Historic Sailing Charters in Greenport & Shelter Island, NY

Private sails aboard Selina II — a 1926 Crosby catboat built in Greenport and sailed by the same family for four generations. Limited to six guests by design.

Book Now
Sailing Trips

A Different Kind of Long Island Sailing Charter

Sail Selina NY offers private sailing charters aboard Selina II, one of the largest surviving vintage Crosby catboats in the world. Built at Sweets Shipyard in Greenport, New York in 1926, Selina II has carried more than 60,000 guests across Peconic Bay and Long Island Sound over more than 11,000 sails.

Captain Luna Crowley, great-granddaughter of legendary East End captain Frank Mundus, continues a multigenerational maritime legacy aboard this living piece of history. Every voyage is limited to six guests — not as a restriction, but as a commitment to the kind of unhurried, intimate experience these waters deserve.

In 2026, Selina II marks 100 years afloat — returning home to Greenport and Shelter Island for her centennial season

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

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.

  • Say “I do” aboard our 1926 vintage catboat in the Hamptons. Perfect for intimate weddings, elopements, and vow renewals, Sail Selina NY offers a timeless, romantic backdrop on the water. Celebrate with elegance, charm, and unforgettable views.

  • 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

Private Sailing Charters in Greenport & Shelter Island, NY

Sail Selina NY offers private sailing charters aboard Selina II, a 1926 Crosby catboat built in Greenport and sailed by the same family for a century. Every charter is completely private — no shared trips, no strangers — and limited to six guests by design.

What Makes Sailing on Selina II Different?

  • A genuinely historic vessel — Selina II is a 1926 Crosby catboat, one of the largest surviving vintage catboats in the world, built at Sweets Shipyard in Greenport, NY

  • Completely private — your group only, never mixed with other guests; maximum six people aboard

  • Multigenerational maritime legacy — captained by Luna Crowley, great-granddaughter of legendary East End captain Frank Mundus

  • Sailing from two iconic East End locations — Greenport, NY and Dering Harbor, Shelter Island

  • Calm, scenic waters — Peconic Bay and Shelter Island Sound, away from crowded tourist boat routes

  • Flexible occasions — proposals, anniversaries, sunset sails, corporate outings, wine tastings with Peconic Bay Winery

Who This Sailing Charter Is For

  • Couples seeking a romantic, private sailing experience on Long Island's East End — proposals and anniversaries especially welcome

  • Visitors to Greenport or Shelter Island who want something genuinely memorable, not a standard harbor tour

  • Small groups of up to 6 — families, friends, or colleagues looking for an intimate private charter on Peconic Bay

  • The Chequit hotel guests — priority booking available for guests staying at The Chequit on Shelter Island

  • History and craftsmanship enthusiasts drawn to authentic, living maritime heritage

What to Expect on Your Sail

A private sailing voyage of 2–3 hours aboard a 100-year-old wooden catboat, with a licensed captain at the helm. Selina II moves quietly under sail — no engine noise, no crowds, no itinerary pressure. Guests are welcome to bring their own food and drinks. The experience is unhurried by design: Peconic Bay and Shelter Island Sound reward the patient sailor. Captain Luna Crowley handles everything on deck. Your only job is to be present on the water.

A Different Kind of Sailing Experience on Long Island

Selina II is not a party cruise, a harbor shuttle, or a replica tall ship. She is a rare, actively sailed piece of American maritime history — carrying guests across the same waters she has sailed since 1926. Over 11,000 sails. More than 60,000 guests. The same family, the same boat, the same waters. If you're looking for the best sailing charter on Long Island's East End, this is it — not because it's the loudest, but because it's the only one of its kind.

Frequently Asked Questions

  • Sail Selina NY offers private sailing charters aboard Selina II, a 1926 Crosby catboat sailing from Greenport and Shelter Island, New York. Captained by Luna Crowley, voyages are limited to six guests for an intimate, historic sailing experience on Peconic Bay.

  • Charters depart from Greenport, NY and Shelter Island, NY (including Dering Harbor). Sail Selina NY is also docked minutes walk from The Chequit hotel on Shelter Island during the 2026 season, offering priority access for hotel guests.

  • All charters are limited to six guests maximum. This is intentional — Selina II is a rare, century-old wooden vessel, and keeping groups small ensures each guest has a genuinely personal experience.

  • Sail Selina NY offers day sails, sunset sails, private event charters (proposals, anniversaries, micro weddings), bachelorette sails, wine tasting sails with Peconic Bay Winery and Krissie Vineyards, and sailing instruction.

  • You can book directly at sailselinany.com. Early season advance booking discounts are available. Contact Captain Luna Crowley at 631-500-0763 or sailselinany@gmail.com with any questions.

Give the Gift of Sailing

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

BUY GIFT CARDS