When it comes to wine country experiences, Long Island has been steadily gaining recognition, and a private winery tour like this can be a fantastic way to spend a day. We’ve looked into the Long Island Winery Tour offered by Winston Wine Tours, and while we haven’t personally taken it, the details and reviews paint a pretty clear picture of what to expect. Whether you’re celebrating a birthday, planning a bachelorette outing, or just want a relaxed day tasting local wines, this tour offers a convenient way to explore some of Long Island’s best vineyards.
Two things we really like about this tour are the private transportation—which means you’re not stuck in a crowded bus—and the flexibility to choose your start time and tastings. Plus, the inclusion of live music at some stops adds a fun, festive touch. On the flip side, a potential consideration is the cost relative to the number of tastings offered at some wineries. That might give some folks pause, especially if you’re a wine enthusiast who expects a lot for the price.
This tour seems best suited for those who want a comfortable, guided experience with a touch of personalization—perfect for special occasions or a low-stress day exploring Long Island’s vineyards. If you value a relaxed, private setting and enjoy some live music with your wine, this could be just right.
Key Points
- Private transportation ensures a comfortable and stress-free journey around the vineyards.
- You can customize your experience by choosing to include tastings or just transportation.
- The tour includes stops at popular vineyards like Osprey’s Dominion and Duck Walk Vineyards.
- Live music at the vineyards adds a lively, enjoyable atmosphere.
- The tour is well-booked in advance, with an average booking window of 23 days.
- The experience is quite flexible, with a duration of about 4 to 6 hours, making it perfect for a half-day adventure.
What You Can Expect From the Tour
The Long Island Winery Tour is designed to be a relaxed, enjoyable way to sample some of the region’s best wines without the hassle of planning transportation or driving yourself. The tour offers a private pickup from anywhere on Long Island, meaning you can start your day from your hotel, home, or a favorite spot. The vehicle—either a sedan or SUV—keeps you comfortable, especially if you’re traveling with friends or a small group.
Planning more time in Long Island? We've covered other experiences worth considering.
Itinerary Breakdown
Stop 1: Osprey’s Dominion Vineyards
Your first stop is at Osprey’s Dominion Vineyards, a well-loved vineyard known for its sprawling lawns and stunning views. Expect to sample 3-5 wine flights of Long Island wines—think crisp whites, smooth reds, or maybe a sparkling or two. The admission ticket is included with your booking, and you’ll have about an hour here to savor the wines, enjoy a picnic lunch on the lawn, and listen to live music if it’s scheduled. This stop really sets a relaxed, scenic tone for the day.
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 the number of tastings.” That’s worth keeping in mind—while the experience is enjoyable, the wine tastings at the vineyards themselves seem somewhat limited in number, especially considering the overall cost.
Stop 2: Duck Walk Vineyards North
The second stop is at Duck Walk Vineyards North (but only if you opt for the two-vineyard package). Here you’ll again enjoy 3-5 tasting flights of local wines and live music. This stop’s admission isn’t included in the base price, so you’ll need to pay for tastings if you choose to do this part of the tour. The reviews from past guests, like Courtney, describe it as a perfect addition: “Anna, our driver, was a lot of fun and entertaining,” and the visit was ideal for celebrating special occasions like birthdays.
What’s Included & What’s Not
The price includes all fees and taxes, your wine tastings at the vineyard(s), live music, and private pickup. The main extra cost is driver gratuity, which is customary but worth planning for. The flexibility to add or skip tastings gives you some control over the experience—if you’re more interested in sightseeing and a relaxed vibe, you could just enjoy the scenery and music, and handle tastings separately.
Duration and Booking
The tour runs between 4 to 6 hours, which makes it a perfect half-day activity. It’s a popular choice, often booked about 23 days in advance, so plan ahead if you want to secure your preferred start time.
The Experience for Different Types of Travelers
This tour is particularly appealing if you’re looking for a stress-free, personalized day with friends or family. It works well for celebrating birthdays, as Courtney’s review highlights, or for a bachelorette party, thanks to the private nature and flexible scheduling. However, if you’re seeking a more extensive wine-tasting experience with numerous wineries in one day, this might feel a bit limited, especially considering the tasting costs at some vineyards.
What we love is the scenic setting and the chance to enjoy some live music while sampling wines. Many reviews speak positively about the friendliness of the driver, Tom or Keith, who help make the day enjoyable and relaxed. Plus, the fact that this is a private tour means you won’t have to contend with strangers, which adds a personal touch.
