City Island is a funny little speck of land at the mouth of the East River in the Bronx that once rivaled Manhattan as New York’s seaport metropolis. It is said to be the birthplace of oyster culture in the US, and was also home to a prominent shipbuilding community (boasting the production of 7 America’s Cup-winning yachts). Despite its storied past, City Island is now known as a quirky escape from NYC that is still located within the five boroughs. The shipbuilding industry dried up years ago, as did the oyster farming, and the seafood you order from the handful of restaurants on City Island Avenue is legally required to come from somewhere else due to the pollution in the river. While there isn’t a whole lot of variety on the island, there are a few good restaurants and bars, as well as a decent public library. It’s also a super convenient stop between the Long Island Sound and East River run through NYC.

We stop at City Island on our friend Phil’s excellent recommendation, where his friend Bobby sets us up with a mooring at Barron’s Boatyard. After getting squared away from our frigid trip through Long Island Sound, we meet our new friend Bobby and his fiancee Masha in town for drinks. We have a blast with them as they show us a few of the local haunts on City Island Avenue throughout the week, and also let us use their shower (thanks again, guys!), as Creeky’s water system is still a work in progress… Towards the end of the week we also meet up with my (Brendan’s) cousin Matt and his girlfriend Lucy for dinner and drinks.

The tides and currents favor an early AM departure from City Island to make it through Hell Gate at slack current, so we have a quiet final night in town, bid farewell to Bobby and Masha, and get to bed early. When we get started in the morning, the weather is perfect and we are excited to make our descent into Manhattan, but Creeky seems to have other plans. After starting the engine the voltage gauge is pegged at 16+ volts, which is then confirmed by multimeter. Shit… After some troubleshooting it’s confirmed that the voltage regulator quit. Bobby sends us to Bronx Ignition, which appears to be an alternator and starter specialty shop that is somehow still operating (and successfully, from the looks of it) as if it’s the 1960s. Not only do they have a voltage regulator for our ancient alternator, but they have the larger higher-output version as well — both on the shelf. The proprietor tells us about how this is one of his favorite alternators, and how they don’t make them like this anymore. Reassured, and now with a high-output alternator and a spare, we return to the boat, install the new alternator, and everything is running perfectly again.

A day later than planned, we leave City Island at around 8:30am, and resume our journey on a chilly and overcast day. We’re joined by local celebrity Ross, who provides some amazing breakfast sandwiches and donuts for 12 people from a bakery in Greenpoint, as well as invaluable local knowledge at every twist and turn on the East River. We had heard lots of threatening stories about passing through Hell Gate, but we time the trip well, and are past the fabled death trap by the time Ross casually points out, “…and that was Hell Gate.” Maybe it’s crazy if you catch it at the wrong time, but it doesn’t seem like it would be any worse than (or even comparable to) the Piscataqua River on most days!

Motoring down the East River, alongside NYC skyscrapers, under all 8 bridges, and past the Statue of Liberty is pretty thrilling. It’s kind of like driving a car through the heart of the city, with all of its hustle and bustle, but with no other cars on the road.

We travel parallel to FDR Drive, catching startled double-takes from onlookers who seem surprised to see a boat casually motoring through the city in early winter. Ross acts as a tour guide as we navigate through the Big Apple, seamlessly answering our questions with both fact and fiction. As we get closer to the southern tip of Manhattan we pass a Wall Street heliport that resembles a beehive, with a frenzy of private helicopters simultaneously arriving and departing in a chaotic symphony. This leg of the trip is truly surreal, but seems to fly by. Before we know it, we are passing by the Statue of Liberty, past a few Staten Island Ferries and other commercial traffic, then under the Verrazano-Narrows Bridge and into New York Harbor.

After dropping Ross off at a derelict boatyard in Coney Island, we head south across the harbor through some nasty chop, and into New Jersey. We drop anchor in Atlantic Highlands, NJ behind the seawall and enjoy another “state lines and bubbly wines” celebration.