Windward Sailing Charters
Sail Long Island's Gold Coast aboard a beautifully maintained 2012 Jeanneau Sun Odyssey 36i.
"From the start, Jonathan was both a gracious host and a skilled, knowledgeable captain." — Todd,
Sail Long Island's Gold Coast aboard a beautifully maintained 2012 Jeanneau Sun Odyssey 36i.
"From the start, Jonathan was both a gracious host and a skilled, knowledgeable captain." — Todd,
Experience timeless elegance and adventure aboard Montauk Venture Charters, a beautifully restored 1961 Hatteras Sportfish Motor Yacht, fully refreshed in 2020.
Carolann P Fishing Charters is a beautifully restored 1998 Luhrs 31 Sportfishing vessel (restored in 2025), based in Freeport, offering an unforgettable maritime experience for up to six guests.
" Ray our Captain, great guy! very informative of the surrounding area we were in." — Luis,
Step aboard “GO FISH”, a 1987 Pursuit 2550 Center Console Cuddy Cabin operated by Cast Net Charters and based out of Island Park—perfect for unforgettable days on the water for up to 6 guests.
Experience Montauk from the water with a Grady-White 30 and enjoy a private charter designed entirely around your group.
Experience luxury and adventure with Ocean Breeze Yacht Rental LLC aboard this stunning 2006 Meridian 411 Sedan Bridge, based in New York City.
"Honestly what an easy and enjoyable experience for everyone!" — Kristen,
Step aboard Seaspray, a beautifully restored 1992 SULLIVAN Chesapeake Deck boat, now updated in 2021 to ensure an exceptional cruising experience.
Set sail with VitaminSea Voyages, a premium boating experience departing from the scenic shores of Montauk aboard a 2011 Steiger Craft Miami Cuddy Cabin.
"Bachelor party sunset cruise was excellent! The captain and crew made us feel safe and really took care of us." — Carlos,
GO With The Flo Charters is a beautifully restored 2001 Pursuit 3070 Offshore Center Console (refit in 2026), delivering the perfect mix of performance, comfort, and reliability.
"Been going out with Capt Rich for years and ALWAYS have the best time." — Luie, New York
See New York from the water and discover why this storied destination belongs on every boater's list. New York boating charters unlock sweeping views of the skyline as you cruise the Hudson River, the East River, and New York Harbor—prime vantage points for landmarks and photo‑worthy cityscapes.
From leisurely harbor loops to longer skyline circuits, charters commonly trace routes past the Statue of Liberty, Ellis Island, Governors Island, and under the Brooklyn and Manhattan Bridges. Smooth currents and wide channels make sightseeing simple, while experienced captains can highlight history, architecture, and neighborhood shorelines from Lower Manhattan to the Upper West Side.
New York boating charters are ideal for daytime city tours with crisp, unobstructed views, sunset voyages that set the skyscrapers aglow, and evening cruises showcasing twinkling lights along the waterfront. Seasonal outings bring their own magic—fresh spring breezes, warm summer afternoons on deck, and vibrant fall foliage upriver.
Whether you're planning a private celebration, a small‑group excursion, or a relaxed afternoon on the harbor, the city's interconnected waterways offer flexible itineraries, calm anchorages in designated areas, and countless backdrops for memorable photos. Choose a vessel and route that fit your style, and experience New York's energy from its most iconic stage—the water.


