Chesapeake Bay cruisers enjoy the fruits of Long Island Sound and Cape Cod while cruising in New England.

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The town of Cuttyhunk is quaint beyond belief. 

The Chesapeake Bay is a cruiser’s paradise. The relatively protected waters and diverse ports of call, from big cities to quaint waterfront towns, make it so. While the title “best cruising ground” could be debated endlessly, the Chesapeake Bay will always poll well.  

Happily, Long Island Sound and the nearshore waters south of Cape Cod are also contenders. And so, for many reasons, Chesapeake Bay cruisers have been drawn to Long Island Sound/Cape Cod and cruising “New England style.” Among the draws are a plethora of small-town ports of call, some islands that are the playground of the rich and famous, cooler summer temperatures, and lobster. Ah, lobster!   

As previously reported on these pages, the members of the Annapolis Yacht Club planned a New England cruise for this summer. In the last edition (September PropTalk), we reported on the trip up and first stop, Newport. There is so much more to tell.


After Newport, the cruisers headed to the tiny island of Cuttyhunk. The island has a typical winter population of 10 and a summer population of 350, including the many boaters who fill the lone marina and associated moorings. There is a yacht club celebrating 50 years featuring youth sailing for the summer crowd. The town is quaint beyond belief, including what looks like a backyard shed that serves as an ice cream shop (cash only and only about five or six flavors). 

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The Cuttyhunk dock and moorings are served by a crew that delivers lobster, clams, and more right to your boat.

Our stop at Cuttyhunk was supposed to feature an outdoor dinner with lobster as the main course. Unfortunately, the weather forecast 36 hours out was dire enough to force the cancelation of the much-anticipated lobster feast. Naturally, at the appointed time the weather was fine.

It mattered not. The Cuttyhunk Dock and moorings are served by another waterfront “shack” business that delivers lobster, clams, and more to your boat. Those deciding to pass on delivery could walk up the road a few hundred yards to a backyard pizza restaurant with just five outdoor picnic tables. 

The pizza master has a Bay connection. While he summers on Cuttyhunk and provides pizza to the hungry visitors, he spends most of his year as a teacher at the Severn School in Annapolis.

Martha’s Vineyard

Next stop was Martha’s Vineyard. This storied island has three possible ports: Edgartown, Vineyard Haven, and Oak Bluffs. Our large group of cruisers split up, with some in each port. Here we would spend a couple days and enjoy a group meal at a local yacht club, or so we thought.

In early July, the Delta variant of Covid-19 began surging in the US. There was a well reported outbreak, originating with Independence Day celebrations in Provincetown on the tip of Cape Cod. Provincetown happens to be in the same county as Martha’s Vineyard and Nantucket, our next stop. 

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Martha's Vineyard has three possible ports: Edgartown (pictured), Vineyard Haven, and Oak Bluffs. 

And so Covid caught up with us, again. The long-planned group events in both Martha’s Vineyard and Nantucket were prudently canceled by the hosts. The Nantucket Yacht Club shut down, likely for the season.

What do you do when Covid brings you lemons? Well, this bunch of cruisers made lemonade!

Our full group events on Martha’s Vineyard were canceled, but we were there. The cruisers masked up as appropriate, rallied, and hosted smaller group happy hours and outdoor meals at local pubs, restaurants, and the boats of fellow cruisers. The island was open and busy, restaurants were open and serving outside, masks were reappearing. 


Armed with our own impromptu Covid protocol, the cruisers moved on to Nantucket as planned. Nantucket has one large harbor for most visitors. It is, like Martha’s Vineyard, a summer playground for folks from the mainland, from Boston to New York. The town operates 125 moorings for visitors. The moorings were full and the dinghy dock congestion at a peak. The best-known ice cream shop still had a mile long line.

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Martha's Vineyard has three possible ports: Edgartown (pictured), Vineyard Haven, and Oak Bluffs. 

Like our experience in Martha’s Vineyard, Nantucket was generally open for business, despite the Covid outbreak in the county. The cruisers enjoyed additional small group gatherings in lieu of now canceled large group gatherings. The highlight of the visit was a quickly planned happy hour at the home of a club member, which happened to overlook the harbor and offered a spectacular sunset for the gathered cruisers.

After these two stops at the “high end,” it was time to get back to basic cruising. We were due back in Cuttyhunk for the rescheduled Lobster Feast. So back we went, 50 miles to Cuttyhunk, with lobster on our minds all the way.

Back in Newport

Our final formal stop was back in Newport. The venue was the tiny but legendary Ida Lewis Yacht Club. It did not disappoint. The cruisers gathered twice at Ida Lewis for afternoon happy hours. The food, drink, and comradery were excellent.

Afterward, many cruisers ventured on to local Newport restaurants and sampled their ever so interesting offerings.

The cruise started with more than 40 boats. By the time we got back to Newport for our final stop, the fleet had dwindled to a still sizable half that. Along the way many cruisers found it “necessary” to break off and reach further into New England, to explore even more distant ports while taking more time to enjoy a great cruising ground.

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One of the draws of "cruising New England style" is of course lobster. Ah, lobster.

You know what? You should go. Yes, you!  

Getting to Long Island Sound is not particularly complicated. The route for most cruisers is coastwise. This means up the Chesapeake Bay to the C&D Canal and down the Delaware Bay to Cape May. Following the coast of New Jersey with stops along the way brings you to and through New York Harbor and into Long Island Sound.      

At trawler speeds, the pleasures of Long Island Sound may be just five days away. Those of you who cruise at plus or minus 20 knots can be through New York Harbor and into Long Island Sound on the third day. 

The juice will be worth the squeeze, trust me. 

By Mike Pitchford

Catch up on Cruising New England Part I, the Draw of Distant Shores.