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,
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,
Viking Fly Charters is a classic 2008 SeaCraft center console based in Norwalk, offering private, customizable trips for up to 3 guests.
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.
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
Step aboard Seaspray, a beautifully restored 1992 SULLIVAN Chesapeake Deck boat, now updated in 2021 to ensure an exceptional cruising experience.
Step aboard the 2025 Galeon 560 Fly and experience New York Harbor like never before.
Nick's Long Island Boat Rentals offers a fun and comfortable way to explore the waters around Lindenhurst aboard a 2008 Hurricane Sundeck 2000 Deck Boat.
Gypsy Soul Tours offers private, custom sailing charters from Stamford, Connecticut, delivering unforgettable experiences on the scenic Long Island Sound.
"We had such a wonderful afternoon on the water with Captain Jon!" — Samantha,
Discover why Oyster Bay, New York is a favorite for boaters seeking calm, scenic waters along the North Shore of Long Island. Sheltered coves and broad stretches of the Sound create ideal conditions for relaxed cruising, easy anchoring, and smooth sightseeing. With tree-lined shorelines, classic waterfront homes, and gentle breezes, it's a picturesque setting for both first-time guests and seasoned captains.
Oyster Bay boating charters offer a versatile way to experience the area. Choose a comfortable motor yacht for effortless coastal exploring, a nimble sailboat to catch the afternoon wind, or a center-console for a day of light tackle and on-the-water adventure. Families enjoy leisurely picnics on deck and swim stops in protected inlets, while couples love golden-hour cruises with sweeping views.
Wildlife watchers often spot seabirds riding the thermals and occasional marine life in the quieter backwaters. Kayaks, paddleboards, and tenders add fun at anchor, turning serene bays into your private playground. On longer outings, skippers can follow the shoreline to discover new vistas and neighboring harbors, then return to Oyster Bay's welcoming moorings before dusk.
Whether you're planning a half-day escape or a full-day charter, the combination of gentle seas, varied vessel options, and postcard-worthy scenery makes Oyster Bay boating charters a standout choice. Come aboard, set a relaxed course, and enjoy an easygoing Long Island adventure from the best seat in the house—the water.
