its wine methods. You taste Cabernet Sauvignon, Merlot, Petit Verdot, and extra-virgin olive oil with bruschetta. The small-group visit lasts about 75 minutes.

“This was a truly amazing experience. We had a very informative tour of the winery with the arborist who showed such passion for his work. The wines were fantastic and we had a food pairing as well that was delicious! Very worth the visit.”

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4.Premium Prosecco Hills Winery Tour with Prosecco Tastings & Food

★★★★★★★★★★4.5 · 80 reviews · 5 hours (approx.) · from $247

Paolo drives you from Venice to the Prosecco Hills, where a family-run winery explains DOCG production and pours four premium wines with local meats, cheese, bread, and breadsticks. The group is capped at four, making this a relaxed, personal half-day outside the city.

“Paolo was so informative and very gracious. I traveled with my daughter studying abroad to see the country. He was a great tour guide and the vineyard was beautiful. The pairings of Prosecco with the lunch was excellent.”

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5.Exclusive Private Tuscany Wine Tour & Food Pairing Session

★★★★★★★★★★5.0 · 70 reviews · 8 hours (approx.) · from $603

Set out from Florence with a private driver-guide, often Anna, Paola, or Frederico, for three contrasting Chianti wineries. Taste local wines, enjoy a full Tuscan lunch with pairings, visit olive groves, and take scenic country roads in a private air-conditioned minivan.

“Wonderful visit with a great host. Our guide was great and easy to talk to. The wineries were so friendly and inviting. The tour provides a lot of education on the region and wine making. I'd definitely recommend the tour.”

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6.San Gimignano: Premium Wine Tour with Lunch

★★★★★★★★★★4.9 · 66 reviews · 2.5 hours · from $77

At Tenuta Guardastelle, a live English or Italian guide leads you through the vineyards and cellar before a Tuscan lunch on the terrace or in the dining room. Taste five wines, including Vernaccia di San Gimignano, Chianti Riserva, and a Supertuscan, plus local cheese and olive oil.

“El viñedo es bellísimo, muy buena explicación y la comida y los vinos deliciosos, una excelente experiencia.”

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7.Pic nic Deluxe Assisi for 2 and wine tasting 5 wines

★★★★★★★★★★5.0 · 63 reviews · 2 hours 30 minutes (approx.) · from $53

At SAIO winery near Assisi, you taste five wines, choose a bottle for two, then follow a self-guided vineyard walk to a picnic of Umbrian cheeses, cured meats, savory cakes, dessert, and local olive oil. Francesca and Agnese are among the hosts who may lead the tasting.

“Amazing view of Assis while tasting high quality wine tasting delicious picnic Great hospitality and knowledege Lovely”

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8.Montalcino: Premium Wine Tasting with light-lunch and Tour

★★★★★★★★★★4.8 · 49 reviews · 2 hours · from $105

At Il Paradiso di Cacuci, guide Francesco leads a private two-hour visit through the vineyards and cellar, followed by Brunello, Rosso, Rosato, Super Tuscan, grappa, and a three-course 0-mile Tuscan lunch. The tasting is by appointment in Italian or English.

“A chegada até o local, usando o Google Maps foi precisa. A receptividade, através do cicerone Francesco, foi excelente. Recebemos uma aula inicial do plantio e colheita das uvas usadas na fabricação dos vinhos da Casa, em especial dos Brunellos de Montaltino. Na sequência a degustação de 06 tipos de vinhos fabricados, dos mais leves até os mais encorpados (de Reserva e Gran Reserva), foi ótima, seguida de um almoço leve de 3 pratos. Portanto, foi uma experiência marcante!”

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9.Exclusive Winery Tour with Tasting and Dinner in Chianti vineyard

★★★★★★★★★★4.5 · 49 reviews · 6 hours 30 minutes (approx.) · from $144

Leave Florence at 3 p.m. for two Chianti wineries, cellar lessons, tastings, a Greve village stop, and a seasonal Tuscan dinner among the vines. Guides such as Lucy, Nico, and Stefano have led engaging outings, while vegetarian and vegan meals are available by request.

