The 14 Best Long Island Wine Tours

1.Long Island Wine and Food Day Trip with Sommelier host from NYC

★★★★★★★★★★4.5 · 53 reviews · 9 hours (approx.) · from $148Our pick

Leave Manhattan at 9 a.m. for a full-day North Fork wine outing with a certified sommelier, air-conditioned transport, tastings at two rotating wineries, and a locally sourced sandwich lunch. Pellegrini Vineyards and RGNY are among the possible stops. Expect about 90 minutes at each winery, a group of up to 48, and a return to the Midtown meeting point.

“This tour was AMAZING I will definitely do it again or some of his other tours! Tour guide was VERY knowledgeable. Bring your own lunch though there was limited food available.”

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2.Mattituck New York Guided Farm and Wine Country Bike Tour

★★★★★★★★★★5.0 · 43 reviews · from $139Top rated

Spend about five and a half hours cycling Mattituck with a guide, stopping at two vineyards, a beach for olive oil and vinegar tastings, and a longtime farm stand. Mike and Nicole are among the guides who have led the tour. Bikes, helmets, water, refreshments and downloadable photos are included; wine costs extra.

“This was an excellent tour. Our tour guides were extremely efficient, friendly and keep us motivated to stay in course and keep up with the riding. We made 2 winery stops, a stop at the beach, and a stop to a local popular bakery. A car fRead more”

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3.Long Island Sommelier-Guided Wine Tasting Tour

★★★★★★★★★★4.8 · 27 reviews · 9 hours · from $159

Ride from Midtown Manhattan to Long Island’s North Fork for two winery visits, private tastings of four wines, vineyard walks, and a farm-market stop. Your English-speaking sommelier guide leads the day, with past tours led by guides including Steve, Sam, and Tim. A locally sourced lunch is served with the first tasting.

“The trip was great. The bus was clean and even had assigned seating. Tim was a great guide. The lunch was labeled so you were guaranteed to have your selection. The various wines were good. Overall, it was a great experience.”

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4.Tour and Tasting at Brooklyn Winery

★★★★★★★★★★4.7 · 22 reviews · 1 hour · from $45Best value

Join a wine educator at Brooklyn Winery in Williamsburg for a one-hour look at a real, working winery and a guided tasting of five wines made on site. Guides Kirsten and Max have led engaging sessions, though your guide may vary. Afterward, stay for food and more wine, or head out to explore the neighborhood.

“We had a fantastic time with Kirsten - she was knowledgable, friendly, and gave us a special treat to try on the day. Thank you!”

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5.Mattituck Bike Wine Country and Fruit Orchard Tour

★★★★★★★★★★5.0 · 15 reviews · from $141

Ride 13.5 miles with a guide through Mattituck’s vineyards and farmland, stopping for olive oil and vinegar tastings, Peconic Bay views, a farm stand, and a fruit orchard. Hybrid and tandem bikes, helmets, refreshments, guide photos, and a support vehicle are included. Wine tastings and fruit picking cost extra.

“This was a superbly organised tour with very qualified and competent guide tours. Safety was always paramount as was our comfort. The buffet lunch was amazingly tasty and included many vegetarian options. The rest was all super hRead more”

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6.Guided Farm and Wine Country Bike Tour in Mattituck NY

★★★★★★★★★★5.0 · 15 reviews · from $132

Ride a single or tandem hybrid bike through Mattituck, New Suffolk, Cutchogue and Jamesport with East End Bike Tours. Expect vineyard gardens, a Peconic Bay beach, a farm stand, herb-infused oil and vinegar tastings, and a small-group pace. Wine and lunch cost extra. E-bikes may be reserved as a limited add-on.

“What a memorable experience! Everthing was well planned and the day was so enjoyable. Wineries we visited were terrific. Highly recommend for family or friends.”

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7.Private Guided Wine Country Bike Tour in Mattituck

★★★★★★★★★★5.0 · 15 reviews · from $199

Ride Mattituck’s mostly flat backroads with a private guide, choosing a 12, 14.5, 16, or 19-mile route. Stops may include the Peconic Bay, Crushed Olive, a boutique vineyard, and Wickham’s Fruit Farm. Your group chooses two tasting experiences together. Hybrid bikes, helmets, chilled water, photos, and a support vehicle are included.

“We booked private guided tour, the guide was friendly and staff of east end bike tour accomodating.. easy to booking and fast.”

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8.Vintage Wine Tasting and Classic Car Combo Tour

★★★★★★★★★★3.4 · 6 reviews · 2 hours · from $175

Start at Central Park Cafe for a bartender-led tasting, then take in Midtown Manhattan from a chauffeured vintage car. Expect three glasses per person, stories about New York’s Prohibition era, and a private group of up to 10. The wine selection and session format can vary, so ask what is being served before you book.

