The classic 78-foot gaff-rigged schooner, originally built in Maine in 1928 and once used by the U.S. Coast Guard during World War II, has quietly become one of the most recognizable fixtures in the harbor. But unlike so much of modern Hamptons luxury culture, Kelpie’s appeal has very little to do with spectacle. The yacht feels deeply personal — less a business than a floating extension of Shannon herself.

Tall, blonde, effortlessly pretty in that distinctly maritime American way, she somehow always appears exactly as one imagines the owner of a beautifully restored sailing yacht should: windswept hair, white linen, oversized sunglasses, barefoot on teak, moving through the harbor as though she were born to it. The entire atmosphere — the polished wood, the cream upholstery, the soft lighting, the silver trays of Cavaniola’s, the quiet confidence of it all — feels remarkably cohesive. Ralph Lauren campaign energy, if Ralph Lauren had spent more time offshore in Sag Harbor.

And yet what separates Shannon from the endless procession of carefully curated Hamptons personalities is that she never seems overly polished. Her Instagram lingers not only on idyllic lunches and impossibly elegant golden-hour sails, but also on the far less glamorous reality of preserving an old yacht: sanding, repairs, hauling equipment, winter breakdowns, maintenance, weather, exhaustion. One moment she is serving chilled rosé and local cheeses on deck beneath cream-colored blankets; the next she is filming herself navigating through rough squalls while the rest of the Hamptons retreats indoors beneath cedar roofs and dinner reservations.

That contrast may be precisely why people are so drawn to her.

Because Kelpie is not fantasy in the influencer sense. It is a real boat, with real labor behind it, navigated by someone who genuinely understands and loves life at sea. The elegance comes not from perfection, but from stewardship.

To spend an afternoon aboard Kelpie is apparently to forget, briefly, the louder version of the Hamptons entirely. Guests are tendered from shore into a world of polished brass, salt air, candlelight, and slow conversation — part boutique hotel, part private home, part old-world sailing culture. Kelpie offers private sails ranging from sunset charters to half- and full-day experiences for up to 24 guests.

And while Shannon rarely leads with pricing — which somehow only adds to the mystique — comparable classic schooner experiences in Sag Harbor often begin around $3,900–$5,500 for shorter sails and rise significantly for longer bespoke charters and peak summer weekends. Kelpie itself provides rates privately upon inquiry, which feels entirely appropriate for something that operates more like a discreet floating salon than a traditional charter business.

In a place where luxury is so often performed, Shannon Carleton has managed to create something that feels unusually authentic.

Which may explain why Kelpie has become less of a yacht and more of a harbor institution.

for rates, information, and bookings, visit yachtkelpie.com