Classic Sailing Charters on Long Island’s East End

Private yacht sails from Greenport & Shelter Island aboard a 1926 Wooden Yacht

Limited to just 6 guests for the most intimate sailing experience on the water.

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Celebrating 100 Years

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Celebrating 100 Years ✳︎

A Different Kind of Long Island Sailing Experience

Escape the crowds and discover a waterfront adventure that feels timeless, romantic, and uniquely yours.

Why Sail Salina NY?

  • Vintage Photo of Sail Selina II from 1926. Showcasing the age of this historic ship.

    Built in Greenport in 1926

    Authentic maritime heritage

  • Beautiful sunset photo of Sail Selina II. Showcases what your cruise aboard this historic ship could look like.

    Sunset, Day & Moonlight Sails

    Private or small-group

  • Happy couple in love aboard Selina II.

    Perfect for couples, families & special occasions

  • Champagne glasses offered aboard your voyage on Selina II.

    BYOB friendly

    Enjoy local North Fork wine onboard

  • The friendly former Captain Iris and two very happy sailors aboard Selina II.

    Friendly, expert crew

    Relaxed & welcoming

  • The Selina II on a beautiful voyage in Greenport.

    Convenient Departures

    Greenport Village & Shelter Island

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The Top-Rated Sailing Experience on Long Island’s East End

The fantastic Selina II on a gorgeous voyage in the afternoon.

Choose Your Sailing Adventure

Sunset Champagne Sail

Golden hour magic — perfect for romance

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Day Sailing Adventure

Family-friendly sightseeing + hands-on sailing

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Moonlight Cruise

Starlight & soft breeze — dreamy evening escape

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Special Moments on the Water

  • Flexible, expert advice when you need it. Book hourly support across a range of topics—from planning to problem-solving. This focused consultation will help clarify your goals, map out next steps, and identify opportunities for growth.

  • Item description

  • Flexible, expert advice when you need it. Book hourly support across a range of topics—from planning to problem-solving. This focused consultation will help clarify your goals, map out next steps, and identify opportunities for growth.

  • Flexible, expert advice when you need it. Book hourly support across a range of topics—from planning to problem-solving. This focused consultation will help clarify your goals, map out next steps, and identify opportunities for growth.

Private Charters & Special Events

Sail the North Fork — Close to the Hamptons

Discover the beauty of Shelter Island Sound, East End Waters, and the iconic Greenport & Shelter Island waterfront.

Perfect for:

🍷 Wine country weekends

👨‍👩‍👦 Family adventures

✨ Romantic escapes

🚗 NYC travelers looking for a getaway

Give the Gift of Sailing

A SailSelinaNY gift card is an unforgettable way to celebrate birthdays, anniversaries, engagements, or surprises “just because.”

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