When the unthinkable happens, a young sailor has to figure out how to cope with the consequences.

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It’s 11 in the morning, and we’re about 15 nautical miles off the coast of northern New Jersey when I sit bolt upright from my nap on the starboard settee to find water rolling across the floorboards. I shriek to Nic in the cockpit and slosh over to the engine compartment to see the poor diesel half-submerged but still dutifully chugging away, the flywheel flinging seawater like a lawn sprinkler. There must be hundreds of gallons in here!

My newly minted fiancé and I were taking my 30-foot steel sailboat, Little Wing, from Virginia to Connecticut, needing to get the boat north to our new home before winter. We’d plodded up Chesapeake Bay and down the Delaware, stopping in Cape May before an overnight to New York City – mostly uneventful until this surprise flood.

We quickly realized the running engine was exacerbating the flooding and shut it down. Nic rigged up our mobile backup pump, alligator clips attached to a battery that was unstrapped and ready to be lifted to higher ground if necessary. I steered us in the vague direction of Sandy Hook. The pump was keeping pace with the water ingress, but with only a knot of boat speed over the windless ocean, we wouldn’t make it to shore until the next day. We called the U.S. Coast Guard for help, and they connected us to the Fire Department of New York. Their Marine Patrol 8 appeared on the horizon a few hours later to whisk us into New York Harbor at a hull-rattling 15 knots, fast enough to suck most of the water out of the boat like a self-bailer.

By the time we arrived at the only marina in the area that could haul us out that same day, the sun was near setting, we’d been managing a flooding boat for more than eight hours and still weren’t sure exactly where the water was coming from. The armada of technicians who awaited us in the lift well were a welcome sight.

Little Wing emerged from the Hudson River, and I finally exhaled as brown water drained out of her stern like a sieve. A tech handed us two cleaned-out yogurt containers of neat bourbon. It didn’t take long to see what our problem had been: The entire steel compartment below the propeller shaft was a rusty mess with daylight pouring through. This dark, narrow, inaccessible compartment must have been corroding, thinning, and ready to breach for a while, and had decided to cave in on this particular October day.

A Fork In The Road

Nic and I had hoped to have our upcoming wedding somewhere on the water, somewhere with a dock where a fully-dressed Little Wing would be on display. For the next six months, we doggedly pursued repairs and solutions.

Right away, we thoroughly cleaned the salt-encrusted engine and doused it in WD-40 to prevent rust, and swiftly performed every manner of cleaning, pickling, and preserving on the other systems. We cut the mangled compartment off, and a metal fabricator friend made us a new one. Just before we enlisted a welder to attach the new compartment, we bought an ultrasonic tester to check the metal thickness of other areas of the hull. The results were devastating.

The closer we looked, the more we found. Battery cables crunched when bent; salt had percolated inside. More rust blossoms appeared where interior paint exposed to salt and oils was starting to peel. It didn’t take long for corrosion and mold to spring up everywhere like persistent weeds. Before long, everything about the boat looked like a giant question mark. We were overwhelmed by the snowball effect.

We couldn’t sell her and pawn our problems off on someone else – that didn’t sit right with me. It might have been easier if Little Wing had met a sudden and catastrophic end, sunk on that fateful day, and we could have been grateful to have walked away with our lives. But that’s not what happened. Over many late nights, we brainstormed and calculated, factoring the staggering repair costs and the mending that would be required for me to trust her again. The cold, hard, logical answer couldn’t be ignored.

Pulling The Plug

Researching how best to scrap my boat felt like researching how to dismember and dispose of a body. How do I surgically remove each piece of the whole to preserve organs for future use? How do I pluck out the engine, her heart, so I can sell it for transplant into someone else’s vessel? What about winches and blocks, her muscles and joints? Who would take her empty shell? Will she be crushed, melted down, reformed, little pieces of her steel body reappearing as soup cans on grocery store shelves?

These nightmares kept me awake for months. I’d restored Little Wing with my dad’s help over a full-time year of work, giving her a second chance at life after 20 years neglected on the hard. I’d scoured every square inch, installed every system that I now pondered how to uninstall. My blood, sweat, and tears were permanently integrated into her hull, memorialized between metal and paint. Together, she and I put thousands of miles under her keel. She led me to Nic and inspired me to pursue a career writing about boats. Steel boat owner. Writer. Captain. Wife. All things I might not be today without this sweet old boat.

Once the decision was made to scrap, there was no turning back. We started with the engine. A chainfall was strapped to the boom on one end and attached to the engine’s lifting point on the other. I worked the chainfall from the cockpit while Nic corralled the slowly rising engine from inside the cabin. It didn’t fit through the companionway.

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The corroded compartment in the stern was nearly impossible to see underway, but the daylight pouring through was glaringly ­obvious after the haulout.

“How in the world did you get this in here in the first place?” Nic asked through gritted teeth as he pulled back on the dangling engine so it wouldn’t hit the wall. I stared at it. “Oh, I remember! We have to take the feet off.” Nic continued pulling back on the engine for several minutes while I used a socket to quickly remove the feet. He released, and the engine swung out of the hatch.

