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My list of North Shore harbors on Long Island
I'm not a professional cruising guide author, but I have some opinions...
Best scenic harbor on Long Island's North Shore: Agreed, it's Oyster Bay (it gets a three star rating out of three stars).
Good points: You can easily sail into Oyster Bay and sail around Centre Island (it's more like a peninsula) until you end up in a popular anchorage area. You can stay on a guest mooring at the Sagamore Yacht Club. You can sail around in Oyster Bay on a windy day and avoid the larger waves of the Long Island Sound.
Downside: It's a little bit of a walk to the town and restaurants, but not too bad.
My favorite harbor on Long Island's north shore is Greenport (three stars). OK, technically it is on Long Island's north fork... Greenport town (three stars) is a boater's dream with easy walking access to restaurants, shops, laundry, even ship's hardware and even a carousel on the waterfront. There are multiple solutions for docking in the town.
The nearby Stirling Basin (three stars) also has multiple marinas with docks, pools, and moorings. A short sail can bring you to Shelter Island (three stars). Sag Harbor (three stars for the harbor and three stars to the town of the same name) and Block Island are worthy destinations that are also within reach.
My comments on the choices for "runner up":
Cold Spring Harbor (three stars) near the village of the same name is a scenic destination with some popular beaches available to a boater. Beware the shallow depths at the south end of the harbor.
LLoyd Harbor (three stars), on the way to Huntington Harbor, is a very popular destination for anchoring.
Huntington Harbor (two stars) has a very large concentration of moorings, slips, marinas and yacht clubs. There are restaurants and a West Marine toward the south-east end.
Price Bend (two stars) in the northwest corner of Northport Harbor is a popular destination with beaches nearby. Duck Island Harbor (three stars) is nearby and worth a detour, also a pretty destination.
The northeast corner (two stars) of Northport Harbor attracts anchoring boaters, but the power plant is a large visual distraction.
Further south in Northport Harbor (three stars) is the lovely town of Northport (three stars) with easy access by boat. Get there early enough and you might get a slip on the town dock.
Going west gets you to Hempstead Harbor (no stars), which is a bit too industrial for my tastes.
Further west is the lovely Manhasset Bay (three stars) with what has been described as the single largest population of boats in New York State. In spite of that, you can sail within the bay. There are multiple sources of marinas, yacht clubs, moorings and slips, including multiple restaurants with slips for their lunch or dinner patrons on the Port Washington side. A West Marine is a moderate walk from a marina in the northeast corner of the harbor. The town of Port Washington (two stars) has lots of restaurants and shops, but you will probably want a taxi for the trip to and from.
Turning east, Port Jefferson Harbor has good options for anchoring in the northwest corner (two stars), along with marinas, moorings and slips. The town launch can bring to the town of Port Jefferson (three stars) with lots of restaurants and shops. The northeast corner (two stars) is a popular destination with the beach nearby.
Further east, the Mattituck Inlet (two stars) leads you into the Mattituck Creek (three stars) which is quite possibly the most beautifully scenic river I've ever seen anywhere near Long Island. Marinas appear at either end and there is a town dock at the south end - but nothing within walking distance that I know. A restaurant in the Mattituck Creek had dock space for patrons.
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