Real Good People: Shannon Carleton
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At The Helm In The Hamptons With Shannon Carleton

Gliding effortlessly across Sag Harbor Bay, the schooner Kelpie is perhaps one of the most breathtaking sights in all of the Hamptons. Her 78-foot profile and towering sails are straight out of a movie, and coming aboard feels like a step back in time. A traditional gaff-rigged schooner, Kelpie was designed and built at the Harvey Gamage Shipyard in Maine in 1928. Her esteemed history includes hunting German U-boats in WWII, hosting A-listers like Paul Newman and Elizabeth Taylor as charter guests, and racing in—and winning—more regattas than her trophy cabinet can hold.

Today, Kelpie’s old world charm and storied past are preserved and celebrated through her current role as a luxury sailing charter throughout the gorgeous harbors and hidden coves of New York’s North Fork. Everything aboard Kelpie drips with decadence—champagne in sparkling crystal flutes, Scottish wool blankets, sumptuous cheese boards and delicious local bites, all served on platters by white-gloved crew members in matching outfits. Simply put, it is pure perfection. And at the helm is our friend and captain, Shannon Carleton.

Growing up on and around boats, Shannon always had a love for the ocean. As a kid, she spent her summers on Fire Island, rebuilding her family’s motor yacht with her dad. In 2001, she learned the art of traditional sailing on a gaff-rigged schooner during a semester at sea with Ocean Classroom, sailing 1,900 miles from Dominica to Greenport, NY. The experience was one giant light-bulb moment.

“That semester shaped my entire life,” Shannon tells us. “I was 20 years old, and I had no sailing experience. But every moment of that semester, I knew I wanted to be a schooner captain.”

Years later, with her dreams solidified and a plan intact, all Shannon needed to do was land a boat. And when she found Kelpie for sale in Barcelona, it was a match made in heaven. “I had admired boats like Kelpie for years, though I never thought owning one would happen,” Shannon recalls. “I found her in Spain, so getting her stateside was an adventure in its own right. I could have found something in the U.S., but she was the dream. She was what I wanted my entire life.”

Before shipping Kelpie to her new home in the States, Shannon spent two months in Europe sailing around the Mediterranean. Topping her list of pinch-me sailing moments is the Italian coastline.

“It was like something out of a magazine or a movie—a vintage classic yacht right off the coast of Italy, and I’m just sitting on Kelpie staring at all the beautiful buildings. That was a very, very magical experience.”

Once back stateside, Shannon set up her charter operation in Montauk, before moving to Sag Harbor in 2011. From the moment she anchored up in Sag, she fell in love with the quaint little village. “You don't need a car. You can pull your dinghy up anywhere and walk. It’s a very close-knit community. I just love this town.”

Shannon and her crew all live aboard boats full-time in Sag Harbor (Shannon on Kelpie and her crew on neighboring vessels). So each day, the first order of business is to collect the crew, bring them to Kelpie and begin the laundry list of tasks in preparation for the day’s charter. A funny coincidence, Kelpie’s launch boat, Siren, was a vineyard vines-branded launch in Newport, RI, called The Pink Whale II. Even though Shannon changed the name (she prefers mythical sea creature names like Kelpie, a shape-shifting horse of Scottish lore) she kept the smiling whale life ring for good luck.

Kelpie is a racing schooner—a distance racing record holder, she was long referred to as “the fastest schooner on the West Coast”—so ensuring smooth sailing during a charter is one of the hardest parts of the whole operation.

“I don't have a lot of room for error, especially in these very narrow channels, so keeping her reigned in is very difficult,” Shannon explains. “Other sailors will say, ‘Why did you buy a thoroughbred to give pony rides?’ Well, that's not why people charter Kelpie. I don't want all the crystal serving ware to go flying. One day I'll race her, but right now I just love what I'm doing.”

Whether she’s dismissing comments about her sailing technique or having to work extra hard to establish her business, Shannon has certainly encountered her fair share of setbacks as a woman working in a predominantly male industry. “There’s some criticism from gents in the industry, but I can’t really say it bothers me. The benefit to being a woman at the helm is that even while paying attention to wind, water depth, tide/current and sail trim, I can spot things most men wouldn’t—the wrong spoon in the caviar or a glass of wine lacking condensation, signaling me to radio my stewardess to pop an ice cube into a guest’s rosé. Those instincts come from being a lady who likes to entertain, and that’s not a common trait among sea captains.”

Living and working on her boat doesn’t leave much time for adventures on land. But when Shannon does come ashore, she makes sure to stop at her favorite place in all of Sag Harbor, the American Hotel, where attention to detail is an artform. Located on historic Main Street in the heart of downtown, the hotel dates back to 1846 and exudes an old world vibe similar to that of Kelpie. “It’s my absolute favorite spot,” Shannon gushes. “I will find excuses just to go in there. Sometimes I’ll grab a coffee before I have to be somewhere, and they set up a table beautifully. They bring my dog Andy her little dish of water. They're very, very accommodating. And they have that same vintage feel that Kelpie has. It’s like you're going back in time.”

Whether it’s a quick errand or a full day in town, Shannon always makes a point to head back to Kelpie for golden hour. “My favorite time of day aboard Kelpie is before sunset, when I'm finished with whatever the day was about. I pour a glass of rosé, sit on deck in those cute little teak chairs with my dog Andy. The way the sun hits the varnish, it's golden hour amplified—and I just look at this boat and say, ‘Wow, this is everything that I've ever wanted.’ I love what I do, and I'm reminded of that almost every day.”

We’ll cheers to that, Shannon.

To learn more about Shannon and her crew and to book a charter, visit

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