Things to Do by Boat in Oyster Bay and Connecticut

Explore the waters of Connecticut and the Long Island Sound

At the far western end of Long Island Sound, planning a sailing trip from Connecticut or Oyster Bay is one of the best things to do around these parts. Enjoy great sailing, fantastic fishing…. And of course, oysters!


Long Island Sound is blessed with a great selection of waterfront towns, perfect for a sailing trip on one of our beautiful yacht or boat charters. Towns like Greenwich, Port Chester and Stamford on the Connecticut side, or Oyster Bay, Port Washington and City Island at the New York end all have an amazing choice of Sailo boat rentals. 


The town of Oyster Bay itself straddles the full length of Long Island, and is known for its history and tradition for sailing activities. A favorite hangout of Teddy Roosevelt, with the former president visiting regularly and having a summer home in the town, this charming town is also his final resting place, with both he and his wife Edith buried in the local cemetery. 


Sailing into Oyster Bay is a great way to see the town, and you can easily reach the harbor on a day trip from one of the Long Island Sound ports such as Stamford or Greenwich. You’ll also find a selection of boat rentals in or around Oyster Bay itself, perfect for a weekend excursion. 


If you enjoy sailing your private charter or relaxing on deck while your captain does the work, you’ll find Sailo has a boat rental for your needs. Take a trip for the day aboard a beautiful sailboat, enjoy casting your line on a fishing trip or experience the high life aboard a powerful motor yacht charter. Check out the boats and find your dream rental in Oyster Bay, Connecticut or the greater Long Island Sound area.

Total Marine LTD

The Ponus Yacht Club

Cummings Park Marina

Seawanhaka Corinthian Yacht Club

Cove Island Park Marina

Glen Cove Yacht Club

Glen Cove Anglers Club

Ebb Tide Marina

Rudys Tackle Barn

Grass Island Marina

Orienta Yacht Club

Greenwich Boat & Yacht Club

Mamaroneck Bch Cabana & Yacht Club

Greenwich Point Park Marina

Halloween Yacht Club

Stamford Yacht Club

Delamar Greenwich Harbor Marina

Stamford Landing Marina

Oyster Bay Marine Center

Harbour Square Marina

Hempstead Harbour Club

Glen Cove Marina, a VMG Marina

Indian Harbor Yacht Club

McMichael Yacht Brokers

McMichael Rushmore Yard

Derecktor New York

The Waterfront Center

R. G. Brewer

Avalon on Stamford Harbor

Roosevelt Memorial Park Marina

Brewer Post Road Boat Yard

Delamar Greenwich Harbor Marina

Brewer Yacht Yard at Glen Cove

Old Greenwich Yacht Club

Sagamore Yacht Club

Jakobson Shipyard Inc

Brewer Yacht Haven

Catalano & Sons

Nichols Yacht Yard

New York and Connecticut fishing charters


The waters of West Long Island Sound are teeming with marine life and are perfect for a day out on the water with your fishing rod in hand. You’ll find striped bass, bluefish, false albacore (a species of tuna) and fluke in the clean waters of the sound.
Thanks to changes in environmental laws over the years the water quality has improved and today, fish stocks have been increasing. So, you might just reel in your dream catch on board your Sailo fishing boat charter!


    Suggested Boats

  • Climb aboard 21’ Sailfish to explore Fantastic New York
    $872 (per day)

    Climb aboard 21’ Sailfish to explore Fantastic New York
    Port Washington, NY

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  • Unmatched Northeast Angling Experience
    $550 (per ½ day)

    Unmatched Northeast Angling Experience
    Milford, CT

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  • Enjoy a Fun-Filled, Action-Packed Day of Sport Fishing
    $684 (per ½ day)

    Enjoy a Fun-Filled, Action-Packed Day of Sport Fishing
    Clinton, CT

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Sailing in Huntington and Northport Bay


On the north side of Long Island, Huntington Bay is a truly stunning place to discover on your own private boat rental. Sandy beaches, protected nature reserves and quaint towns and villages make this the perfect place to explore from the water. With a boat rental from Oyster Bay, Huntington or Stamford, take the time to sail past the Vanderbilt Estate in Northport Bay and marvel at the Spanish revival splendor. Or if you prefer, moor your boat and explore Caumsett State Park and get away from the hustle bustle. 

    Suggested Boats

  • Move around Long Island Sound on this Egg Harbor 48
    $1,600 (per ¼ day)

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

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Connecticut coast hopping


As one of the six New England states, Connecticut is one of the best places to explore by boat rental. Coast hopping anywhere from Port Chester or Greenwich; to Stamford, New Haven and Milford, there are many towns, villages, bays and beaches to discover. Enjoy the view from your private yacht charter, or if you’re looking for the best things to do, take the time to stop and enjoy nature reserves, local hospitality and arguably some of the best seafood in the country.

    Suggested Boats

  • Enjoy extraordinary service from Greenwich CT to New York City!
    $1,100 (per ¼ day)

    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 (per ¼ day)

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

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Sailing in Oyster Bay


When it comes to things to do in Oyster Bay, of course, enjoying the sailing and the maritime activities is high on the list. If you’re sailing into Oyster Bay, or choosing a boat rental in the town, head to the Theodore Roosevelt Memorial Park and enjoy the breathtaking scenery of the bay. Walking the waterfront here you’ll be able to see what brought the president back time and time again. And of course, don’t miss the delicious local seafood at one of the many great restaurants in Oyster Bay, such as Canterbury’s.

Sunset cruise in West Long Island Sound


Romantic excursions don’t come much more unforgettable than a private sunset cruise. If you’re looking for something memorable to do for a loved one, or to treat your friends or family to something special, you’ll find plenty of options to choose a sunset cruise in West Long Island Sound. In Greenwich or Stamford, CT, or City Island or Oyster Bay, NY, there are yacht charters suitable for couples, or big groups to make the most of that incredible Long Island by boat rental sunset!

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