“The guide was humorous and knowledgeable, both wineries were different to each other but still imteresting”

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10.Tenute Girolamo: Winery tour and Premium Tasting in the Itria Valley

★★★★★★★★★★4.8 · 38 reviews · 2 hours · from $35Best value

At Tenute Girolamo near Martina Franca, an English or Italian guide leads you through the winery and barrel cellar before serving four wines with Apulian cheeses, cold cuts, friselline, and focaccia. Allow two hours, with visits at 10:30 a.m., 12:30 p.m., or 3 p.m.

“Mi è piaciuto molto, si potrebbe migliore un po la parte degustazione. In ogni caso è stata una bellissima esperienza. Grazie per la gentilezza”

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11.EXCLUSIVE – Wine Tasting near Florence with Castle and Ancient Cellars Tour

★★★★★★★★★★5.0 · 34 reviews · from $81

You’ll tour the still-inhabited Castello del Trebbio near Pontassieve with a professional guide, visit its old wine cellars, and taste four estate wines with Tuscan snacks. The small group, usually capped at eight, keeps the castle visit personal. You can also add a Tuscan dinner or arrange an eight-seat van from Florence.

“Best thing we did in Florence! Beautiful setting, great historic stories, wine and olive oil deliciousness. Would recommend to all for a relaxing, gorgeous afternoon! We want to come back and stay in a guest house!”

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12.Florence: Exclusive Chianti Wine Tour at 3 Wineries & Lunch

★★★★★★★★★★4.8 · 21 reviews · from $225

Spend seven hours in Chianti with an English or Italian guide such as Giovanni, Andrea, or Cosimo. Visit three family-run wineries, taste Chianti and other Tuscan wines, sample olive oil, explore Impruneta and medieval cellars, and enjoy a multi-course farm lunch.

“With so many wine tours in Florence, this one truly stands out! The guide was fantastic, the van was comfy, and the itinerary was carefully planned. We wanted a tour with three wineries, and luckily, we found this one, making it a must! I met wonderful people, tasted incredible wines and learned a lot from passionate winemakers. Highly recommended.”

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13.Chianti: Premium Wine, Olive Oil and Vinegar Tasting

★★★★★★★★★★4.8 · 19 reviews · from $36

At Poggio ai Laghi, a wine expert guides you through six wines, three olive oils, two balsamic vinegars, and Tuscan appetizers. Expect art and winemaking history in a private tasting setting, with English, French, Spanish, and German assistance available.

“The guide provided excellent attention and explanations. The facilities are very good.”

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14.Half Day Chianti Wine Tour with Private Luxury Van

★★★★★★★★★★5.0 · 17 reviews · 5 hours (approx.)

Leave Florence at 10 a.m. in a private luxury van with an English-speaking driver, then visit Greve, Montefioralle, and Casa Emma. You can add a winery lunch or tasting, enjoy Chianti Classico, and stop for photos along the countryside roads. Drivers may include Michele, Marco, Alessandro, or Simone.

“My husband and I had the pleasure of having Mike (Michele) for our tour and cannot express enough how fabulous our day was! He brought us to two incredible wineries that showed us impeccable attention and the wines at both Casa Emma and Corbucci were very good and our lunch at Corbucci was wonderful! We loved hearing about the countryside and history from Mike. He was an excellent guide and made for a very memorable day for us. I would definitely recommend Mike and this tour as you get a very personalized experience.”

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15.Syracuse: Exclusive Sicilian Wine Tasting Experience

★★★★★★★★★★5.0 · 15 reviews · 1.5 hours · from $81

Visit Azienda Agricola Pupillo outside Syracuse for a 90-minute small-group tasting led in English or Italian. Walk through the centuries-old estate, Greek fortress, winery, vineyards, and exotic garden, then sample four Sicilian wines including Nero d’Avola and Cabernet. Guides such as Julia add a warm, personal touch.

“We thoroughly enjoyed our visit. The botanical Gardens, surroundings and scenery are beautiful. Our guide Julia was brilliant. Informative and funny. The wines are delicious. The food was fantastic. Would highly recommend!”

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