A Century Under Sail: The Remarkable Story of Selina II
A Century Under Sail: The Remarkable Story of Selina II
How a 1926 Greenport-built Crosby catboat survived wars, hurricanes, changing generations, and the disappearance of nearly every comparable vessel to become one of Long Island’s most extraordinary sailing experiences.
If you walk the docks of Greenport today, you’ll see plenty of beautiful boats—sleek modern yachts, fishing vessels, ferries, and seasonal cruisers. Most are measured in years or decades. Very few are measured in centuries.
Yet tied to a dock or sailing gracefully across Shelter Island Sound, visitors may spot a vessel whose story began before television, before commercial air travel, and before many Long Island roads were paved: Selina II.
Built in Greenport in 1926 at Sweets Shipyard, Selina II is a rare surviving 41-foot (44 feet overall) Crosby catboat—one of only a handful of catboats ever built over 40 feet and, by many accounts, the largest and only one of its kind still sailing today. With her wide beam and massive 1,000-square-foot gaff-rigged mainsail, she was designed for stability and family cruising rather than racing. She remains in continuous family stewardship nearly a century later, a living link to Long Island’s maritime heritage.
Sailing yacht Selina II built in Greenport NY in 1926, moored at Samuel Ainsworth Hird’s private dock in Dering Harbor, Shelter Island, New York. Selina II remains in the same family over a century later.
A Yacht Built in Greenport’s Golden Age
In 1926, Greenport was a thriving working maritime town. Shipyards lined the waterfront, and skilled craftsmen built vessels for commercial fishing and coastal trade. Samuel Ainsworth Hird, whose family had deep roots on Shelter Island, commissioned Selina II from Sweets Shipyard as a family yacht. Named in honor of a beloved family name carried across seven generations of women (tracing back to his mother, Selina Ainsworth), she was elegant yet practical—built to bring people together on the water for adventures, summer gatherings, and lifelong memories.
Photographs from her early years show timeless lines and unmistakable proportions that have endured. Visitors stepping aboard today still encounter much of the original craftsmanship that the Hird family first admired.
The Waters That Shaped Her
Though built in Greenport, Selina II’s true home has always been the protected waterways around Shelter Island—Dering Harbor (where the Hird family dock was located), Shelter Island Sound, Greenport Harbor, Gardiners Bay, Peconic Bay, and Long Island Sound. These waters became inseparable from her identity. Generations of locals grew accustomed to her distinctive silhouette gliding across the Sound. She evolved from a private family yacht into a cherished piece of local maritime heritage.
Why Most Wooden Yachts Disappear
Wooden yachts endure harsh conditions: relentless saltwater, sun damage, storms, and ever-rising maintenance costs. For every historic vessel that survives, hundreds are lost to neglect, abandonment, or the economics of restoration. Selina II’s survival is due less to luck than to the unwavering commitment of her owners. Every generation faced difficult decisions and chose preservation.
When Samuel Ainsworth Hird passed in 1962, his children confronted the choice of letting her go or committing to her care. Daughter Esther Hird Hunt and her husband Bridg Hunt took on the responsibility (alongside son Sam initially). By the early 1980s, extensive structural issues threatened her existence. Bridg and Esther’s eldest son, Bridgford Hunt—who had just completed an internship with a wooden shipwright—undertook a major hands-on restoration himself, predicting it might last another 20 years.
In 2001, the boat passed to the next generation. Bridgford had become busy operating the Shelter Island Ferry, and brother Ainsworth was raising a family elsewhere. Daughter Selina Iris Hunt Robertson (known as Captain Iris) stepped up. Facing significant maintenance costs and the boat’s condition, she made a pragmatic yet visionary decision: place Selina II into charter service to generate revenue for her ongoing care. Thus began 25 years operating as Sail Selina out of St. Michaels, Maryland, on the Chesapeake Bay, where she introduced thousands of guests to classic wooden boat sailing.
A Homecoming for the Centennial
After a quarter-century on the Chesapeake—where she participated in historic parades and became a beloved fixture—Selina II returned north in 2025/2026 to her birthplace waters around Greenport and Shelter Island, just in time for her centennial. This was no relocation but a true homecoming. She continues to sail the same East End bays and harbors where her story began, now under new operational leadership that honors the multigenerational maritime legacy (including Captain Luna Crowley, who brings her own East End seafaring heritage to the helm).
Selina II has carried tens of thousands of guests over more than a century of sails, weathering not only the elements but the passage of time and shifting family circumstances. Her endurance is a testament to the Hird family’s dedication across four (and now extending into further) generations, the skill of Greenport’s shipwrights, and the enduring appeal of classic wooden boats.
Today, as she marks 100 years, Selina II stands as one of Long Island’s most extraordinary sailing experiences—a rare, actively sailed piece of American maritime history that continues to connect people to the water, just as Samuel Ainsworth Hird intended nearly a century ago.
Selina II’s story is still being written on the same winds and tides that first filled her sails. Whether you’re a history buff, a sailing enthusiast, or simply seeking a memorable day on the water, her return home offers a chance to experience a living legend in her native waters.
