Romantic Champagne Sunset Sailing Tour | Long Island Yacht Cruise from Shelter Island & Greenport
This is the newest top-rated Sailing Tours Long Island couples and visitors choose for romantic evenings on the water.
As the sun sinks low over Peconic Bay, casting a warm glow across the water, SailSelinaNY’s Champagne Sunset Sail invites you to unwind aboard a piece of Greenport history. Feel the soft evening breeze, hear the sails fill, and savor your favorite bottle of wine or bubbly as the sky glows gold and rose around you. Each moment aboard our lovingly restored Greenport-built family yacht is a celebration of the good life—relaxed, refined, and undeniably romantic.
Onboard your East End Sunset Champagne Cruise
Duration
~2 hours (timed for sunset)
Vibe
Relaxed, scenic, and romantic—perfect for date night or a special celebration
Capacity
Small group, max 6 guests (private charters available)
Sit back and savor—or help the crew raise sail if you’d like
Participation
Departing Shelter Island sailing from Dering Harbor
Departing Greenport sailing from Mitchell’s Park
Sail past the shores of the East End of Long Island’s North Fork
Sweeping sunset views
Osprey nests, classic cedar-shingled homes, and ferry crossings
A front-row seat to the color show—every night is a little different
Scenic Route Highlights – Greenport & Shelter Island
Whether for a date night or a spontaneous getaway, a sunset sail on Shelter Island offers the most scenic views and peaceful evening atmosphere on Long Island’s East End.
Good to Know Before You Sail
Dress in light layers (sun can linger, breezes cool quickly after dusk)
Soft, non-marking shoes recommended
BYO small snacks welcome (please, no messy foods)
Weather/sea conditions may adjust our exact course—your comfort comes first
Great addition to your Hamptons Day Trip
Join us for a 2-hour evening sail departing from Shelter Island’s Dering Harbor or Greenport Village. Glide past cedar-shingled homes, watch ospreys circle their nests, and see the North Fork shoreline sparkle as twilight settles in. With a maximum of six guests, our intimate setting ensures personalized attention and a peaceful atmosphere—perfect for couples and close friends.
This Champagne Sunset Sail is a perfect centerpiece for a romantic Long Island getaway, blending classic yacht elegance with the soft glow of an East End sunset.
Many guests tell us that, of all the Long Island sailing tours they’ve tried, this Champagne Sunset Sail is the most romantic, thanks to the classic yacht, small-group setting, and golden-hour views over Peconic Bay.
Romantic Long Island Sunset Cruise
What to Expect - Relaxation, Romance & VIP Service on the Water
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Our lovingly preserved 1926 catboat offers a luxurious, comfortable sail. Guests consistently praise her pristine condition and classic beauty.
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Our welcoming crew enhances every trip with local knowledge, sailing expertise, and personal hospitality.
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What began as a passion project has evolved into something more. We’re proud of where we’ve been and even more excited for what’s ahead. What sets us apart isn’t just our process—it’s the intention behind it. We take time to understand, explore, and create with purpose at every turn.
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Hear fascinating tales of Greenport’s shipyards, Shelter Island’s history, and the North Fork’s deep sailing legacy.
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Sailing with us helps preserve a living maritime treasure—a one-of-a-kind link to Long Island’s yachting past.
Guests often tell us this feels like one of the best boat tours on Long Island, thanks to the small-group setting, historic yacht, and personalized storytelling on every sail. As one of the top Shelter Island yacht charters, SailSelinaNY offers a unique experience aboard a fully restored 1926 wooden yacht – perfect for families, couples, or friends looking for a classic sailing adventure.