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New York to Annapolis

Updated: Nov 19, 2023

Gale Force Winds

The weather never looks that bad in pictures.

As we sit on anchor, stuck in the boat, in Bermuda, braving a gale with winds reaching up to 45 knots, I decided it was time to catch up with the blog. The howling winds and building waves around our boat have me white-knuckling the keyboard. I’m hoping working on this is a good distraction!

Our last blog entry had us sailing back to New York. A lot has happened in between.

The Exclusive Fishers Island

Fishers Island (Photo taken by

After leaving posh Newport, Rhode Island we sailed to our friend's island, Fishers Island. Fishers Island is a small island located at the eastern end of Long Island Sound, situated between Connecticut and Long Island, New York.

Fishers Island may not be breaking any records for size, but what it lacks in acreage, it makes up for in charm. It is a 9-mile stretch, just 1 mile wide, and only accessible by boat or private plane. It boasts pristine beaches, summer mansions, and exclusivity so thick you can practically swim in it.

The World According to Garp house is on Fishers.

The majority of the island is managed by the Fishers Island Development Company (FiDCO), a private organization much like an HOA. To get anywhere on the island you have to be with a member. We are lucky enough to know the most awesome year-round residents (my college buddy and her husband) and were excited to visit in our very own boat!

Usually on Fishers, we reenact the Big Chill (I'm dating myself with that reference) when about 6 of us Potsdam ladies get together with our spouses and sometimes children and raise a ruckus! This time is was just Dave and me.

It was more chill and less big this time. Gail and Greg were a bit under the weather, the old Covid bug was rearing its ugly head again! However, they rallied and we did all the highlights-beach bar-b-que, fishing for bass, and hanging out in their gorgeous home and backyard.

We also went to America (Connecticut) where Dave and I enjoyed grocery shopping in a fully stocked store! The only thing missing was dancing at the Pequot. It was closed this year due to an "Inconsiderate House Guest" i.e. a badly behaving drunk visitor!

It was just really great getting to spend time with old friends again!

Port Washington

After a relaxing Labor Day weekend on Fishers, we motor sailed through the Long Island Sound with a course set for New York City. We were headed for Harlem but as we approached the mooring field, a 38-foot motor cruiser blew up at the gas dock spewing smoke and debris everywhere. We diverted to Port Washington, Long Island. It turned out to be a lovely place for cruisers!

We grabbed a mooring ball and water taxied in. On Port Washington's Main Street, we found charming boutiques, seafood restaurants, a West Marine and a Target! All in walking distance. Another short walk uphill and we arrived at the Long Island Railroad Station. The LIRR was a pleasant way to get into the city. We liked it so much, we went two days in a row.

Sunset from Port Washington

The City That Never Sleeps

We hoofed it around New York City, doing the tourist bit. First stop: Rockefeller Center. I played cheerleader for my striking union pals who were marching around outside.

In the summer, you can roller-skate on the rink—fun, right? Too bad it was closed that day.

Next up, paying respects at the 9/11 Memorial. I kept calling the skyscraper the Freedom Tower, confusing poor Dave. Surprise, surprise! In 2009, NYC rebranded it One World Trade Center. Apparently, I missed the memo on that one. Word on the street was the public generally thought Freedom Tower was a cheesy name.

We also visited the NYC Public Library. Disappointment struck when we discovered we couldn't dive into the sea of actual books, those were in rooms guarded from the tourists snapping selfies. Instead, we meandered through ornate hallways and admired fancy drinking fountains.

Off to the Museum of Natural History, where being New Yorkers meant the privilege of setting our own admission price. We didn't go full "free," but we did negotiate a sweet deal (less than their "suggested" price).

Central Park

After a rain-soaked stroll in Central Park, we beelined it for McSorley's, NYC's oldest watering hole. It’s a pretty easy bartending gig since they only have two choices of drink-light or dark. It's a time capsule from 1854—smells like history, or maybe just really old beer. Legend has it even Abe Lincoln dropped by for a pint after a speech!


Then, the subway saga. Someone got in the way of a train, and suddenly we were stuck in the belly of the beast. A not-so-gentle reminder of why we're not city folk. Eventually, we managed our way back to Grand Central. Thankfully, the LIRR was a ghost town. I was officially maxed out on the Big Apple's human hustle and bustle

Grand Central

September is Hurricane Season

With a hurricane hot on our heels, wind or not (spoiler alert: not), we bolted for Annapolis.

We have mastered the art of timing currents and we zipped through the East River, easily navigating through the treacherous Hell Gate. Although it was a bit smoggy that morning, we enjoyed viewing the iconic skyline up close and personal. We had taken this route 4 years prior and it was nice to reminisce. We popped out at Lady Liberty and headed south.

We zoomed past the entire state of New Jersey, and my night watch kicked off right as we glided by the dazzling lights of Atlantic City. The highlight of the trip was Dave catching a Mahi Mahi which we enjoyed and shared along the way.