“Excellent friendly service. Loved the vintage car vibe and very unique Georgian wine. To improve-Pick up info and prep on the wine you are presenting. Great experience. Excellent event for after work drinks. They include a pizza and offer dinner menu discounts which are not advertised. This added to our experience”

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9.Hudson Valley Wine Tour: NY’s only sommelier-guided tour!

★★★★★★★★★★4.4 · 5 reviews · 9 hours · from $159

Ride from Midtown Manhattan to two Hudson Valley wineries for private tastings, vineyard walks, and winemaking explanations with an English-speaking sommelier guide. The day also includes local food samples and a 30-minute stop at a farmers market. Guides Sam and Steve have both been named on past tours, though your guide may vary.

“Muy buena. La explicación del guía (Sam) fue entretenida y nos ayudó a entender y aprender algunas características de las uvas y viñedos de la zona. El conductor fue correcto, y la partida y llegada fueron en los tiempos definidos.”

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10.Long Island Winery Tour

★★★★★★★★★★4.5 · 5 reviews · 5 to 6 hours (approx.) · from $295

Spend about five to six hours visiting Long Island wineries in a private sedan or SUV, with pickup from an address on Long Island. The planned stops are Osprey’s Dominion Vineyards and Duck Walk Vineyards North, each with tastings and live music. Lunch is extra unless you choose the lunch upgrade. Drivers on past outings have included Keith, Anna, and Tom.

“The wineries were nice, spending time with friends was great but it was way too expensive for the number of wineries and the number of tastings. For instance Osprey offered 3 tastings for $10 and 5 for $15. Considering the price of the tour, I think it would have been appropriate for Winston to purchase the 5 tastings. Keith, the driver, was great!”

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11.Long Island Wine Tour North Fork Sights Bites Flights Half Day AM

★★★★★★★★★★5.0 · 5 reviews · 4 to 5 hours (approx.) · from $339

Spend four to five hours with local guide Eric on a private North Fork outing from Mattituck to Greenport. Your plans can include wineries, an oyster farm, a chocolatier, small plates, shops, and the Greenport maritime museum. East End pickup, food, drinks, and transport are included; winery visits depend on your preferences.

“Working with Eric was seamless from start to finish. He’s professional, friendly, and truly looks out for his guests. Eric meticulously planned an incredible oyster farm tour where we learned the process firsthand and enjoyed the freshest farm-to-table oysters. It was the highlight that set the tone for a perfect day. He made my friend’s bachelorette weekend an absolute hit, made me look like a fabulous hero, and even helped capture great group photos throughout the day. As a passionate local and true North Fork insider, Eric curated the best of the region with beautiful wineries, hidden gems, local bites, and special surprises like Bobby Flay’s world-famous meatballs. From flowers…”

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12.Private Luxury Wine Tours of Long Island Pindar Winery

★★★★★★★★★★5.0 · 5 reviews · 6 to 7 hours (approx.) · from $180

This six-to-seven-hour private tour starts and ends at the Long Island Rail Road station in Hicksville. Visit Pindar Vineyards, Raphael Winery, and Lenz Winery with private transport and six wine tastings included. Nancy has led tastings at Pindar, and Manpreet has driven the route. Meals and purchases beyond the included tastings cost extra.

“Our trip was absolutely refreshing and unforgettable. From the moment we set off, everything was perfectly organized smooth transport, warm hospitality, and a well-planned itinerary that balanced relaxation with adventure.”

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13.Martha’s Vineyard & Essex 2-Day Tour from New York | Kids 50% Off

★★★★★★★★★★5.0 · 3 reviews · 2 days (approx.) · from $478

Leave New York at 6:30 am for a two-day trip to Connecticut, Newport, and Martha’s Vineyard. A bilingual guide-driver handles the transport, with one hotel night and breakfast included. Depending on your package, add the Essex steam train and riverboat, the Breakers, and the island ferry. Expect a narrated Vineyard tour and two hours of free time.

“The tour is wonderful! It is very relaxing but have lots of entertainments. It is also very well organized. The steam train and river boat was just a fantastic adventure. We also enjoyed very much visiting the Breakers cottages, it really looks like Renaissance luxury cottages. And Martha's Vineyard Island is beautiful, wonderful beaches and relaxing atmosphere.”

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14.Long Island Wine Tour North Fork Sights, Bites & Flights Full-Day

★★★★★★★★★★5.0 · 3 reviews · 7 to 8 hours (approx.) · from $559

Spend about 7 to 8 hours exploring the North Fork with Eric, your private guide and driver. The route can include wineries, an oyster farm, a chocolatier, local food stops, specialty shops, and a Greenport history walk. Pickup is available across Long Island’s East End, and the day is shaped around your interests.

“What a great day! Thanks to Eric we had such a nice time exploring the North Fork wine country. Just beautiful!!!! Two wine stops, a brewery, a chocolatier, street fair for local shopping, lunch and dinner bites. We sure covered lot of territory! Eric definitely catered the day to our interests. Light, fun and interesting. I highly recommend the tour!!!”

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