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Hamptons & Bahamas Luxury Sailing Charters

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Person and dog on a yacht named Leaf Chaser with a clear blue sky in the background. The person is adjusting equipment, and the dog is standing on the yacht's deck.

Woman wearing large sunglasses, a blue cap, and a striped top, taking a selfie on a boat with a body of water and boats in the background on a sunny day.

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A grill with flames cooking meat on a boat, with a lake and mountains at sunset in the background.

A sailboat docked at a marina with a mountain and other boats in the background under a partly cloudy sky.

Two people standing in shallow clear water at a beach, with large rocks and sailboats in the background under a blue sky.

A woman wearing sunglasses and a red and white striped shirt lying on a black surface, with a curly-haired dog resting nearby.

A smiling couple taking a selfie on a boat with a scenic ocean view and islands in the background.

Group of six people and three dogs on a boat, enjoying a sunny day on the water with blue sky and sailboats in the background.

Sunset over a calm ocean with a sandy beach in the foreground, a large piece of driftwood on the sand, and rocks along the shoreline.

A round metal tray of oysters on ice with lemon slices, hot sauce, and cocktail sauce, surrounded by empty glasses on a wooden table. Two people are eating oysters.

Cooked steak on a wooden cutting board, sliced to show a pink center, with a grilled bone-in ribeye or T-bone steak next to it.

Man sitting in a small boat on the water, holding the motor's handle, with a marina and cloudy sky in the background.

A man in a captain's hat, glasses, and patterned shorts sitting shirtless on a boat, holding a glass, with the ocean and sky in the background.

Two dogs and two people on a sailboat enjoying drinks and each other's company during sunset.

Two women and two dogs on paddleboards floating on a lake with green hills and a partly cloudy sky in the background.

Bachelorette party sitting around a wooden dining table with snacks, drinks, and a tablet. One person is opening a bottle of wine, while others are seated or standing nearby. The setting appears to be a casual indoor gathering.

Two white plates with assorted cheeses, grapes, olives, and cured meats for bachelorette party on a sailboat in Hamptons new york

Montauk lighthouse on a grassy hill under a clear blue sky, with tall grasses in the foreground.

A young man with sunglasses relaxing on a boat near sag harbor and montauk and islands in the background under a partly cloudy sky.

A man wearing a large sun hat and a gray hoodie paddling a blue paddleboard in the ocean, with a yellow life jacket on a curly-haired dog also on the paddleboard. A sailboat is in the background, and the sky is partly cloudy with a landmass visible i

A smiling woman and a smiling man each holding a small, curly-haired dog, standing on a boat with the ocean and a sunset in the background.

Calm ocean at sunset with a colorful sky and scattered clouds

Serene sunset over a calm body of water with a treeline silhouette on the horizon and a sky with orange, yellow, and blue hues.

Two adorable curly-haired dogs with black noses and dark eyes standing closely on a boat deck during sunset.

A sailboat floating on calm Hamptons New York water during sunset with a partly cloudy sky.

A woman from a bachelorette party sits on the deck of a boat with arms outstretched, smiling, at sunset over the ocean. She is barefoot, wearing shorts and a dark jacket, with two large white buoys on either side of her.

Person wakeboarding behind a boat on a water body under a partly cloudy sky.

A collection of various seashells of different shapes, sizes, and colors, arranged on a white surface.

Two curly-haired dogs sit by the water with a sailboat in the background during dusk.

Woman swimming with a curly-haired dog in clear turquoise ocean water, with a cloudy sky in the background.

Curly-haired dog with its tongue out standing on a sandy beach near the shoreline with ocean and cloudy sky in the background.

Sailing boat on open water during sunset with colorful sky and calm waves.

Ocean view at sunset with pink and purple clouds in the sky, part of a boat's stern in the foreground.

A man wearing white clothing, sunglasses, and a wide-brimmed hat sitting at the helm of a sailboat on a sunny day, with a view of the ocean and another boat in the background.

About Elysian Sailing

Josh Gillespie is a retired U.S. Naval officer serving 12 years active duty as a ship navigator, steam engineering officer, and senior watchstander piloting the world’s busiest ports across Asia. After a decade on Wall Street, he returned to his lifelong sailing passion in 2023 — and bringing his love for the water to others on his Lagoon 450 catamaran. He currently holds a US Coast Guard 200 ton captains license

Pip, 1st mate, can be hired for ear scratches and dog treats, but is an unreliable watchstander. Super friendly to all dogs and humans.

Summer Escapades

53 Bay St, Sag Harbor
New York, NY 11963

Custom pick up / drop off locations available throughout the Hamptons

Winter Escapes

Nassau and throughout the Exumas, Bahamas

Contact

info@elysiansailing.com
(631) 833-6566

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