We contracted the yard to unstep the mast and remove the hazardous, still-half-full fuel tank. Nic and I pulled the batteries, windlass, air conditioner, electronics, saloon table, lines, winches, blocks, and pretty much everything else. As we removed organs bit by bit, undoing all the work of my year-long restoration in less than half that time, each piece conjured memories, like sifting through a shoebox of old photographs. I remembered wrestling that hose into place, shimmying behind the engine to tighten that bolt, cutting that hole to run that wire. I wondered, at what point is she no longer a boat. Was it when I finally unscrewed the designer’s plate from the bulkhead and stuffed it into my pocket?

Little Wing emptied out and our basement filled up. We hoped to recoup something from this mess – perhaps sell some parts or install some on a future boat.

An Empty Hunk Of Steel

I had the bright idea of turning Little Wing into an artificial reef. Being steel, she was technically eligible. A final resting place among antique New York City subway cars, providing habitat for fish and opportunities for divers, didn’t sound half bad. After some back-and-forth with the New York State Department of Environmental Conservation, a representative from its artificial reef team came out to inspect the boat and determined that the cost-benefit analysis didn’t make sense on their end. He suggested that we could prep the boat to the long list of state standards ourselves, weld a patch over the hole with welding skills we did not possess, tow her offshore to a designated site using a powerboat we did not have, and sink her. The state could provide the permit.

“Sink her?” I asked. “How?”

“Well, you can open a seacock and run, or you could use explosives,” he said. This seemed beyond our capabilities.

I called some metal recyclers. The steel hull and lead keel had to be worth something. Scrapyards, as it turns out, are unsympathetic to any emotional attachments one might have to a hunk of metal. They could bring in an excavator, crush it, and take it away in a wide-load truck for about $5,000. I winced.

I asked the boatyard for their disposal quote. “So, we’d have to get plasma cutters, and OSHA training, and a special dumpster, and … .” Cutting to the chase: “Around $13,000.” I lost it. We’d already removed everything! Eventually we agreed on $3,000 and handed over the title.

A Healthy Dose Of Caution

Brokers were unprepared for the kinds of questions I asked during our yearlong search for a new boat. One gorgeous sloop sported an inaccessible propeller shaft compartment that looked eerily similar to the one that ended Little Wing. We didn’t buy that boat. We found red safety flags on every one of the dozens of boats we examined, or the boats were out of our price range.

Finally, we found Fernweh. At 25 years old and 47 feet long, she’s half Little Wing’s age and offers significantly more living and storage space for the trips we hope to take. She’s fiberglass, not steel, so secret rust is unlikely to be a fatal flaw, although my corrosion paranoia will probably be lifelong. I insisted upon spending the first night after Fernweh’s spring launch aboard, listening intently to the water lapping against the hull, compulsively opening compartments to ensure none of it had weaseled inside. So far, Fernweh has been much less porous than Little Wing ever was, which I appreciate deeply, and I’m beginning to trust her integrity.

This past fall, Nic and I sailed Fernweh from Rhode Island to Maryland, a route very similar to Little Wing’s final trip, but in reverse. Amid the hullabaloo of prepping and provisioning, I hadn’t really thought too much about that fact, nor that I hadn’t been out of sight of land since that fateful day. It hit me on the second night, when an unusual yellow glow eased onto the horizon: the glimmer of lights from distant New York City. Somewhere over there sat what was left of Little Wing. As if she was suddenly jealous watching us glide by on a new boat, the wind filled to 30 knots and Fernweh laid down onto her rail.

One day heavy machinery will crush Little Wing’s hull and deposit it into a dumpster. I won’t know which day. I don’t think I’ll ever be able to drive by that yard to check.

As far as I’m aware, newspapers don’t accept obituaries for inanimate objects, although I’d argue Little Wing had quite an eventful life. In light of that, I’ll leave this quiet epitaph here for her instead:

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Kelsey sailed Little Wing thousands of miles between the Chesapeake and Florida after an extensive refit during the pandemic.

EPITAPH

Little Wing: 1974–2025

Built in Friesland, a province of the Netherlands abutting the North Sea, Little Wing sailed thousands of challenging ocean miles. Under the stewardship of her final owner, she was saved from her abandonment in the Maryland field where she’d languished for two decades and restored at the hands of a college student with a cruising dream. Together they sailed thousands of miles more. Little Wing braved many muddy groundings, less-than-perfect dockings, and questionable repairs, but she always delivered her young crew safely back to shore, even on her final day. She leaves behind a sailor who now has memories of incalculable value, a life trajectory immeasurably altered, and an acute fear of rust and inaccessible compartments.

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Published: December 2025

Author

Kelsey Bonham Bailey

BoatU.S. Magazine Associate Editor

Following a childhood filled with varnish and Chesapeake Bay brine, at 20 Kelsey refit her own sailboat top to bottom, then skippered the 30-footer down the ICW. She’s been an instructor on boats up to 100 feet, has won several awards from Boating Writers International, judged the NMMA Innovation Awards, and holds her 25-ton Master’s license. Kelsey brings her on-water and environmental experience to the magazine’s news, personality, lifestyle, and product coverage. She and her husband sail a Jeanneau Sun Odyssey 45.2 in New England.