Things to Do in Oyster Bay (Western Long Island Sound)

It’s all about sailing and oysters

Explore the Western Long Island Sound - the area from New Haven, CT west to City Island and the Throgs Neck Bridge. There are plenty of things to do in Oyster Bay and the neighboring harbors on both the NY and CT side - try one of our Long Island fishing charters, or indulge yourself at one of the waterfront restaurants in Stamford or Greenwich, CT. Go for an Oyster Bay sailing leisure trip, or plan a sunset cruise in Northport Harbor past the Willie K. Vanderbilt estate.

Brewer Post Road Boat Yard

Brewer Yacht Yard at Glen Cove

Derecktor New York

Glen Cove Marina, a VMG Marina

Glen Cove Yacht Club

Glen Cove Anglers Club

Hempstead Harbour Club

Jakobson Shipyard Inc

Mamaroneck Bch Cabana & Yacht Club

McMichael Yacht Brokers

McMichael Rushmore Yard

Nichols Yacht Yard

Orienta Yacht Club

Oyster Bay Marine Center

R. G. Brewer

Roosevelt Memorial Park Marina

Sagamore Yacht Club

Seawanhaka Corinthian Yacht Club

The Waterfront Center

Total Marine LTD

Avalon on Stamford Harbor

Brewer Yacht Haven

Catalano & Sons

Cummings Park Marina

Cove Island Park Marina

Ebb Tide Marina

Grass Island Marina

Greenwich Boat & Yacht Club

Greenwich Point Park Marina

Halloween Yacht Club

Harbour Square Marina

Indian Harbor Yacht Club

Stamford Landing Marina

Old Greenwich Yacht Club

Rudys Tackle Barn

The Ponus Yacht Club

Stamford Yacht Club

Delamar Greenwich Harbor Marina

Delamar Greenwich Harbor Marina

Long Island Fishing Charters

Long-Island-Fishing-Charters1
The Western Long Island Sound is a special body of water with a range of marine life including stripers, fluke, and seabass. Cast off the lines on one of Sailo’s fishing charters and we guarantee that you’ll increase the odds for a successful fishing trip. Try one of our favorite things to do in Oyster Bay: load up your bait-wells, make sure your cooler is packed with ice, and take full advantage of the clear waters of these fertile fishing grounds.

    Suggested Boats

  • Fish on the Long Island Sound in a Sporty and Comfortable boat
    $575

    Fish on the Long Island Sound in a Sporty and Comfortable boat
    Port Chester, NY

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  • Go light tackle/fly fishing with this nice Classic Mako!
    $500

    Go light tackle/fly fishing with this nice Classic Mako!
    City Island, NY

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  • Make your next fishing trip memorable with us
    $585

    Make your next fishing trip memorable with us
    Greenwich, CT

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Waterfront Restaurants in Stamford, CT

Waterfront-Restaurants-Stamford-CT
At Sailo, we love fresh seafood. After a day out on the water on your Sailo sloop, waterfront dining in Stamford, CT is the perfect way to end your nautical adventure. Our local crew of sailing enthusiasts recommends the Crab Shell, with a stunning view over Stamford Harbor. Your Oyster Bay sailing adventure would not be complete without the live music, seating along the water, and plenty of cold drinks.

    Suggested Boats

  • This beautiful monohull will be an unforgettable experience
    $650

    This beautiful monohull will be an unforgettable experience
    Stamford, CT

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  • Enjoy extraordinary service from Greenwich CT to New York City!
    $720

    Enjoy extraordinary service from Greenwich CT to New York City!
    Greenwich, CT

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  • Move around Long Island Sound on this Egg Harbor 48
    $1,600

    Move around Long Island Sound on this Egg Harbor 48
    Stamford, CT

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Waterfront Restaurants in Greenwich, CT

Waterfront-Restaurants-Greenwich-CT
Sailing into Greenwich Harbor is an experience not to miss, with beautiful estates lining the coastline. For a romantic waterfront dinner after the perfect day on the Sound, tie up at the docks of the Delamar Greenwich Harbor Marina. Take your special someone to L’escale - a stylish restaurant with a French atmosphere, offering a creative Provencal menu and an extensive wine list. The service is impeccable and the view of Greenwich Harbor is impossible to beat.

    Suggested Boats

  • Set Sail Night or Day from City Island NY !
    $375

    Set Sail Night or Day from City Island NY !
    City Island, NY

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  • Charter boat for sightseeing, swimming, sunset cruise
    $375

    Charter boat for sightseeing, swimming, sunset cruise
    Stamford, CT

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  • Sail out of Greenwich Harbor on a classic Tartan
    $2,520

    Sail out of Greenwich Harbor on a classic Tartan
    Greenwich, CT

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Oyster Bay Sailing

sailing-oyster-bay
With plenty of things to do in Oyster Bay, a sail in the Harbor is an experience not to miss. Sailing past Center Island, you will pass Seawanhaka Corinthian YC, one of the first on the Sound. If you’re lucky, you’ll get to see Knickerbocker, a 95’ sailing yacht owned by Charles Dolan, and Vendetta, owned by Billy Joel. Oyster Bay is also the location of Sagamore Hill, the former residence of President Teddy Roosevelt. Make sure to include this escape on your summer bucket list.

    Suggested Boats

  • Relax on this 34' Najad Sloop while sailing the NY Harbor!
    $840

    Relax on this 34' Najad Sloop while sailing the NY Harbor!
    Port Washington, NY

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  • Beautiful Farr 33Racer/Cruiser waiting to create memories!
    $900

    Beautiful Farr 33Racer/Cruiser waiting to create memories!
    Old Greenwich, CT

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  • Cruise the Long Island Sound in class
    $500

    Cruise the Long Island Sound in class
    Stamford, CT

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Sunset cruise to Vanderbilt Estate

Sunset-cruise-Vanderbilt-Estate
William K. Vanderbilt II was an incredible yachtsman, and motor car enthusiast. He loved nature and the ocean, collecting marine life, birds, and other cultural artifacts from his travels which are all reunited today on the grounds of his former Long Island estate. The Spanish-Revival style mansion allows you to travel back in time to the historic days of the Gold Coast. As you sail past, you will notice his seaplane hangar, and will enjoy a view up the sloping lawn to this beautiful home.

    Suggested Boats

  • Enjoy extraordinary service from Greenwich CT to New York City!
    $720

    Enjoy extraordinary service from Greenwich CT to New York City!
    Greenwich, CT

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  • Speed around Greenwich Harbor and the Long Island Sound
    $2,520

    Speed around Greenwich Harbor and the Long Island Sound
    Greenwich, CT

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  • Sail out of Greenwich Harbor on a classic Tartan
    $2,520

    Sail out of Greenwich Harbor on a classic Tartan
    Greenwich, CT

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