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The Prodigal, 500 miles south of Nova Scotia

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s a few friends will recall and the few readers of scattered press reports at the time have surely forgotten, I was sailing alone, ten days out of Charleston, when I made the decision to abandon a leaking, weather-beaten, fifty-year-old ketch named Prodigal in rough seas about 500 miles south of Nova Scotia. The month was June, in the year 2015. I was one-third of the way to Ireland on a 3,500-mile passage I had planned for months. The implosion of my second marriage had come just three weeks before. I had set sail anyway, already mired in one storm, headed inevitably for others.

As was the case with most of the boats I have acquired through the years, I had bought Prodigal for a pittance and fitted her out for a king’s ransom. I sailed her for a week up the Chesapeake Bay from Norfolk in 2013 and solo for seventeen days nonstop on a shakedown cruise to Bermuda and back in June 2014. Mechanical wind vane self-steering gear—the indefatigable but dear Monitor brand—freed me from all steering responsibilities offshore and allowed me to get snatches of sleep at night. The split ketch rig made for steady sailing in rough weather with the mainsail furled and the mizzen and foresail (the smaller sails at each end of the boat) flying.

Prodigal had leaked a bit on the 2014 voyage to Bermuda, but no more than could be easily mopped up with a few swipes of a sponge from the cabin sole. She was an old boat, but I am an old man, and we hardly begrudged each other a few imperfections. The passage to Ireland was different. After a glorious week of good weather, Prodigal took quite a pounding in heavy conditions and began leaking more than before. The United States Coast Guard (not at my invitation but of their own volition or someone else’s), was following my progress with uncharacteristic interest, as I discovered when their New York group began communicating with me by satellite text messages. They expressed concern short of alarm at my terse report to Facebook friends, at the time, that I was “taking on water.” (I concealed my concern approaching alarm that the government had the time, interest and ability to peruse my Facebook posts.)

The Coast Guard offered a rescue. I politely declined and stoically assured them I would be fine, not realizing at the time that my automatic, electric bilge pump, throbbing away deep in the bowels of the ship and unheard above the fracas of wind and wave, was pumping out water not quite as fast as it came in and steadily draining my battery, giving me a false sense of security as to the rate and volume of the leak.

Why draining the battery, you ask? Because on a sailboat and most especially a sailboat built in the sixties, the motor is the source of electricity, and the motor itself is more of an ornament than a main source of power. This owes to the fact that there is only a very small space in the slender, lovely yacht designs of the sixties into which to squeeze a motor at all, and an even smaller space in which to squeeze a fuel tank. Motors on sailboats are called “auxiliaries” for this reason, because to depend on them primarily much less desperately for anything (including generating electricity to charge batteries and run bilge pumps) is folly. It’s rather like depending on your 110-pound girlfriend to beat up the loud-mouthed guy in the bar, or depending on the baloney sandwich in your lunchbox to save you from starvation. Both are there, yes, and both will function after a fashion, but not very well or long. Relying on an electric bilge pump at sea to continuously evacuate an ongoing leak, and on the boat’s  motor to keep the pump charged, far from fuel docks and diesel supplies, is never a long-term solution—and being 1000 miles out into the Atlantic in a 30-foot boat, carried inexorably northward by the Gulf Stream, is the very definition of long-term.

Prodigal, an Allied Seawind Ketch built in 1965 in the Catskills of Upstate New York, was a tender sort of yacht—tender being a term that refers to the propensity of some boats to tilt over quickly and far when a breeze hits their sails. In Prodigal, this characteristic stemmed from a design that combined a narrow beam with a shoal draft, “shoal” meaning shallow and “draft” meaning the depth to which the keel extends below the water. Boats with narrow beams and tall masts need long, heavy keels filled with lead to counteract the force of the wind on the sails above the water. That’s because the more the wind blows a boat over sideways, the higher she lifts her keel, and the heavier and longer the keel, the more force gravity exerts on it to return the boat to level. Once a boat gets underway, the energy of the sails and the keel acting at cross purposes is expelled preferably in forward motion, not continued sideways motion to the point of capsizing. It is the envied characteristic of a deep-keeled boat that the wind can blow her over only so far until the force of the wind upon the sails can lift her keel no higher, at which point the boat stops absorbing all that wind energy by heeling sideways and converts it to forward motion instead, boring through the waves like a bus. Here endeth the lesson of keels and wind and the mysterious motion of boats.

