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For as long as I can recall, boats have been my waking dream. The syncopated rhythm of the sea and the great passages it promised soothed my anxious soul, this product of a shattered home. For me, the ocean was all hope and potential. It was a universe unto itself—and one I understood more intuitively than what I navigated on the less forgiving landlocked terrain.
We lived a block from the harbor—among the most idyllic on the East Coast—but our reality was many miles away. My parents divorced when I was two. It was the opening salvo in a blind, bitter battle of wills between two radicalized warriors who lacked the presence of mind to recognize the collateral damage they inflicted. Their warfare persisted for decades and my older brother and I were wounded in the crossfire.
Saltwater was my salvation. When the drama at home reached its crescendo, I’d escape out the back door and walk a block to the Cliff Street boatyard where I’d climb down a shaky ladder appended to a mossy seawall and drop down to a long, narrow, floating dock used by riggers and boat wrights to step the masts of classic sloops, yawls, and schooners owned by families unlike my own.
I’d find an old cushion or life preserver and make a nest. This ritual became like sensory therapy. The rolling surge of the tide, the smell of organic decay, menhaden, alewife, and other baitfish gutted by blues, stripers, and various predators higher on the food chain, leaving oily slicks on the water’s surface; the faraway cry of a gull (“rats with wings,” we’d say); the mournful groan of a foghorn wishing sailors a safe passage. For me, the ocean was womblike in its embrace. It was as familiar as my own hand. Saltwater, I would later say, coursed through my veins.
I was a shipless—somewhat shiftless—mariner. I wore water-soaked deck shoes that squeaked nauseatingly to the rhythmic cadence of my limp gait, and my elbows and knees were perpetually tattooed with barnacle scabs, the telltale marks of the wharf rat.
We lived in the Shipyard District, which meant that, while we were favorably proximate to this lovely harbor, we were on its working side. It wasn’t exactly the other side of the tracks, but it was a long way from the Eastern and Corinthian Yacht Clubs out on “The Neck,” the peninsula forming the eastern boundary of the harbor, which featured all of the trappings of Gatsby-style prosperity, old-line Waspy tradition and white-bread privilege—a place that greeted sunsets with the military tradition of colors, flags raised to synchronized time in lockstep with ceremonial cannon fire. It was a place where clothing, diction, and lineage were all served up in the starchiest of whites.
Despite my obvious love for the sea, my relationship with boats began tenuously. After my parents divorced, my mother lived with a troubled man with an equally abiding affection for the ocean. Toby came from a wealthy, socially important and emotionally repressed family who refused to acknowledge the undiagnosed learning disabilities that would be his eventual undoing. Sailing was his first escape; here, he was able to represent his family with dignity, the steely-eyed resolve expected of Benjamin men. Less productively, drug abuse was his second escape. As he entered our lives, the latter was overtaking the former; his Ted Turner outlaw persona had mutated from charmingly dangerous to a much more disturbing variant of the same.
Toby’s reputation as a half-crazed Olympic-class sailor made him something of a local celebrity. The truth, of course, was less romantic: he was an unemployed drug abuser living off the fumes of a diminished trust fund. By most standards, he was “a bum,” but his charm and talents belied this simpler characterization. He was still invited into privileged circles, like the scion of society he was in name alone.
Each summer, beginning in my early youth, my brother and I piled into the cramped jump seat of my mother’s Alfa Romeo Spider convertible to make the two-hour drive to the Kennedy compound in Hyannisport where we’d sail Victura, a Wianno Senior gaff-rigged classic wooden sloop originally owned and raced by the thirty-fifth U.S. president. Toby was the hired gun sailor commissioned by this famous clan to captain Victura in weekend regattas.
While Toby and my mother raced around the buoys on Nantucket Sound, my brother and I lounged with Ted, Teddy, Patrick, Kara, and a throng of minor celebrities and non-celebrity hangers-on on a fancy spectator boat dressed in nautical flags and other cheerful yachting regalia. Senator Kennedy sat big-bellied and shirtless in the center cockpit, making no efforts to hide his various indulgences, which were well documented in those days. He arrogantly held court, as if anyone needed to be reminded who was the imperial captain on this particular ship.
Even for an eight-year-old, it was a heady experience. But despite my grand initiation into sailing, I was by no means hooked by what I saw as a slow, subtle, and generally dull way to spend an afternoon. I associated it with assholes and blowhards, which in retrospect was a fair characterization for what I would eventually conclude was the eternal blight of this otherwise perfect sport. It would take many more years for the rhythm of the sea to get under my skin—but when it did, it became like a song I couldn’t get out of my head.
Once the depths of Toby’s addictions became clear, my mother asked him to leave. I recall feeling something like pride for what was indeed a rare example of maternal instinct. My mother loved us deeply, that was absolutely never in doubt, but she was hardly a paragon of domestic order and responsibility. As a parent, her instincts could be questionable.