Dave's big Mahi Mahi catch!

We cruised into Delaware Bay, then gracefully slipped through the Chesapeake and Delaware Canal. It felt a lot like we were back on the Erie Canal. And just to prove how slow sailboats move, we were outpaced by a dad and his five-year-old on bikes, casually pedaling along the canal path. Yep, that happened.

The Chesapeake Bay Bridge

We anchored for a night in the C&D canal then pulled into Annapolis bright and early on September 12th.

Unknowingly, we ended up anchoring directly in front of our friend Kurt’s marina in Back Creek Bay.

Our very convenient anchorage in Annapolis.

It’s fair to say that we whooped it up good in Annapolis!

Friends, Friends and More Friends

Part of the I Dock Crew from Sodus Bay!

Part of our friends’ group from I Dock at Katlynn Marina in Sodus Point, NY had migrated to Annapolis. Kari and Dave on Selwai, our old boat neighbors, had left the year before for Kari’s job in Washington, D.C.

Kurt had bought a new boat in Norfolk and relocated up the Chesapeake in the marina next door to Kari and Dave’s. When Lagerhead showed up, it was quite the surreal experience of all of us together again with our boats in a new location!

We celebrated Dave’s birthday there and Kari’s birthday a week later!

Kurt, Dave, and I hit up the Inaugural Annapolis Baygrass Festival, grooving to our favorite bluegrass tunes for a solid two days.

We had a lot of fun with Kurt. We were Three Muskateering it all over town.

We also reunited with more Katlynn Marina pals at the Annapolis Motorboat Show. We had a riot with Mike and Kim from the trawler Steadfast, chilling at their posh rented mansion with their hilarious motorboat crew.

We caught up with friends, Pauline and Remy and their adorable daughter, Indah. They treated us to a fabulous lunch at the Boatyard and we walked around town together enjoying their company. We took a quick peek at the Motorboat Show as well.

Mark and Terri, friends from Bras d’Ore lake, sailed in for a night of fun before jetting back to Ontario, Canada.

Annapolis Sailboat Show

Annapolis was also calling us for the Sailboat Show, a tradition we've attended for the past two years. We were stoked to see even more old friends from Rochester.

The rest of I Dock descended for the show, including Kevin, Michele, and Joanne. We had a blast exploring Washington DC together and crashing at Kevin and Michele’s swanky Airbnb.

Dave Goes and Goes until.....

The cherry on top was reuniting with Craig and Anne from Rochester, who were on their own travel adventure by train. We caught up over lunch at Pusser’s during the show, soaking in the joy of old friendships.

Don and Jan joined the chaos, and we managed to squeeze in a delightful breakfast chat before the Saturday show. We shared a homemade Pop Tart that was out of this world! We swapped tales of adventures, boat projects, and dreams of rendezvousing in the Caribbean in 2024.

The absolute highlight was when Jack and Melly rolled into town! We were seriously missing our dynamic duo and seeing them was almost tear-inducing. The bonus? I hitched a ride back to Rochester with them, enjoyed the royal treatment at the Jesmers, I was only in Rochester for one night. It would have been nice to catch up with friends there too but I ran out of time.


The next day my sons and I drove out to Saratoga Springs to visit with my mom and both my brothers. I stayed a week and had a wonderful visit!

Hotel California

We got very spoiled anchoring so close to Kurt. We'd zip over to his boat, enjoy the luxury of his marina's showers and laundry and his fun companionship. Amazon deliveries? Sent straight to Kurt's. We made friends galore, both at anchor and in the marinas.

And let's talk about Kurt's truck – a real opulent item! Grocery hauls and leisurely visits to all three marine stores were just so easy. We even took it on a road trip to Baltimore, all in the name of stocking up at the holy grail of Wegmans.

Annapolis was starting to feel a bit like Hotel California – you check-in but will you ever leave? Such a lovely place.

There are so many boat jobs to do, we could have stayed another 6 months.

Saga and Lagerhead sailing together!
Kurt sailing on Halloween!

Moving Day However, after a solid 8 weeks of Annapolis bliss, we finally broke free on Halloween, with Kurt (sporting a Halloween mask, no less) as our buddy boating companion. Down the Chesapeake we sailed, bound for Norfolk.

Now, Kurt's journey could fill a blog all its own, chronicling the epic Saga of everything that went awry with his boat. We shared anchorages for a couple of nights, dining aboard Lagerhead each evening and swapping stories.

Then came the bittersweet farewell – we were gearing up for a daring dash from Norfolk to Bermuda, while Kurt charted a course down the Intracoastal Waterway, aiming for the charm of South Carolina.

And just like that, our paths diverged, each boat with its own tale to tell. The adventures continued, and the sea beckoned us forward!

We will miss all our wonderful friends and family and wonder when will we all meet up again?!

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