But deep keels are problematic for the majority of American sailors who never sail in the deep, blue waters of the sea and instead spend their weekends skimming over shallow, muddy estuaries like Chesapeake Bay and Pamlico Sound. And so Prodigal’s designers, like those of many other American boats, saw fit to give her a lightweight keel that extended only a brief four-feet and some inches underneath her thirty feet of length overall. As a result, she was ruled more by her sails than her keel, making her a bit “tippy.” With all sails flying she often sailed “on her ear,” as sailors say—with her leeward rail (the side that dips low when a boat heels, opposite the direction of the wind) awash or underwater. And because, like most old boats and old people, she didn’t fit together quite as sleekly as when she was new, when she sailed in this fashion Prodigal leaked at her seams. A widening gap of open space in the connection between her decks and her hull—the two solid, molded forms of fiberglass by which she was constructed—siphoned seawater into the hull, especially during periods of high wind and seas, when the rails were awash.

On the passage to Ireland, a second storm late at night caught me by surprise. I was flying too much sail when it hit. Ideally a sailor sees a storm coming and reduces sail-area ahead of time to give the wind a smaller target and steady the motion of the boat. Not this time. This was just before the advent of GPS devices that now deliver inexpensive, accurate satellite weather forecasts to sailors in remote parts of any ocean. I was relying on friends sitting at their computers at home to text me the weather forecast for my location. A buddy in Washington State who fancied himself something of a weather guru had sent me the happy and mistaken news, that night, that I could sleep well in gentle, fifteen-knot breezes. I should have trusted my instincts to the contrary. Near midnight, the sea became as smooth as glass, and there wasn’t even enough wind to hold a heading. This was the proverbial calm before the storm. Sudden changes in wind speed almost always signal a weather system that is reorganizing itself for a dramatic change in direction and strength. So it was that night.

Once the front hit, everything in my world was suddenly tight, sideways, drenching wet, pitch black, and plunging up and down like a demon. I was flying the large, full mainsail (the one in the middle) and the working jib (the one in the front)—not the mizzen (the one in the back). I might have dropped the main and raised the mizzen to “split” the sail plan and steady the boat, but the conditions were just short enough of worrisome to give me pause before doing so. In strong winds and pitching seas, standing on the cabin top to release a large mainsail, then trying to get it all down, folded, tied and sorted, is like trying to rope a wild, frightened steer. The operation comes with its own set of risks that have to be balanced against the risk of doing nothing. The violent motion of a small boat getting bucked in the waves and the difficulty of keeping your feet underneath you, in the dark, on heaving, wet and slippery decks without hitting your head or breaking a limb, threaten to take the problem of a merely uncomfortable angle of heel and turn it into something exponentially worse. With no one to man the helm but a mechanical wind vane that needs sails and forward motion to work, there is the added problem, once the mainsail is struck or slacked and the boat looses steerageway, of keeping the boat headed into the waves and not turning sideways into a trough in the waves, where it can toss about and broach violently while you attempt to raise the next sail and get the steering back on track. I have done all of this before, many times, and too often not elegantly or well. It resembles a bull ride with the risk of getting thrown somewhere from whence you cannot simply pick yourself up and dust yourself off.

I knew it would be an uncomfortable night—in fact I slept lying mostly sideways against the inside of the hull that night in the forward berth—but I also knew the boat was never in danger of capsizing. I have sailed in many storms, and their bark is almost always worse than their bite. This was a blustery frontal system, not an organized major storm. I had supreme and well-founded confidence that Prodigal would shoulder the load and weather the conditions even with her mainsail fully unfurled, and she did.

