One way to get through a cold Chesapeake winter is to plan a summer cruise. The very effort will warm you up! And so it was, in the dark days of February 2022, three Chesapeake Bay area couples began to plan in earnest for a summer cruise to a distant shore: in this case a circumnavigation of Long Island Sound.

long island sound
And so it was that three Chesapeake Bay couples planned a cruise to a distant shore. (Gimme Shelter and Celerity flying along on the Sound.)

As the itinerary evolved, the result was three weeks on the boats, beginning with the Independence Day holiday weekend. 

Getting through New York Harbor and into Long Island Sound is a 240-nautical-mile-run from the Annapolis area. Our plan was to push hard to get to Long Island Sound and then slow down and enjoy the many interesting ports in the Sound, before a reciprocal hard push back to Annapolis, as our allotted three weeks drew to a close.

On a 20-knot boat, weather permitting, you can make Cape May your first stop (112 nautical miles from Annapolis). Mother Nature favored us, and the first leg was easy. The three boats got an early morning start and were in Cape May by midafternoon. Spirits were high at our group dinner ashore that evening. After a winter of planning and a spring getting the boats ready, it was a common and palpable relief to be underway.

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Eric and Shelley Rubin pose on Gimme Shelter in front of Lady Liberty.

The next stop presents a choice to folks making the trip to the Sound. You can push ahead for an even longer day, to a location inside New York Harbor, maybe 125 miles. Or you can hold up short, stopping along the New Jersey shore.  

For us it was the latter. We stopped at Manasquan Inlet at a marina in the town of Brielle. Manasquan Inlet is 88 miles from Cape May and provides an easy shot, less than 40 miles to New York Harbor.  

After a not too early start the next morning, we were loitering in front of the Statue of Liberty before lunchtime. The brief slowdown was to allow for the almost mandatory photo of your boat with Lady Liberty in the background. How can you resist?

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Cindy Whittle, AJ Whittle, Shelley Rubin, and Sue Pitchford hunker down in the launch.

After cruising through New York Harbor and up the East River, we entered Long Island Sound in early afternoon. After the hustle and bustle inside of the big city, entering the Sound is a revelation. The traffic diminishes, the skyline turns from tall buildings to trees, the water turns ocean blue/green, and fresh air abounds.

Our first stop in the Sound was Oyster Bay. We were directed to our mooring via VHF just as some rain set upon us. The launch serving the moorings came to bring us ashore. Of course, the worst of the rain pelted us on the way in.  

One thing you will learn on a trip like this is that the preferred, by far, summer job for local high school and college students is at the marinas. The Oyster Bay marina/launch crew affirmed this when asked with a big smile on their faces. 

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Happy launch crew in Oyster Bay.

Another thing you may learn, or relearn, is how to pick up a mooring. Unlike the Chesapeake, moorings are omnipresent in the ports along the Sound. The problem is not just picking the lines out of the water from a high position on the bow (hard enough). You also need the divine helm sense to know where the mooring is once it disappears from your line of vision, under the bow. Usually, the designated bow crew can point, or wildly gesticulate, trying to vocalize something unintelligible, while facing away from the helmsman.     

While we managed to do okay in the mooring department, my hero in the mooring field was the captain of a large Grand Banks Eastbay who picked his mooring up singlehanded. As he approached his mooring, he stepped out of the side door with a remote control in his hand and walked to the bow. He deftly thumbed the remote until he could easily lean over the bow rail and snag the mooring line. Easy peasy!     

Of the three boats on the trip this was essentially the first long cruise for two, as the boats were newish to the owners, having been purchased the winter before. As such there were little “bugs” to work out.  

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Eric and Shelley Rubin on the to-be-cut foam mattress pad.

On one boat it seems the mattress in the master cabin was a bit firm. The crew had a solution and ordered a two-inch foam mattress pad for delivery at our second stop in the Sound—Port Jefferson. After we tied up at the chosen marina, they retrieved the foam pad from the dockmaster and proceeded to cut it to shape on the dock. It was a group effort worthy of a comedy skit. After the cutting and remaking of the berth, no small task on a boat, there were no more complaints about the mattress!  

Port Jefferson is a great little town to visit. One way to measure greatness of a port of call is the number of ice cream shops available to visit. I think Port Jefferson has half a dozen. That gets top billing on this trip.

Our next stop was Sag Harbor. Here our small fleet was dwarfed by the “big iron” in port. Sag Harbor is a very busy little town with beautiful people and expensive cars. Yes, they did have a couple of ice cream shops!

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Ice cream shop in Port Jefferson.

We planned our next stop to be the quaint Shelter Island Yacht Club. It did not disappoint. It was a very pleasant afternoon with a crack club launch crew who motored the launch over to the assigned mooring and handed the lines to you (who needs a remote control?). 

That evening over dinner at the club we had some weather decisions to make. Our planned next stop was to be Cuttyhunk, a small island at the end of the Elizabeth Islands, part of Massachusetts. Forecasted winds and ocean swells would make our trip less than comfortable. We elected to punt.

To make up the time we had designated for Cuttyhunk we added a stop in Greenport, NY. Here we found a nice little town, a bit more grounded than Sag Harbor. It also had a top notch, transient only, municipal marina. The restaurants were great, as was the ice cream!

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A stop in Mystic, Connecticut. 

From Greenport it was time to turn back west and to sample the Connecticut shore. We spent a couple of days in Mystic, taking in both their stellar aquarium and the Mystic Seaport Marina. We also stopped in Essex and Milford. Essex wins the “best manicured” award for a town with nothing out of place, at least on our morning walks. Milford tops the best ice cream category with a shop adjacent to the municipal marina called Scoopy Doo’s.  

From Milford we made a couple of short hops to ports back on the north shore of Long Island, Northport, and Port Washington. Like all our stops, they were nice little towns with restaurants, shopping, and of course, ice cream.

Completing the circumnavigation we retraced our steps through New York Harbor, where we just dodged a significant thunderstorm, and then along the New Jersey coast, through Cape May, and home to the Bay. Altogether it was about an 800-mile trip with 14 stops (and 14 new ice cream opportunities). 

My suggestion, start planning your trip up there some cold night this winter. You will love it! 

By Mike Pitchford