I had nothing but searing contempt for Toby, but somehow his absence left a void. In that empty space was now a yearning for the sea. I knew I would need my own boat.
The fact that I didn’t have two nickels to rub together probably should have been of greater consequence. I was an optimist by inclination and a dreamer by necessity, and I was rarely weighed down by inconvenient details—like facts—when they didn’t suit my narrative.
I had become a discriminating admirer of boats. I’d swoon at a graceful sheer line, a slender, overhanging stern, or a full, flared beam. I admired a dark hull for the way it reflected against the water’s surface and felt that fiberglass lacked the soul of wood. I had opinions on the practical and aesthetic tradeoffs between a yawl and a ketch (both have a mizzenmast aft of the helm, but the latter has a much larger, more functional rig that adds substantial square footage to a sail plan). The shape of a boat was my first encounter with what can only be described as lust.
As an armchair yachtsman, I had become an aesthete of the highest order, an otherwise unrefined kid from a broken home with nothing short of cultivated, middle-aged opinions when it came to what a proper boat ought to look like. I’d look down my nose at cloying cigarette boats and crass fiberglass cruisers shaped like bulbous Clorox bottles. I fancied myself a little William F. Buckley and even managed to convince my mother to buy me my own three-piece suit, which I wore proudly with scuffed sneakers and a crooked bow tie.
I was, by all accounts, a strange kid.
Lust is certainly what I felt when I first saw her. I was first boat struck by an eight-foot plywood catboat with a gaff-rigged mainsail cut from the inky red sailcloth you’d expect to see on an ancient Chinese Junk plying the waters of the Yangtze River, not this New England harbor. It was an eccentric little craft, which suited me just fine. She looked like the better half of an upturned walnut shell polished and shellacked like a piece of furniture. She was, to my eye, perfection.
After school, I’d dump my books and find a perch on the cliffs high above the foot of the harbor where I knew this boat was moored. She belonged to a boy about my age whose parents owned a tidy shake-shingled house on a private point with its own dock not more than a block or two from my own house—but, needless to say, many worlds apart. That wasn’t my source of envy. My envy was for nothing more or less than this little nutshell sailing pram.
Despite the often tenuous circumstances at home, my mother and I had an uncommon closeness.
We were both slightly off center—different—with a similar appreciation for quiet, aesthetically rich moments. Perhaps more important, we were both dreamers, rarely allowing our fraught circumstances to undermine the natural optimism we shared. We’d take long walks through the crooked streets of our beloved town, pointing out small vignettes of variegated rooftops and brightly colored shingles, layered to form the perfectly composed peek at a shimmering harbor. We’d point out sailboats, conspiring how one day we’d have our own. We’d plot a different future, dreaming aloud and wholly believing that these dreams we generated were actual plans in the making—blueprints for better days—not the hallucinations they would prove to be.
My mother helped me buy my first boat. It wasn’t the nutshell, which I’d since realized was either something you built from a plan, which was no small undertaking, or bought secondhand for several thousand dollars, no smaller undertaking still. Instead, I settled for an eight-foot fiberglass dinghy, a more common, less beautiful version of the nutshell. My mother helped me scrape together the three hundred dollars, a substantial sum for a ten-year-old. My father, who was mostly absent at the time, surprised me with a new outboard motor, which I hung proudly on the footboard of my twin bed for the remainder of that impossibly long winter.
I launched my first boat too early the next season, beginning my tradition of rushing into a boating season that wasn’t quite ready to begin. It was a windy day in early May, the harbor a bare gray canvas against a forlorn sky. I named my boat Bottoms Up, for no other reason than having once seen a vessel I admired with these letters blazed across her transom. I hadn’t the foggiest notion what it meant and, by the time I recognized it as the drinkers’ refrain, it was already affixed proudly to two sides of the hull in large block letters. I spent two seasons unintentionally advertising what surely suggested an early taste for alcohol.
Every few years I found the means to upgrade my boat and, because my mother had the foresight to put my name on the waiting list with the harbormaster upon first seeing the glint in my eye, I had my own mooring at the tender age of twelve. I recall a twinge of satisfaction when middle-aged men would lament angrily about the ten-year waiting list to secure their own spot.
Because we couldn’t afford a yacht club or launch service, Bottoms Up served as my tender. I’d row against the tide, barely making good into a stiff headwind that exhausted my bony arms. The tide always slackened, the water’s surface black and flat, as I turned the corner into my protected cove. Here, my boat sat high on her lines, bow faithful to a faint breath of wind. I’d own that moment by taking my time to complete these final strokes.
Someone once told me that you could tell a lot about a sailor by how long it took him to row ashore. The truly boat struck take their time. They savor a graceful sheer, a slender, overhanging stern, how the water reflects against the surface of her hull. The truly boat struck are overtaken by nothing short of lust when they admire a fine vessel sitting proudly at her mooring.
I was certainly boat struck, then and now. For it’s a lifelong addiction, a condition the afflicted aren’t soon to shake.