Wine Tours on Long Island
There’s no better way to spend a day on the North Fork than with a glass of wine in hand, surrounded by good company and great views. Whether you’re celebrating a birthday, planning a getaway with friends, or just looking for an easy escape from the city, Winston Transportation offers private wine tours that bring you to the heart of Long Island’s wine country—without the hassle of driving or coordinating logistics. Let us handle the ride, while you focus on the pour.
Luxury Sedans
Luxury Black Sedan (up to 3 guests)
Luxury SUVs
Luxury Black SUVs (up to 6 guests)
Executive Vans
11 or 14 Passenger Executive Vans for Small Group Transportation
Mini Bus & Motor Coach Buses
24 – 55 Passengers for Large Groups
Your Day in Wine Country
Our private tours are built around comfort, flexibility, and a premium experience. Most wine tours last 4–5 hours, depending on pickup location and itinerary. You’ll be matched with a professional chauffeur and a well-appointed vehicle that fits your group—typically an SUV or executive van for groups of 2 to 7 passengers. We also have sedans, minibuses, and full-size coaches available for larger parties.
Sample Wine Tour Itinerary
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11:00 AM – Pickup at your location anywhere on Long Island
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12:00 PM – Optional stop to pick up lunch (add-on available for $25/person)
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12:15 PM – Tastings at Osprey’s Dominion Vineyard
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1:45 PM – Tastings at Duck Walk Vineyards (Classic Tour only)
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3:30 PM – Optional visit to Briermere Farmstand & Bakery
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4:00 PM – Return drop-off
Every tour can be customized to suit your preferences. Want to swap in another vineyard? Add a stop for a second tasting flight? Just let us know. We’re happy to create a route that fits your group’s vibe.
Choose Your Wine Tour
We offer three tour packages for small groups. Each includes your private chauffeured vehicle and door-to-door service. Tastings and time allowances vary by package.
Economy Wine Tour
Transportation Only
Includes 4 hours of vehicle time. You choose the stops, and pay for your tastings directly at each winery.
Pricing (plus tax & gratuity):
- 2 passengers: $185 per person
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3 passengers: $125 per person
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4 passengers: $95 per person
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5 passengers: $75 per person
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6 passengers: $65 per person
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7 passengers: $55 per person
Add lunch to any tour for $25 per person.
Value Wine Tour
One Winery, Tasting Included
Includes door-to-door service, 4 hours of vehicle time, and tastings at Osprey’s Dominion Vineyard.
Pricing (plus tax & gratuity):
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2 passengers: $210 per person
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3 passengers: $150 per person
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4 passengers: $120 per person
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5 passengers: $100 per person
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6 passengers: $90 per person
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7 passengers: $80 per person
Add lunch to any tour for $25 per person.
Classic Wine Tour
Two Wineries, Tastings Included
Our most popular option. Includes tastings at Osprey’s Dominion and Duck Walk Vineyards, plus 5 hours of total time
Pricing (plus tax & gratuity):
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2 passengers: $280 per person
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3 passengers: $205 per person
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4 passengers: $165 per person
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5 passengers: $145 per person
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6 passengers: $130 per person
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7 passengers: $120 per person
Add lunch to any tour for $25 per person.
Make It Your Own
Every group is different. Some want music and mimosas on the way out, others want a low-key ride through the countryside. Whether you’re planning a birthday, bachelorette, anniversary, or just a weekend away, we can help design a wine tour that matches your style and budget.
We pick up anywhere on Long Island and can accommodate most custom requests. If you have more than 7 guests, or want help selecting wineries, reach out—we’ll walk you through the options.
Over 500 Tours and Counting
With over a decade of experience and more than 500 wine tours completed, Winston Transportation is a trusted name in private group transportation. Our drivers are professional, courteous, and know the back roads of the North Fork like locals. We know how to plan a day that flows smoothly—from the first pickup to the last drop-off.
We’re proud to be offering our 2025 Wine Tour Season to returning guests and new faces alike. Tours fill up quickly during spring and summer, so we recommend booking early.
Ready to plan your Long Island wine tour?
Call us today for availability and custom quote requests.