Selina II – A Historic 1926 Wooden Sailing Yacht
Selina II’s Transition from St. Michaels to Long Island
Sail Selina II is a 1926 classic wooden sailing yacht with nearly a century of continuous family stewardship. From 2001 through 2025, she sailed from St. Michaels, Maryland, becoming one of the Chesapeake Bay’s most recognized historic sailing vessels. During those 25 seasons, Selina II welcomed tens of thousands of guests aboard for small-group six-guest sailing experiences (link to your main sailing tours page), combining traditional seamanship, maritime storytelling, and a calm, unhurried experience on the water. Her time in Maryland was widely covered by regional and national publications for both her preservation and her role in keeping working maritime history alive.
In 2026, Selina II returned north to Long Island’s East End, beginning a new chapter sailing from Greenport Village and Shelter Island (link to your location/departures page) on the waters of Peconic Bay and Shelter Island Sound. This relocation reflects a homecoming to the region where many classic wooden yachts were built and maintained, and where sailing remains deeply rooted in local culture. Today, Sail Selina NY continues the same intimate six-guest experience that defined her Chesapeake years, now paired with Long Island’s coastal scenery and shipbuilding heritage. The transition honors Selina II’s past while positioning her as a living historic vessel actively sailing into her second century.
In Brief
Sail Selina II is a 1926 historic wooden sailing yacht that sailed from St. Michaels, Maryland for 25 years before relocating to Greenport and Shelter Island, New York in 2026, where she now offers intimate six-guest sailing experiences on Long Island’s East End.
Maryland to New York Transition FAQs
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After completing 25 seasons sailing from St. Michaels, Maryland, Selina II relocated to Long Island to begin a new chapter aligned with her long-term preservation and sailing future. The move allows the historic yacht to continue operating as an actively sailed vessel while connecting with Long Island’s strong maritime traditions. Today, Selina II sails under the stewardship of Sail Selina NY, the business responsible for her current operations.
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Yes. Selina II is the same 1926 wooden sailing yacht, not a replica or replacement. While the operating business has changed, the vessel itself remains unchanged. Her relocation represents a geographic transition, not a change in the boat’s identity or history.
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Yes. Selina II continues to offer intimate sailing experiences limited to six guests, emphasizing calm sailing, classic seamanship, and time on the water rather than crowds or entertainment-driven tours. This continuity is intentional and reflects the values carried forward by Sail Selina NY.
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Selina II now sails from Greenport Village and Shelter Island on Long Island’s East End, primarily on Peconic Bay and Shelter Island Sound.
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Yes. Selina II is a historic wooden sailing yacht built in 1926 and remains actively sailed rather than preserved as a dockside exhibit. Under Sail Selina NY, she continues operating as a living piece of maritime history rather than a static museum vessel.
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Sailing Tradition on Long Island’s East End - Sail Selina NY
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
Sail Selina NY 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 its Semiquincentennial in 2026, Sail Selina NY stands ready to honor that milestone, just as she did 50 years ago.