New York, New York, Big City of Dreams

Heidi and her dad in NYC Harbor

The highlight of September had us sailing through Hell’s Gate, down the East River, and straight into the heart of New York City. With family aboard, we had a two day adventure, first spending the night in Brooklyn then moving on for a brief visit to Jersey City before tackling the rest of the coast of New Jersey on our way south.


But. About New York. We started in City Island, where we spent the night, provisioned and picked up crew (family). If you’ve never been to this little gem of a place, we can’t recommend it enough! Once you hit street level, you’re unmistakably in NYC, yet…you might also think you were on the Cape from time to time. Our mooring at the City Island Yacht Club had spectacular views of the New York skyline, and the friendliest and most welcoming people we’ve met in a long while. It’s a place for people who love their boats and the water and they’re so happy if you feel the same way.

The view from the City Island Yacht Club

Once the crew was aboard, we headed out on a hot, hot afternoon and slowly made our way past power plants and playing fields, LaGuardia Airport, the hulking horror that is Riker’s Island and into the heart of the city. Seeing it all from the deck of our floating home, surrounded by our loved ones, was next level awesome.

Into Brooklyn we went, where the end of summer was in full swing! The grilling, the music, the gorgeous green spaces full of families, all of it was a feast for the senses. We saw a baby yacht called EBITDA, which is all the reminder of a career in finance that Alex will ever need, and a gorgeous wooden boat called Rarebit which looked vaguely familiar. Later on, after seeing her owner (hint, a famous Welsh actor) carrying his trash and joshing with the very chatty dock hand, we remembered that there had been a great story in the NYT about her loving restoration. Only in New York.


Brooklyn delivered a HOT night’s sleep. In the morning we changed crew, taking on board four recent college graduates for an afternoon of trading tacks with Lady Liberty. What a thing to sail around those waters full of ferries and jet skis and cargo ships. After dinner at a JC ‘beach bar’ with the kids, we were on our own once again. An evening of laundry and US Open tennis on the TV at the Liberty Landing Marina capped off a perfect New York visit.


In New Jersey, the weather took a turn towards stormy. We decided to hang out for a night in Sandy Hook NJ, a quiet little anchorage by a Coast Guard base with a great sandy beach for dog walking where you can still see the skyline of New York. We thought we might have to be there for a couple of days, but the bad weather was less bad than we expected so we decided to push on after one night and head for Manasquan. The truth of the New Jersey coastline is that it’s long and there aren’t a lot of places to take your elderly poodle in for a walk. We came into Manasquan after a hectic day of sailing that Bill decided was not so fun. The remnants of a tropical storm churned up large seas that would be with us for days off of NJ.

In Manasquan, we poked about for a place to tie up in the harbor still surging with the outside swell. After several less than satisfactory stops at unwelcoming docks and some minor scratches to the dingy and her mothership, we found a home with the other Capitan Bill.

The next morning, with the sea state somewhat moderating, we headed off for Atlantic City. “Wind from the East, three days at least.” We surfed our way down the coast topping 9 knots at times.

Pulling into AC was an exercise in cognitive dissonance. Casinos to one side and on the other….the loveliest, most peaceful anchorage with a long stretch of white, sandy beach for Bill to run on.

After a good night’s sleep we were up and out early and headed for Cape May. The good ole Northeast wind kept coming and gave us the opportunity to sail wing on wing. We made it to Cape May quickly.

The anchor went down in front of the Coast Guard base, along with a dozen other cruising boats. We began to pay attention to boat names as we expected (and did) see those boats again and again as they too head south. The cruising guide and sites told us we weren’t to walk to dog on the beach on the base, but we took our chances and Bill got a nice stretch of his legs at sunset as the Coasties played Taps. Fortunately, neither the dog, nor his owner, were shot for trespassing on the Coast Guard base. Now that I think of it, its funny how often we anchor directly in front of Coast Guard bases. And also odd that so many of them have nice beaches on base for dog walking.


With our New Jersey adventure behind us, we headed up into the Delaware Bay. No wind–A big change, and hot hot hot. The bay is wide and brown and full of huge cargo ships and oil tankers and power plants, nuclear and otherwise. Finally, we took a left, into the C&D Canal, a Cape Cod Canal duplicate.

We spent a couple of nights in the Upper Chesapeake in small, still coves with southern country names like Cabin John Creek. At one point, we met up with our friend, Hattie, from JKU. Hattie sails Iris, an early 1970s Tartan 34 sistership to Fearless, a boat Chris once owned.

Sundance and Iris

And then down the bay and into Annapolis for an extended stay.

Annapolis is a sailing Mecca. We picked up a City mooring and settled in. The next few days had us taking turns exploring this historic city, touring the campus of the Naval Academy, catching up with Alex’s high school friend Mike, and his kids Bridget and Seamus, and attending a folk music concert that happened to be on stage a stone’s throw from our cockpit. (Madison Cunningham & Amos Lee)

As luck would have it, we were in Annapolis on Defenders Day, a Maryland holiday that marks the battle during the war of 1812 that inspired the writing of the Star Spangled Banner. In Annapolis, every day feels like Defenders Day because they play the Star Spangled Banner at the Naval Academy at 8AM every day. Points off if you are still sleeping.


With the boat once again well stocked with food and fuel, and her crew on the ready with clean laundry and a fully stocked liquor cabinet, we were off for the Eastern Shore of the Chesapeake, and the intracoastal waterway route south from there.

Enjoying a Pain Killer in Annapolis on Defenders Day

5 thoughts on “New York, New York, Big City of Dreams

  1. What a marvelous journey! I enjoy your photos and reading about places both foreign and familiar from another point of view!

  2. A good read. I’ve been logging with envy the powerful Nor’easters that eased your way south at that time.
    We just learned our “still schooling” friend Eben is staying at Liberty Landing Marina for the semester so we’ll be replicating that part of your trip! I take it that NYC was motoring? All our best, Will + Tasha

    1. Motoring in NYC for sure. But then some great sailing off of NJ. That’s open water out there and can be a slog with a headwind or a rolly motor with no wind so we jumped all over that tail wind we got even tho the seas were pretty intense. That stuff doesn’t show up well in the camera but it was wild out there. Enjoy your ride!

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