Oyster Bay Boat Tours

The best out of 31 boat tours in Oyster Bay - enter dates to check availability

Oyster Bay Boat Tours

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Top Boat Tours in Oyster Bay

Oyster Bay: 31 boats available

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36 ft
Up to 6 people
Windward Sailing Charters
5.0
/5
(3 reviews)
Oyster Bay
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,
+5
trips from
US $525
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50 ft
Up to 13 people
Long Island Yacht Rentals – Tranquility
5.0
/5
(1 review)
Oyster Bay
Yacht rental includes watersports. Step aboard Long Island Yacht Rentals, a luxurious 2001 Carver 466 Motor Yacht, beautifully restored in 2025 and based in scenic Oyster Bay.

"Captain Jeff was great, the boat was great, the water activities activities were great." —⁠ Joyce,
+1
trips from
US $1,800
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31 ft
Up to 6 people
Carolann P Fishing Charters
5.0
/5
(8 external reviews)
Freeport (16.0 miles from Oyster Bay)
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.
+1
trips from
US $500
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25 ft
Up to 6 people
Cast Net Charters
New
5.0
/5
(19 external reviews)
Island Park (19.4 miles from Oyster Bay)
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.
trips from
US $500
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56 ft
Up to 13 people
Osca Yachting
New
Port Washington (9.3 miles from Oyster Bay)
Step aboard the 2025 Galeon 560 Fly and experience New York Harbor like never before.
+1
trips from
US $3,500
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37 ft
Up to 6 people
Gypsy Soul Tours
New
Stamford (11.7 miles from Oyster Bay)
Gypsy Soul Tours offers private, custom sailing charters from Stamford, Connecticut, delivering unforgettable experiences on the scenic Long Island Sound.
+2
trips from
US $750
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30 ft
Up to 10 people
GO With The Flo Charters
5.0
/5
(1 review)
Wantagh (15.1 miles from Oyster Bay)
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
+3
trips from
US $800
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20 ft
Up to 3 people
Viking Fly Charters
5.0
/5
(4 external reviews)
Norwalk (17.2 miles from Oyster Bay)
Viking Fly Charters is a classic 2008 SeaCraft center console based in Norwalk, offering private, customizable trips for up to 3 guests.
+1
trips from
US $295
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51 ft
Up to 30 people
Seaspray
4.8
/5
(2 reviews)
27 external reviews
Freeport (35 min drive from Oyster Bay)
Step aboard Seaspray, a beautifully restored 1992 SULLIVAN Chesapeake Deck boat, now updated in 2021 to ensure an exceptional cruising experience.
trips from
US $800
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40 ft
Up to 10 people
Charter Nirvana
Mamaroneck (57 min drive from Oyster Bay)
Step aboard Nirvana, a timeless 38’ Pearson 386 sailing yacht, and experience the beauty of Long Island Sound without the crowds, just you, your guests, and the open water.
+2
trips from
US $440

Frequently Asked Questions about Boat Tours in Oyster Bay

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Boating in Oyster Bay

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.

What people said about boating in Oyster Bay

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How people rated boat trips in Oyster Bay

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Nearby Boating Destinations

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