I was never supposed to take my boat through New York City. After getting sucked backward through the Cape Cod Canal on my way south from Maine, when the speed of the current exceeded the maximum speed of my little electric auxiliary, I wanted nothing to do with Hell Gate and its even faster currents.

In fact, whirlpools and ruthless ferry boat captains would wind up being the least of my worries. But this was the furthest thing on my mind as I lay at anchor in Lake Montauk over 100 miles east as the crow flies of the Big Apple on the tip of Long Island’s south shore.

It was not quite late October, and I was trying to secure my boat, Teal, a 1962 Tripp 29, in time for a delivery I was scheduled to do to Bermuda. I was also still shaking things down after buying Teal sight unseen in Maine a few months earlier. The plan was to fully refit the boat on the Chesapeake.

In the meantime, I had already singlehanded her across the Gulf of Maine and through the waters of New England. It had been warm, but the weather was now changing.

Six hours before I was supposed to ride the outgoing current around Montauk Point and sail along the south shore of Long Island, I got word that the owner of the yacht I’d planned to help deliver had contracted Covid at the Annapolis Boat Show, which meant the delivery was cancelled.

With a deadline no longer looming, I hit the snooze button that morning thinking there would be plenty more opportunities. However, in retrospect, I should have taken that weather window because a better one would never come. Either that or I would never quite catch it. If New York never sleeps then maybe a sailor should also never sleep in on New York waters, because sleeping through that one tide would eventually result in my having to tack back and forth across the western end of Long Island sound in December, at night, alone, still on my way to Hell Gate. I felt like Rip Van Winkle. But I’m getting ahead of myself.

As I woke from my nap, a stiff southwest breeze was ushering in what would be the last summer-like day on land as 7ft waves sprang up at the sea buoy. By the time it switched north again it was well after midnight and the seas didn’t lie down until the following day, at which point the wind began to clock into the west, then southwest. Rinse and repeat.

By now there was also a low a couple of days away, and I was officially becoming afraid of my inability to make headway into whatever weather it might be bringing. There would be no safe harbors for a hundred miles once I was offshore. I felt like I was watching the wind so closely the weather systems were blowing right past me. Or were the weather windows getting smaller? No matter. I had to keep moving or risk being pummeled by a Nor’easter while still at anchor. I, therefore, decided to divert onto Long Island Sound.

Before I could even say “Hell Gate,” though, there was Plum Gut, right next door to The Race, where Long Island Sound and Fisher Island Sound meet the Atlantic. I figured if I tacked my way through Gardener’s Bay I could anchor in the lee of Orient Point State Park, sail up to the gut at dawn at slack tide and either short tack my way through or use the auxiliary.

The forecast called for 5-10 knots out of the north-northwest, but it was more like 15-20 knots as I made my way to Orient Point. I figured the wind would be dead at dawn, but as soon as I came out from behind the protection of the thin, sandy peninsula there, a blood red sunrise revealed white caps to port just on the other side.

Clearly, I was not going to be able to get through the gut, so I eased out the main and turned back downwind toward where I’d anchored. I was now making hull speed as the giant Cross Sound ferry overtook me and a myriad of other high powered craft plowed past as well. I couldn’t believe I had ever actually thought I was going to be able to tack my way through Plum Gut, never mind Hell Gate. I could still see Montauk Point 13 miles to the east. After the storm, I’d sail back and try again to go offshore.

I sailed into Shelter Island Sound and immediately met some local yachties who turned me on to a mooring in a secure cove before I could even call my parents and tell them I’d just pulled into a safe harbor a 15-minute drive from where they still live in my hometown.

With plenty of friends and family aboard, two back-to-back gales passed quickly. I watched in awe as a 50-knot system blew through. After that came the year’s first cold snap accompanied by a dead calm. Doing my best to stay warm, I passed the time finding a diver to scrape the bottom (which had gotten horrendous again since I’d cleaned a colony of full-sized mussels off in Maine), installing a new VHF antenna, tuning the rig and generally trying to mentally prepare myself for what was now going to be a mid-November attempt at an offshore passage on my unfinished boat.

A short while later, underway again in the wind shadow behind Orient Point, I caught a brisk northwesterly toward Montauk flying dead downwind with a single reef in the main and a second one likely needed. It was now nearing the end of the day, and I realized I really did not want to have to deal with these kinds of winds offshore. Nor did I like the idea of having to stay awake the next 24 hours when I also had the option of simply daysailing down Long Island Sound. Tacking down the sound would give me a chance to practice my boat handling skills, I told myself. I’d deal with Hell Gate when I got there.

