Hero banner

Oyster Bay Boat Tours

The best out of 33 boat tours in Oyster Bay - enter dates to check availability

Oyster Bay Boat Tours

Trip date
banner
Loading...
Loading...

Top Boat Tours in Oyster Bay

Oyster Bay: 33 boats available

Showing 1 - 10
 Show on map
Loading...
Listing image
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
Listing image
31 ft
Up to 6 people
Carolann P Fishing Charters
5.0
/5
(2 reviews)
15 external reviews
Freeport (34 min drive 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.

"  Ray our Captain, great guy! very informative of the surrounding area we were in." —⁠ Luis,
+1
trips from
US $500
Listing image
20 ft
Up to 3 people
Viking Fly Charters
5.0
/5
(11 external reviews)
Norwalk (1 hr 16 min drive 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
Listing image
25 ft
Up to 6 people
Cast Net Charters
5.0
/5
(24 external reviews)
Island Park (46 min drive 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
Listing image
30 ft
Up to 10 people
GO With The Flo Charters
5.0
/5
(2 reviews)
Wantagh (29 min drive 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.

"We had a great time thanks to Captain Richard. He step up 2 floating stuff that was nice a sturdy." —⁠ Shaniqua, NY
+3
trips from
US $800
Listing image
56 ft
Up to 13 people
Osca Yachting
Port Washington (29 min drive from Oyster Bay)
Step aboard the 2025 Galeon 560 Fly and experience New York Harbor like never before.
+1
trips from
US $3,750
Listing image
51 ft
Up to 30 people
Seaspray
4.8
/5
(2 reviews)
31 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
Listing image
44 ft
Up to 6 people
North River Sailing – Tantara
5.0
/5
(1 review)
New York City (13.3 miles from Oyster Bay)
We’re setting sail across Long Island Sound this season from our home base on historic City Island.
trips from
US $600
Listing image
37 ft
Up to 6 people
Gypsy Soul Tours
5.0
/5
(3 reviews)
Stamford (1 hr 8 min drive from Oyster Bay)
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,
+2
trips from
US $750
Listing image
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

According to customer reviews, some of the most popular boat tours in Oyster Bay, New York are:
Full list of top boat tours in Oyster Bay
According to customer reviews, some of the most popular boat tours in Oyster Bay, New York are:
Full list of top boat tours in Oyster Bay
The average Oyster Bay boat trip price for a 4 hour private trip is US $636 based on prices on BoatBooker.com.
The average Oyster Bay boat trip price for a 4 hour private trip is US $636 based on prices on BoatBooker.com.
The top 5 most popular boat types you can rent in Oyster Bay, by number of boats available are:
The top 5 most popular boat types you can rent in Oyster Bay, by number of boats available are:
The top 5 most popular boat categories you can rent in Oyster Bay, by number of boats available are:
The top 5 most popular boat categories you can rent in Oyster Bay, by number of boats available are:
According to customer reviews on BoatBooker.com, some of the best rated boat tours in Oyster Bay are:
According to customer reviews on BoatBooker.com, some of the best rated boat tours in Oyster Bay are:
The average price of boat tours in Oyster Bay is:
  • 2-hour boating trips – US $525
  • 3-hour boating trips – US $675
  • 4-hour boating trips – US $800
  • 8-hour boating trips – US $1,475
The average price of boat tours in Oyster Bay is:
  • 2-hour boating trips – US $525
  • 3-hour boating trips – US $675
  • 4-hour boating trips – US $800
  • 8-hour boating trips – US $1,475
Powered by AI

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.

How people rated boat trips in Oyster Bay

  • Windward Sailing Charters
    Windward Sailing Charters
    Boat rentals in Oyster Bay
    5.0
    /5
    (4 Hour Sunset Charter)

    Great Evening on the Water

    From the start, Jonathan was both a gracious host and a skilled, knowledgeable captain. His communication with us both before and during our 4-hour sunset cruise was casual, welcoming and thorough- and helped us enjoy every step along the way. "Windswept" was comfortable, capable and beautifully maintained- making for a relaxing, yet engaging sailing experience. Highly recommend!
    Todd R.
    Todd R.
    Reviewed on Jun 24, 2026
  • Windward Sailing Charters
    Windward Sailing Charters
    Boat rentals in Oyster Bay
    5.0
    /5
    (3 Hour Private Sailing Charter)

    Amazing!

    Jonathon welcomed my friends & I aboard as if we were family! He went above & beyond to make us comfortable in his space. He was very knowledgeable in sailing as my husband loves to learn & chat about it all. The boat was the perfect size for the 5 of us with plenty of room. The bathroom was so large for a sail boat! Getting to the sailboat was so easy & quick. We will definitely be looking to book with Jonathon again.
    Amanda J.
    Amanda J.
    Reviewed on Aug 3, 2025