We’re setting sail across Long Island Sound this season from our home base on historic City Island. With its network of islands, lighthouses, sheltered harbors, and classic coastal towns, this area offers one of the most scenic and rewarding sailing experiences near New York City.

Every trip is fully bespoke and designed around your ideal day on the water. Whether you want a relaxed sailing cruise, a swim stop in calm waters, hands-on sailing instruction, or a more advanced heavy-weather sailing experience, the experience is tailored entirely to you. We also offer longer coastal passages and one-way adventures, giving you the chance to truly travel by sail toward destinations like the Hamptons, Long Island’s North Shore, or the Connecticut coastline.

City Island itself is part of the journey, a charming maritime community in The Bronx with a rich boatbuilding heritage and a relaxed coastal atmosphere that feels far removed from the city, yet is easily accessible by public transportation.

We offer private day sails, sailing lessons, coastal passages, sunset sails depending on timing, and special occasion trips such as proposals, engagements, anniversaries, and celebrations, all with a focus on creating memorable and personalized moments on the water.

Our boat, Tantara, was designed by the legendary Sparkman & Stephens and built at Minneford Yacht Yard on City Island, a collaboration deeply rooted in New York’s maritime history. She is a 44-foot ocean-racing yacht built for offshore performance, safety, and stability, while also offering a spacious and comfortable deck ideal for relaxing, enjoying the skyline, or spending a full day at sea.

Your captain, Sam, has been sailing since the age of 12, starting on Lake Michigan in Chicago and continuing his journey through Maine before settling in New York City over a decade ago, bringing extensive experience and a strong focus on safe, enjoyable, and personalized sailing for all levels.