Classic Sailing Charters on Long Island’s East End

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

Book Now
Sailing Trips

Limited to six guests for the most intimate experience

Celebrating 100 Years

●

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 Selina NY?

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

    Built in Greenport in 1926

    Authentic maritime heritage

  • Beautiful sunset photo of Sail Selina NY. 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. Sail Selina NY

    Perfect for couples, families & special occasions

  • Champagne glasses offered aboard your voyage on Sail Selina NY.

    BYOB friendly

    Enjoy local North Fork wine onboard

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

    Friendly, expert crew

    Relaxed & welcoming

  • Sail Selina NY on a beautiful voyage in Greenport.

    Convenient Departures

    Greenport Village & Shelter Island

Explore Sailing Trips

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

  • Five green circles indicating a five-star rating for a review titled 'Beautiful Night on the Water' about a boat trip on a lake, written by a reviewer in Nazareth, Pennsylvania, in July 2023.
  • Five green circles indicating a five-star rating.
  • Tripadvisor review page for El Calafate, Argentina, titled 'Educational and spiritual experience' by JoAnn B, posted September 2023, with a 4 out of 5 rating.
  • A Tripadvisor review with a five green dot rating, dated May 31, 2024, expressing a positive experience on a sailing excursion with Iris and Colin, mentioning they were wonderful and enjoyable companions.
  • Tripadvisor review celebrating a 7th wedding anniversary aboard Sail Selina II with a green five-dot icon and text about sailing experiences, views of the Miles River, and historical connections to the Delmarva Peninsula.
  • A travel review featuring a boat in Etters, Pennsylvania, with a green star rating.
  • Photos of a boat and sailboats on a body of water during sunset in a scenic harbor.
  • Colorful waterfront houses reflected in the water.
  • Three photographs of people enjoying a sailing cruise on Chesapeake Bay, including a man in a white shirt and straw hat, and a view of a sailboat's mast and sail against the sky.

Choose Your Sailing Adventure

Sunset Champagne Sail

Golden hour magic — perfect for romance

View Sunset Sails

Day Sailing Adventure

Family-friendly sightseeing & hands-on sailing

View Day Sails

Moonlight Cruise

Starlight & soft breeze — dreamy evening escape

View Moonlight Cruises
All Sailing Trips

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

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

Sail the North Fork — Close to the Hamptons

Give the Gift of Sailing

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

BUY GIFT CARDS