About Us
Meet Your Captain - A Local Greenport Sailor with Deep Maritime Roots
At the helm today is Capt. Luna Crowley, a lifelong East End mariner. Raised in and around Greenport, Luna earned her captain’s license in her early twenties. Maritime heritage runs deep in her family: her great-grandfather was Capt. Frank Mundus, the legendary shark fisherman who inspired the character in Jaws, and her aunt Pat Mundus ran a charter boat out of Greenport.
Together with her crew, Capt. Luna blends professional seamanship with warm hospitality. Guests consistently praise the team’s storytelling, attentiveness, and ability to make every sail feel personal and unforgettable.
Grew up around Greenport, earned captain’s license in her early 20s
Multi-generational Maritime heritage: great-grandfather Capt. Frank Mundus (of Jaws fame), aunt Capt. Pat Mundus (Greenport charter captain).
Best in Luxury, Best in Boat Tours, Best in Service
Celebrating 100 Years
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Celebrating 100 Years ✳︎
To be Greenport, NY’s & Shelter Island, NY’s #1 attraction. Why do we do that? Because people like you, our passengers, look for sailboat trips that are unique, upscale, and exclusive. Our goal is to have you highly recommend us to all your friends.
Experience the luxury of sailing aboard SailSelinaNY, where we limit our guests to just 6 guests, ensuring an intimate and personalized journey through the rich history of sailing. Say goodbye to crowded boats with over 20 passengers, where you often feel like just another face in the crowd. During your 2-hour cruise, you and our fellow guests enjoy dedicated, attentive service, ensuring every detail is tailored to your personal preferences and creating an unforgettable experience.
Whether you're joining a public boat tour or booking a private charter, each Greenport, New York sailing charter includes a one-on-one, personalized tour with our knowledgeable, first-class captains and friendly crew. We make it easy for you to book your boat cruise online, so you can start your adventure with just a few clicks.
Sailing Tradition on Long Island’s East End - SailSelinaNY
Built in 1926 at Sweets Shipyard in Greenport
Largest surviving catboat ever built
41’ length on deck, 44’ overall, 1,000 sq. ft.
gaff-rigged mainsail
Famous for sailing in Operation Sail 1976 Bicentennial Parade of Tall Ships in NYC
Restored multiple times to preserve her legacy
SailSelinaNY is no ordinary boat. She is Selina II, the largest surviving catboat ever built. Crafted in 1926 at Sweets Shipyard in Greenport, she was commissioned by Samuel Ainsworth Hird, who served as her master until his passing in 1962. From then until 2001, Selina II was lovingly stewarded by his daughter and son‑in‑law, who undertook a major rebuild in the 1980s to preserve her legacy.
When she passed into new hands in the early 2000s, Selina II was in dire condition. A painstaking restoration brought her back to life, ensuring that her gleaming mahogany, brass fittings, and 1,000‑square‑foot gaff‑rigged mainsail continue to inspire awe. Measuring 41 feet on deck and 44 feet overall, she remains a living piece of maritime history.
Her greatest claim to fame came in 1976, when she sailed proudly in Operation Sail, the Bicentennial Parade of Tall Ships in New York Harbor. As America approaches itsSemiquincentennial in 2026, SailSelinaNY stands ready to honor that milestone, just as she did 50 years ago.
Our Legacy: 100 Years of Family Stewardship & Maritime Tradition
Four generations of stewardship: Samuel Ainsworth Hird (1926–1962), family caretakers (1962–2001), major rebuild in the 1980s, restoration in the 2000s
Still family-owned, still sailing strong 100 years later
Preparing to honor America’s Semiquincentennial in 2026
For nearly a century, Selina II has been part of one family’s story — and now she becomes part of yours. Four generations have cared for her, ensuring that every guest who steps aboard experiences not just a sail, but a connection to history.
Why SailSelinaNY Offers the Best Private Sailing on Long Island’s East End
Historic authenticity – Step aboard a yacht that has sailed for 100 years.
Exclusive intimacy – Just six guests per sail, ensuring privacy and comfort.
Living history – Hear stories of Greenport’s shipbuilding past and Selina II’s role in America’s maritime celebrations.
Romance & adventure – From proposals to family outings, every sail is tailored to your story.
Hospitality & Expertise
Warm, professional crew
Storytelling that brings maritime history alive
Personalized experiences for couples, families, and groups
A Sailing Experience That Feels Personal, Meaningful & Timeless
SailSelinaNY is more than a charter — it’s a chance to slow down, reconnect, and experience Long Island’s East End as it was meant to be: by water, under sail, with history at your fingertips.
Sailing From Greenport & Shelter Island — Close to the Hamptons
Whether you’re exploring the North Fork for the weekend, touring Long Island wine country, or taking a quick ferry ride from Sag Harbor or the Hamptons, SailSelinaNY is your closest and most intimate classic sailing experience.