But what I saw on the morning light gave me greater pause. With only manual pumping every few hours to stem the inflow of water, the rate and volume of water entering the boat through the hull to deck seam had increased dramatically. My feet touched down from the forward sleeping berth onto the cabin floor that morning into water sloshing over my ankles that covered the entire cabin and was rising into the forward bow section. The wind and seas were in no more or less foul a mood, but suddenly I was rapidly losing confidence in my vessel and the wisdom of the voyage. A few minutes of nervous bailing seemed to make no difference. Indeed, the water seemed to be rising slowly, and the boat by this time no longer had her rail in the water to explain where a continued flow of water might be coming from. I looked for a seacock (a hole in the boat controlled with a valve that opens and shuts) that might have accidentally failed but found none.

The idea of another three weeks and 2,000 miles headed to Ireland in a boat leaking this badly filled me with dread. I quickly dispatched a short message to family and friends on Facebook that I was taking on water more precipitously and looking for a cause. It was at this moment that the Coast Guard contacted me again and offered—urged might be the better word—a rescue from a nearby ship, the State of Maine, a training vessel of the Maine Maritime Academy.

I made a decision at this point that I would roll over in my mind for months to come. The better decision at such moments is always an emotional one, not a financial one. Too many sailors have gone to their doom chasing dollars into the abyss. I have been something of a minimalist since my first fevered readings of Thoreau and the Gospels, aided by the fact that I have made enough money from the comfortable ramparts of a law practice to be neither greatly impressed with what money can do nor greatly worried about my ability to get more of it. I never lived in terror of losing things or despair to hang onto them. The real wealth and fortune in life is time and freedom, which makes the free man in forma pauperis the wealthiest and most fortunate person in any room. I was always much more impressed by people who made the most out of their time and wasted the least of it than those who made the most of their wealth and spent the majority of it. The really poor bastards, it always seemed to me, were the ones who traded their years of health and vigor for the diminishing returns of business or profession or career that were destined finally to vanish without a trace in the memory of the world. In the end we have each other and such of our integrity as we have been able to preserve, and that is all.

On the sea that day, I had an estranged wife beckoning me to return to work on my marriage, and while I had been willing to defer that work to achieve the lofty aim, once begun, of sailing alone to Ireland, suddenly the idea of risking life and limb to go bailing my weary way into some God-forsaken shipyard in frozen Newfoundland, all so that after paying handsome storage fees for two or three or five years’ time I might find a cod fisherman gullible enough to take Prodigal off my hands for a few farthings, seemed far less noble. This makes no sense, I know, to the man who will walk two miles past one shop to save three cents on a foot of pipe at the next, but I have never wanted to be that man. He is welcome to his bargain. I am content with mine.

Which is why I took the offer, stepped off of my leaking boat, and said goodbye. The crew of the 248-foot ship State of Maine, manned by some hundreds of eager, fresh-faced midshipmen and their instructors on passage from Spain, executed their first-ever rescue at sea that day. Three days later, TV crews and newspaper reporters greeted me at the docks in Portland, eager to record the story that England’s Daily Mail cheekily called “stranger than fiction,” about an American novelist who had lost his yacht but saved his marriage.

It was a lovely story while it lasted, which is to say through three weeks of local TV news interviews and an AP story picked up around the world, but in the end I would lose boat and marriage, stem to stern, the hull and the rigging, the having and the holding—all gone. Susan asked for a divorce; I relented, and I left.

I suddenly had no ship and seemingly no purpose. Having recently sold my practice and retired from the law to make way for the obscure life of an unsung novelist, I also had no clients and no job. My children were grown, educated, and sorted in their own careers and faraway cities and relationships. For the first time in my life I had nothing to do and nowhere to go. So I sold everything I owned and took the first plane to nowhere.

This is the first chapter of a coming book to include the Voyage of Nevermore.