A Closer Look at the Itinerary
The first winery, Osprey’s Dominion, offers a pretty memorable start. Known for its expansive lawns and vineyard views, it’s a picture-perfect spot for a picnic or just soaking in the scenery. The wine flights here are considered a highlight, and the inclusion of live music creates a lively, fun environment. You’ll have about an hour here, enough time to taste, chat, and take some photos.
The second stop, Duck Walk Vineyards, adds another layer of enjoyment. Its reputation for top-notch wines and the lively atmosphere with music make it a natural follow-up. The tastings at this vineyard give you an opportunity to explore different styles, assuming you decide to include this stop.
Authentic Guest Perspectives
Virginia’s review notes that the wineries were nice and that spending time with friends made the experience special, but she also pointed out that it felt somewhat costly considering the number of tastings included in the tour. This highlights a key point: if you’re a dedicated wine enthusiast, you might find the tastings at each vineyard somewhat limited for the price. However, the quality of the wines and the scenic environment seem to compensate for that.
Courtney’s experience, on the other hand, emphasizes how well the tour is curated for celebrations. “Anna, our driver, was a lot of fun and entertaining,” and she describes the wineries as perfect for special occasions, which is a good sign that this experience is more than just about the wines—it’s about creating memories.
Pricing and Value Considerations
At $100 per person, the tour isn’t the cheapest option out there, but it does include a fair amount of value—private transportation, at least one winery visit with tastings included, and live music. Still, the cost of tastings at the vineyards themselves can add up if you choose to indulge at both stops.
The ability to book the transportation only and then select your tastings separately might be a good option if you’re budget-conscious or prefer more control over your wine sampling. Keep in mind, if you’re someone who appreciates more tastings per visit, this might feel a bit limited unless you’re willing to pay extra at each vineyard.
The Booking & Cancellation Policy
The tour is booked comfortably in advance, and the process seems straightforward with confirmation received at booking. The free cancellation policy offers peace of mind—you can cancel up to 24 hours before the tour for a full refund, which is pretty generous and helpful if your plans change unexpectedly.
Who Would Love This Tour?
This experience is ideal for small groups or couples looking for a private, relaxed day exploring Long Island’s wineries. It’s perfect for special occasions, especially birthdays or bachelorette parties, thanks to the personalized touch and the festive atmosphere created by live music. If you prefer a quieter, more intimate experience with the flexibility to choose your tastings, this tour fits the bill.
However, if you’re someone who wants to visit many wineries in a day or expects a large tasting variety, you might find this a bit lacking in quantity, and you may want to supplement it with additional tastings or visits.
The Sum Up
All in all, the Long Island Winery Tour offers a comfortable, personalized, and scenic way to enjoy the region’s wines without the stress of driving. The inclusion of live music, the flexibility to customize your experience, and the private transportation make it a strong option for celebrating special occasions or simply indulging in a relaxing day with friends.
While some may find the number of tastings at the wineries a bit limited relative to the cost, the quality of the experience—great views, friendly guides, and enjoyable wines—can make it feel well worth it. If you’re after a laid-back, intimate tour that focuses on quality over quantity, this might be your ideal Long Island wine adventure.
Long Island Winery Tour
“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. Fo…”
FAQs
Is this tour suitable for groups of any size?
This is a private tour, so only your group will participate. It’s perfect for small gatherings, couples, or families looking for a tailored experience.
Can I choose my start time?
Yes, you can select your preferred start time when booking, giving you flexibility to fit the tour into your schedule.
What’s included in the price?
The tour price covers private pickup, all fees and taxes, wine tastings at the vineyard(s), and live music during stops. Driver gratuity isn’t included.
Can I just book transportation and handle tastings myself?
Absolutely. You can opt for just the transportation service and then choose and pay for tastings separately at each vineyard.
How long does the tour last?
The tour typically lasts between 4 and 6 hours, perfect for a half-day trip.
Are the vineyards accessible with public transportation?
Yes, the tour offers pickup near public transportation, although the focus is on private transport for comfort.
Is this experience family-friendly?
Since it involves wine tastings and live music, it’s better suited for adults. Service animals are allowed if needed.
What if I need to cancel?
You can cancel up to 24 hours in advance for a full refund. Cancellations within 24 hours are not refunded.
How far in advance should I book?
Most travelers book about three weeks ahead, but booking earlier is recommended for peak seasons or weekends.
Whether you’re after a relaxing day among vineyards or celebrating a special event, this tour offers a solid option. Just come with an open mind, a sense of adventure, and maybe a few extra dollars for tastings if you’re keen to indulge more.
