Coming from Block Island Sound, if we resist the temptation to stop off at Montauk Point for a little fishing, we can pass either north or south of Gardiners Island and on down to the southern end of Gardiners Bay to Three Mile Harbor.

Long Island chart

Three Mile Harbor is a shallow and protected anchorage (and a great spot for watching 4th July firework displays) at the southern end of which you can find marina accommodation - or the town dinghy dock - that will allow you to go ashore for a short taxi ride to East Hampton with its Atlantic beaches, boutiques and restaurants, and where you might even spot one of a number of celebrities out for a visit to their grand mansions in The Hamptons...

Sag Harbor

Heading west from Three mile harbor and round the southern end of Shelter Island, Sag Harbor is a popular cruising destination and often attracts yachts over 100' long.

Sag Harbor Broken Mast monument

Sag Harbor was originally a thriving whaling town, which even gets a mention in Moby Dick. There's a "broken mast monument" in the cemetery and many of the historic buildings date from the peak of this industry in the early 1800s.

Sag Harbor was actually the first official Port of Entry in the state of New York, established one day before the city of New York by an act of Congress passed July 31, 1789. At this time, Sag Harbor had more tons of square-rigged vessels engaged in commerce than New York City.

North of Sag Harbor, nestled between the north and south forks of Long Island, is peaceful Shelter Island, only accessible via ferry and a third of which is owned by The Nature Conservancy and intentionally kept in a wild state.


Circumnavigating clockwise around Shelter Island brings us to the northwest of the island and the ferry crossing point between Greenport on the "mainland" and Dering Harbor on the island.

Dering Harbor

Greenport is the eastern terminus of the long Island Railroad and is bustling and touristy, waterfront bars such as Claudio's being packed and boisterous in season - in complete contrast to Shelter Island opposite, where the peace of Dering Harbor prevails. Take your pick!

Almost completing our circumnavigation of Shelter Island, on the eastern shore we come to the slightly tricky entrance to Coecles Harbor (pronounced "cockles"). The buoys at the entrance are privately maintained and often move from year to year, but the shifting bottom bottom is only sandy, if your keel does wander...

Coecles Harbor

Inside, Coecles Harbor has a marina at its west end, with transient slips and moorings, but the natural harbor offers panoramic views and good protection at anchor in peaceful surroundings, the northern shoreline dotted with beautiful homes, the southern shore completely undeveloped and part of the nature preserve.

Orient Light

In order to get into Long Island Sound from Coecles Harbor, we head north up Gardiners Bay and through Plum Gut. It's best to time this passage at flood tide in order to catch a pretty good ride on the current going through into the Sound, leaving Orient Point Lighthouse to port.

Should you want to drop in and visit us at this point, Westbrook is just a short run northwest across the Sound. You can drop the hook in the protected anchorage of Duck Island Roads or come into our docks at Pilots Point North marina where you can expect a very warm welcome at both the marina and our office.

Northport power station Light

But if we're continuing west down Long Island Sound, we'll resist a stop in Port Jefferson and run on just a few miles further to Northport, easily recognized from miles away by the four red and white painted power station chimney stacks.


Northport is known for its old world main street (lined with ice cream parlors, antique stores and old-style barbershop) which still has embedded in it the trolley rails from the streetcars that brought people to the town from the railroad station in East Northport. Main Street ends right at the town docks and town green, site of many open air concerts during summer months.

With ice cream in hand, the cruising skipper can find a more peaceful and secluded anchorage immediately to the east in Oyster Bay where the west harbor offers 360 degree protection.


Our final stop on this quick visit to the north shore of Long Island is Manhasset Bay, just a few miles further west from Oyster bay towards New York.

With an open and easy entrance, but with good protection from prevailing winds, Manhasset Bay is as far west in New England as these few web pages will take us.

From here, we all set to wait for a favorable tide before a run down the East River, past the magnificent skyline of Manhattan and out into New York Harbor and points south...

For a more personalized itinerary for the cruising grounds of Long Island, please contact us.

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