Last month we reported on the planning and communicating complexity associated with a large group cruise from the Bay to some of the most iconic ports in New England. As you read this, the “fun” part is underway. Finally!

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It is a humbling experience to cruise past Lady Liberty. 

While many a Bay cruiser has visited New England by boat, the excursion by more than 40 boats and over 100 people calls for some serious planning. In the fall of 2019, a group of seasoned cruisers out of the Annapolis Yacht Club (AYC) initiated the planning for a summer 2020 cruise. You know what happened next. As the fall of 2019 turned into the spring of 2020 and after considerable cruise planning, the cruise leaders came face to face with the realities of Covid and canceled the cruise.

Ever the optimists, the cruise planners held out hope the shelved planning could be revived for a 2021 “do over.” They were betting that vaccinations would advance, and venues would open. They did!

The revived cruise covers 1000 miles and includes stops in Newport (twice), Cuttyhunk, Martha’s Vineyard, and Nantucket. Some boats left Annapolis in early July and some a bit later. The first stop for a full group rendezvous was Newport in mid-July.

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Humpback Whales off Barnegat Light. 

The travelogue so far, just halfway through the cruise, includes a tropical storm, boat issues, fog, whales, triathlon swimmers, and some great party venues. Let’s start with the weather.

While the active group gatherings and group ports of call are wedged into two weeks, the overall itinerary for some of the cruisers is half the summer. Slower boats and folks with extended plans began leaving the Bay in early July. Several of them then had to hunker down or delay departure as Tropical Storm Elsa swept south of Annapolis on July 8 and visited points along the route north and our intended destinations the next day.  

Perhaps the bigger weather story was fog, a New England staple. In the heart of the travels in Long Island Sound and to our first port of call, Newport, some AYC cruisers experienced days and days of fog. At times, the visibility was limited to a few dozen yards. Most boats in the flotilla moved ahead, albeit slowly and with radar spinning. It is a safe bet that every crew member became ever so much more familiar with their friendly radar screen.

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Harbor at Cuttyhunk Island, MA.

As we moved north, the wildlife changed. The birds change a bit. The dolphins we now occasionally see in the Bay continue up the coast. Just a mile off Barnegat Light, several cruisers spotted a pod of Humpback whales searching for lunch. You do not see that in the Bay!

When we left, the sea temperature in the Bay was approaching 80. In Long Island Sound it was more like the low 70s. The air temperatures followed suit. The very warm Bay area days finally gave way to highs in the 70s as folks worked through the fog and reached Newport, our first group event stop. Finally, it was cooler, as promised! 

The route for most cruisers was coastwise. This meant up the Chesapeake Bay to the C&D Canal and then down the Delaware Bay to Cape May. Following the coast of New Jersey with stops along the way brought us to New York Harbor. No cruiser could resist a slight course deviation to sail near Lady Liberty. It is truly a humbling experience.  

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The New York Yacht Club annex in Newport, RI.

There are a wide variety of great stops once through New York and into Long Island Sound. Much like the Bay, it is a cruiser’s paradise. One group of boats chose Mystic, CT, as a planned stop. An unusual departure delay occurred for them the next morning. The Mystic Seaport Museum was hosting the beginning of a triathlon, and 100 or so swimmers entered the water that morning for the first leg. The marine police closed the waterway until about 10:30 a.m.

And, of course, along the way some things broke. We are talking about boats!

One pair of intrepid cruisers found out one of the engines in their 36-foot trawler required major surgery. The schedule for the surgeons could not meet the schedule for the planned departure north. So, they borrowed their daughter’s 35-foot sailboat. This change of vessels required them to remind themselves along the way of their sailing days and sailing skills, perhaps a little rusty after years in the trawler life.

Another cruiser made it to Newport before developing a small leak in the high-pressure side of the diesel fuel line. As it turns out, the labor on this is an easy couple of hours. But the fuel line needed to be made up by a machine shop. So, they are staying in Newport an extra week or so to resolve the problem while checking ferry routes so they can join the group in Martha’s Vineyard and Nantucket.

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Enjoying dinner at a prospective member's home in Newport. L to R: Patty Baumiller, Ginnie Hurley, Cruise Leader Chuck Hurley, and AJ Whittle.

But all the weather and boat problems are worth it for the open water passages and the pleasure of friends at some fantastic venues. The first formal gathering was at the Newport home of a couple whose membership at the AYC is in process. The home, one of those “little” Newport summer places, had a party tent set up in the side yard to accommodate the crowd for a catered dinner and poolside seating with a view of the rocky Rhode Island coast for cocktails. This author did wonder if I was too old to be adopted…

The next gathering was at the fabled New York Yacht Club (NYYC) facility in Newport. They had been down to visit AYC a year earlier and were repaying the courtesy. The cruisers gathered for cocktails in a bar area that spoke of long-ago yachting royalty. At first there was a bit of rain keeping us in the bar, but it soon cleared, and we spilled outside for a fantastic view of Newport Harbor. A fine dinner followed which included the traditional presentation of the AYC burgee by the commodore to the NYYC. 

The weather did cause the cancellation of a planned outdoor lobster feast in Cuttyhunk that followed our stop in Newport.

Thunderstorms were predicted for the evening event. The forecast was compelling enough to cancel the event 36 hours ahead.  

Naturally, at the appointed hour, the predicted thunderstorms parted like the Red Sea, and we got no rain. Fortunately, we have a make-up date later in the month for this planned event (you can never have too much lobster). We will report on that and more in the second installment of this cruise travelogue. 

By Mike Pitchford

Visit How to Plan a Group Cruise to read Mike Pitchford's first article in this series.