Long Island Winery Tour: Private Tastings at Osprey & Duck Walk

Wine tastings happen with a view of the vineyards you're tasting from.

A private Long Island winery tour picks you up from your address and takes you to Osprey and Duck Walk for 3–5 wine tasting flights at each stop, with live music on weekends and lawn seating overlooking the vines. The tour runs 5 to 6 hours and includes all fees, taxes and transportation in a sedan or SUV. You can bring your own lunch or buy light fare at Osprey.

Step-by-step itinerary

Wine tastings and vineyard relaxation

• Pickup from Long Island address
• Enjoy 3-5 wine tasting flights at Osprey
• Relax on lawn with lunch and live music
• Visit Duck Walk for 3-5 wine tasting flights
• Enjoy live music at Duck Walk

The experience

Osprey and Duck Walk sit on opposite ends of Long Island's wine country, each with sprawling vineyards visible from the tasting room. The route starts with private pickup from any Long Island address (though locations in Nassau County will add travel time), and moves between the two wineries at a pace that leaves room to linger. You taste 3–5 flights of local wine at each stop, meaning you're sampling the same producers twice over, which lets you compare how different vineyards handle the same grapes.

Both wineries have lawn seating that overlooks the vines, so lunch (whether you bring it or buy it at Osprey) happens with the view that made you want to come. Weekends bring live music to the grounds, turning the afternoon into something closer to a garden party than a structured tour. The sedan or SUV keeps the group small and comfortable, and because pickup happens from your own address, there's no meeting point to find or early arrival to plan.

You choose between two options at checkout: the Classic Two Winery Tour hits both Osprey and Duck Walk with tastings and live music included, or the A La Carte Wine Tour lets you shape the day differently. Either way, all fees and taxes are built into the price, so nothing surprises you at the register.

What’s included

• Private pickup from any Long Island address in a sedan or SUV.
• wine tastings (3–5 flights at each winery).
• live music on weekends.
• lawn seating with vineyard views.
• all fees and taxes.

Options for this experience

2 options

Wine Tour A La Carte11:00, 11:30 and 12:00Tastings are not included. Duration is four hours from pickup to dropoff. You can direct the vehicle to whichever wineries you like. Pickup is included.

Two Winery Classic Tour11:00, 11:30 and 12:00Tastings are included. Duration is five hours from pickup to dropoff. For lunch, you can bring your own to enjoy at Osprey Vineyard or purchase a light lunch there as an add-on. Pickup is included.

You'll see the exact price of each option when you check availability.See dates and prices

Before you book

Days and timesEvery dayDepartures at 11:00, 11:30 and 12:00

Book up to4h before

GroupPrivate

Meeting point and pickupHotel pickup included.

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.

Prices and times updated 9 days ago

Good to know

Low physical effortStroller-friendlyPets welcomePublic transport nearby

Operated by Winston Wine Tours

Is this one for you?Choose the Classic Two Winery Tour if you want both Osprey and Duck Walk in one afternoon with the full tasting experience at each. The A La Carte option gives you flexibility to shape the day around which winery or which wines matter most to you.

Traveler reviews

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Top questions

Can I bring my own food to the Long Island wineries?

Yes. You're welcome to bring your own lunch to enjoy on the lawn at either winery, or you can buy a light lunch at Osprey if you prefer not to pack.

What's included in the private pickup on this Long Island winery tour?

Private pickup from any address on Long Island is included, along with transportation in a sedan or SUV between the wineries. All fees and taxes are also included in the price. The driver is separate.

Do the wineries have live music every day?

Live music happens on weekends at both Osprey and Duck Walk, adding to the lawn experience while you taste.

How much wine do I taste at each winery?

You taste 3–5 wine tasting flights of local Long Island wine at each stop, so you're sampling multiple producers and styles across the afternoon.

How long does the whole tour take?

The tour runs 5 to 6 hours total, including pickup, travel between the two wineries, and time to taste and eat at each location.