Disengaging the self-steering gear, I grabbed the tiller and fighting the weather helm aimed for the entrance buoy marking the jetties, back into the Montauk inlet. After that, I dropped the hook and sail and went back to sleep. I think I cried a little. I was sailing in circles, afraid of going back out onto the open Atlantic alone.

They call Montauk “The End,” but it was beginning to feel more like “The End of the World,” compared to just two weeks prior. I was now literally the only boat there. Even the sport fishing boats had all cleared out. Worse yet, it didn’t take long before the wind was up to its old tricks again as it swung back to the west, which meant I would have to go through the Race. Heaving-to on Block Island sound I waited for the tide to turn in the afternoon then reached my way officially into the Long Island Sound. My celebration was short lived, though, as I was soon tied to an alarmingly small mooring buoy on Fischer Island while a front dragged through bringing winds of 50 knots.

A secondary low wasn’t far behind, but I was determined now to try and move my keel at least a little every day, and immediately set out for New London, where I picked up a mooring on the Thames River in front of the bark-rigged Coast Guard cutter Eagle. I actually missed the buoy on my first try and had to power back against a stiff breeze, making barely 2 knots with a lee shore a short distance astern. When I finally caught hold of the mooring pennant, a fisherman on land and the crew of passing yacht applauded.

From New London, I sailed to Mattituck where the fall foliage was now on full display. After that came New Haven where I had to navigate a maze of breakwalls and tankers, then the Housatonic, where I had to emergency anchor in an oyster bed as darkness fell and the temperature plummeted. Port Jeff was next, followed by Thanksgiving dinner at my brother’s house in Huntington Harbor, where my niece and nephew didn’t believe me when I told them I was an adult.

I could see the city now, but as the sound narrowed, the traffic increased, and the wind fell light again. Daylight was also in short supply, and the temperatures had begun to regularly dip below freezing. In the end, I had no choice but to transit the Western Sound at night, since it was the only time the wind and tide were in my favor.

The southwest breeze brought a balmy feel to the early December evening as I sailed hard on the wind toward Port Washington. I didn’t mind having to throw in a number of tacks as well, as the waves were flat, and Teal was moving along at 4 knots. The water lapped against the hull, the lights of Manhattan twinkled up ahead, as did the last of the stars I’d be seeing until I got to the other side of the city. I was in my own little world.

Too much so, it seemed. When I picked up what I thought was a mooring in the dark as a gale built out of the open side of the harbor a very angry man came to tell me I was on a winter stick not a mooring. I looked around for another place to anchor, but there was nothing, so I opted for the protection of a little canal of sorts behind the marina a few hundred yards away.

After tying up to a dilapidated dock filled with derelict boats, I charged my motor batteries for 30 hours using my Honda Generator, so they would be at the fullest capacity and capable of giving me 3 knots of boatspeed for three hours.

An east wind made the last few miles to the Throgs Neck Bridge a run. Anchoring in a shallow cove between Throgs Neck and Locust Point, just off SUNY Maritime I hoped my anchor wouldn’t foul. I was one and a half miles from the East River.

It may have taken me weeks to get upwind in light air in between getting blown around by fronts, but I finally made it. I tacked up the mighty East River in vacillating westerlies between 10-20 knots for three hours to make the current before it would become so strong behind me I would no longer have steerage. The wind died as I neared the junction between the East and Harlem rivers. The buildings took over. I furled the jib, turned on the electric motor and let the current do the rest. Despite the literal whirlpools, rapids and obscene amount of commercial traffic, I made it back out into the open water of New York Harbor by nightfall.

By now the motor’s batteries had been completely drained, and I was barely going 2 knots as I searched in vain for channel markers marking the entrance to Liberty State Park. Next thing I knew I had run aground on a half rock half mud shoal off Ellis Island. A few minutes later, though, the wake from a passing ferry rolled me off again, and I floated back into deep water, drifting the rest of the way into the anchorage with the last of the tide—and New York City finally astern. 

What I did right

• Had sufficient familiarity with my boat to know when I couldn’t outrun the weather systems offshore

• Sailed a strong boat with a full keel that can handle running aground

• Removed the external rudder from Teal’s self-steering wind vane before entering the East River, so it wouldn’t be damaged in the event of a grounding

What I did wrong

• Headed south way too late in the season

• Tried to sail back to Montauk Point a second time

• Didn’t anchor in the open-water anchorage off the Statue of Liberty and wait until daylight to navigate the rock-strewn channel

• Had old charts that showed nonexistent channel markers

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Photos by Emily Greenberg

Click here for part 2

April 2022