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304 North Cardinal St.
Dorchester Center, MA 02124
Discover Long Island's top vineyards with a private tour featuring tastings, live music, and scenic views—perfect for wine lovers and celebrations alike.
When it comes to enjoying a day among Long Island’s celebrated wineries, this private tour promises a blend of scenic beauty, delicious wines, and the convenience of door-to-door transportation. With an estimated duration of 4 to 6 hours, it offers a leisurely way to explore some of the region’s most popular vineyards without the hassle of driving. The tour includes visits to Osprey’s Dominion Vineyards and Duck Walk Vineyards North — two spots renowned for their quality wines and inviting atmospheres.
What we really like about this experience is the flexibility it offers. You can choose to include tastings in your package or simply book transportation and curate your own tasting journey at your own pace. Plus, the tour’s private setting means you won’t be stuck with a large group — perfect for celebrations like birthdays or bachelorette parties. On the flip side, some guests mention the cost relative to the number of tastings, which is worth considering if you’re on a budget. This tour suits wine lovers eager for a relaxed, personalized experience with the bonus of live music and stunning vineyard views.
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The tour opens with a pick-up at your preferred location on Long Island, where a private sedan or SUV awaits to whisk you away on a wine adventure. The itinerary primarily revolves around two key stops: Osprey’s Dominion Vineyards and Duck Walk Vineyards North. These are some of the most loved spots in the region, known for their sprawling vineyards and welcoming atmospheres.
This first stop is a highlight. You’ll enjoy 3-5 wine tasting flights, which means plenty of opportunities to sample different varieties. Osprey’s Dominion is famous for its beautiful, sprawling lawns that overlook the vineyards — perfect for relaxing with a glass in hand. Expect to enjoy not just the wines but also the live music that often accompanies weekend visits. Guests have mentioned that the tasting flights are included in the admission, and some reviews note that the experience is quite scenic and peaceful, especially if you pack a picnic lunch to enjoy on the lawn.
One reviewer, Virginia, noted, “The wineries were nice, spending time with friends was great but it was way too expensive for the number of wineries and tastings.” This suggests that while the experience is delightful, the overall value depends on how many tastings you indulge in and your budget. Still, the setting and quality of wines tend to impress most visitors.
The second stop is Duck Walk Vineyards North, which is available if you opt for the full two-vineyard experience. Here, you’ll also enjoy 3-5 wine flights, with the added perk of live music that enhances the relaxed, festive vibe. Keep in mind that admission isn’t included here, so you’ll need to purchase tastings separately if you choose this option. Reviewers have appreciated the choice of wineries, noting that the quality wines and welcoming staff make this stop worth the visit.
A guest, Courtney, shared, “Anna, our driver, was a lot of fun and entertaining. The wineries they chose were perfect!” This indicates that the driver’s personality adds a lot to the day, making it both fun and personal.
Throughout the tour, guests can expect well-paced visits, with about an hour at each vineyard. The private setting means the driver is available for questions or recommendations, and most importantly, you can relax without worrying about transportation logistics.
The live music, often enjoyed during tastings, adds an unhurried, festive vibe that elevates the experience. Some reviews mention that the scenery and the wines themselves are the main draws, with the opportunity to enjoy a laid-back day in a beautiful setting.
For $100 per person, this tour offers good value if you’re keen on a personalized, hassle-free way to sample Long Island wines. The price includes all fees and taxes, along with private pickup and drop-off at your accommodation or other designated location on Long Island. Keep in mind, gratuities aren’t included, so if you enjoy your driver’s service, tipping is appreciated.
Transportation is in a comfortable sedan or SUV, ideal for small groups. The tour is limited to your party only, making it a private affair — perfect for celebrating special occasions or just enjoying a day with friends.
While some reviews point out that the tastings are modest in number (3-5 flights per winery), the overall package offers convenience, comfort, and a personalized touch that many travelers find worth the price. The scenic views, live music, and the opportunity to curate your own tasting experience (if you prefer to skip included tastings) make it versatile.
Most bookings are made about three weeks in advance, reflecting its popularity. The tour offers a free cancellation policy up to 24 hours before the scheduled start, providing flexibility for planning or weather changes.
This experience is ideal for wine enthusiasts wanting a relaxed, private day among Long Island’s vineyards. It’s especially suited for celebration groups like birthdays or bachelorette parties looking for a memorable, fun-filled outing. If you value comfort, flexibility, and scenic vineyard settings, you’ll likely enjoy this tour. However, if you’re budget-conscious and prefer sampling as many wines as possible, you might find the tastings somewhat limited for the price.
The Long Island Winery Tour delivered by Winston Wine Tours offers a well-rounded, enjoyable way to explore the region’s vineyards without the stress of driving. The combination of beautiful scenery, live music, and personalized service makes it stand out from more generic wine tours. The ability to choose your start time and tasting options makes it flexible to fit your plans.
While some might wish for more tastings for the price, the overall experience—especially if you’re celebrating or seeking a relaxed day—can be quite rewarding. You’ll love the views, the wines, and the chance to spend quality time in a scenic setting. Just remember to book ahead and plan your day around the vineyards’ offerings and your own wine preferences.
Is pickup included in the tour?
Yes, private pickup anywhere on Long Island is included in the price, ensuring a seamless start to your day.
Can I choose to just book transportation?
Absolutely. You can opt for just the transportation and then select your tastings independently at each vineyard.
How long does the tour last?
The tour lasts approximately 4 to 6 hours, giving you plenty of time to relax and enjoy each stop.
Are there any age restrictions?
Most travelers can participate, and service animals are allowed. However, since it involves alcohol tasting, minors are not permitted to partake in tastings.
Are the vineyards flexible about changing based on availability?
Yes, winery selections may change due to availability, so it’s best to confirm closer to your booking date.
What’s included in the price?
All fees, taxes, wine tastings (if you choose to include them), and private transportation are included.
How do I pay for tastings not included?
You will pay separately at each vineyard for tastings, which vary in cost.
Can I cancel the tour if my plans change?
Yes, cancellations are free if made at least 24 hours in advance.
Is live music available during the tastings?
Yes, live music is often part of the experience at the vineyards, adding a lively atmosphere.
What should I bring for the tour?
Comfortable clothing, sun protection, a camera, and any snacks or picnic items you’d like to enjoy on the lawn.
In summary, the Long Island Winery Tour offers a personally tailored way to taste the best of Long Island’s vineyards in comfort and style. Whether you’re celebrating a special day or simply seeking a relaxing escape in wine country, this tour provides a scenic, enjoyable experience worth considering.