From Flickr user Mr. TinDC https://flic.kr/p/as6kyS

Let’s Go For It

The rocky New England shore belied itself to British mariners crossing the Atlantic. The stone is almost entirely granite, not marble. Despite this error, settlers seeking relief from the moral celibacy of Puritan Salem made their way to the neighboring peninsula and named their new port Marblehead.

Like most coastal Massachusetts towns, Marbleheaders sought their destiny on the ocean. Building an economy on the burden of the abundant North Atlantic, Marblehead grew into a maritime juggernaut, capitalizing on fishing and trade. During the Revolution, the seafaring talent was turned from merchant activity to military; Marblehead was the birthplace of the United States Navy.

Time passes and industries collapse. A tremendous gale in 1846 nearly destroyed the fishing fleet, and the town never quite recovered. Commercial fishing was mostly ceded to other yachting communities on the East Coast, but the sailing tradition couldn’t be suppressed. Inextricably linked to the heritage of the (uncannily quaint) small town, the allure of the wind and the waves could never be torn from the town’s identity.

Generation upon generation of men were groomed from childhood to be comfortable on the sea, as the focus turned from sailing as a livelihood to sailing as a competitive pursuit. The second oldest yacht club in America, the Boston Yacht Club, sits on the edge of the deepwater harbor, as do three other clubs with equally prolific histories. The Corinthian, named in honor of the genteel spirit of the sport, the Eastern, home to three of the earliest America’s Cup victories, and the Pleon, from the Greek for sailing, the oldest junior yacht club in the country. Marblehead certainly earned the title “Yachting Capital of the World.”


It’s at Pleon, the club started by a group of young men to compete with the more established clubs, that most current Marbleheaders are taught the art of sailing and seamanship. It’s at Pleon where my mother dragged me the summer after second grade, through fits of tears and complaints that sailing is stupid, and my proclamations that I knew how to do it anyways. You just pull the rope to go faster.

Her roommate in college had a son, Alex, the same age as me, and being proper Marbleheaders, it was expected that we’d at least give sailing a shot. It was Alex’s mother who signed us up, damning me to what would surely be a miserable time that would be better spent romping about in the woods or watching cartoons. Yet, the prospect of hanging out on a dock with my friends seemed like a pretty good alternative, and I eventually obliged.

The swim test, a harrowing twenty-five yard sprint through the dark, briny water to a mooring coated in barnacles and seaweed, nearly dissuaded me from returning after the first day. I hated it. Hated the water, the ocean, the muck, the fish, the prospect that any number of malicious, imaginary sea-beasts lurked just beneath my dangling, skinny pale legs. But I went back the next day, and the day after, and every summer day after until I no longer belonged at a junior yacht club.

I suppose now that the swim test has much less to do with gauging swimming ability and much more to do with forcing young children to face their fears. I’m eternally grateful to Alex’s mother for placing me in the Pleon program, because sailing bestowed upon me some of the most transformative experiences of my life.


We came about to starboard tack, the hull violently pitched over me as Fred whipped the jib across to leeward and we both leapt to the rail to flatten the boat. A deep baritone blast from the committee boat signaled one minute left in the starting sequence. I shoved the tiller back and forth, sending the bow erratically left and right, as water splashed over the gunwale and cascaded around the vee-shaped break to prevent the boat from swamping. A Nor’ Easter loomed offshore, lumbering its way up the coast towards Halifax, and the ten foot swells rendered the little wedge pathetically ineffective. Staying dry was not an option.

There were fifty-nine other 420s on the line, all more or less identical to ours. This is one-design dinghy racing. Sailing is a technical sport, but one-design racing is meant to eliminate any yacht design advantages. When all of the boats are the same, the only differentiating factor is the sailor.

“Thirty seconds!”

Fred eased the jib sheet to a full luff — the wind flowed across the sail, flapping in the wind like a flag rather than deflecting it to create lift on the centerboard and hull, which would send the boat forward. I eased the main sail, decelerating the boat as we continued to jockey for a clear starting position amid the cacophony of the line. I released the vang to open up the top of the sail, countering the momentum-damping waves and the howling breeze.

“Up, up, up, you fucker, head up!”

“No room! You have no fucking room!”

Remember, Marbleheaders left Salem to avoid the strict Puritanical ways. Sailors aren’t known to be particularly polite in the first place, and especially not on a crowded starting line.

“Twenty seconds!”

Safe from any late-comers trying to push us over the imaginary line drawn between a flag on the committee boat and a bright green inflatable tetrahedron, I took a moment to consider my strategy for the upwind leg. Being across that line when the gun sounded would result in a penalty that would all but eliminate any chance of a favorable finish. The sea state seemed to amplify itself as seconds ticked away until the starting gun. It was hard to tell from our position at the favored pin end, but the line sagged at the middle as the rest of the fleet struggled to confront the endless swells. Had I been more poetic in the moment, I might have recalled the melancholic last line of Gatsby: “So we beat on, boats against the current, borne back ceaselessly into the past.”

“Ten!”

“Trim, trim, trim! Get ready to roll!”

Roll wasn’t a metaphor. At the start of a dinghy race, the crews will dip the boat to the leeward side, and immediately after leap to the windward side as they snap the sails in tight, dramatically increasing the opposing force of wind on the sail and water on the foils, one of the few ways to legally accelerate the boat.

“Five, four, three, two, go!”

The brass cannon on the bow of the Pegasus, the race committee boat hailing from the Corinthian Yacht Club, erupted across the water. Rather than listening for the sound, which can be difficult to hear above the luffing sails, whipping lines, and humming shrouds, the crew watches for the muzzle flash to call the all-clear.

Miraculously enough, the race committee didn’t toss the X flag nor the first substitute pennant. Not a single boat in the fleet was over early. The increasingly rough conditions and resultant line sag probably had a hand in that.

We managed a clear start in the top tenth of the fleet, pumping the sail to power through each crest and trough. It was impossible to sail a close angle to the wind without swamping the boat, and the first beat was a rough, slow slog, despite the wind speed inching towards the twenty knot mark.

After about three-quarters of a mile with minimal movement in the fleet, we prepared to round the top mark and bear off; the wind now coming over the rear quarter of the boat. Fred climbed forward to attach the spinnaker pole and release the halyard, and as soon as he was ready — three, maybe five seconds — I stood in the middle of the boat and hoisted the bright, colorful foresail hand over hand, in three great heaves.

A kite set, as it’s known, can be one of the most dangerous maneuvers in a 420. The boat picks up speed instantly and becomes extremely unstable while skipper and crew move their weight about the hull to set the sail. It’s second only to the gybe, a move that involves the sails violently crossing sides of the boat and the crew having to duck the boom while throwing the spinnaker pole like a javelin across the front of the mast.


This was the last race on the last day of Marblehead Junior Race Week, the annual regatta that draws hundreds of junior sailors from around the world to compete in one of the premier events in the United States each summer. Open only to sailors age eighteen and under, this would be the last year that Fred and I sailed a 420 together. One last hurrah, and by the last day, we had a shot at a respectable finish, if not a medal.

We had sailed together since seventh grade, going through Pleon’s racing program together, stuck on a small fourteen foot long boat together, all summer long, for many long summers. It had been a tenuous test of friendship; I’m hardly the most pleasant person when my hand is gripping a tiller, but despite many shouting matches and emotional episodes, the camaraderie that developed between skipper and crew prevailed.

This wouldn’t be the last race we sailed together, but it would be the last race in the 420 I had bought my sophomore year of high school with money from a job working at a boating supply store in downtown Marblehead. The boat had been our baby, and we had meticulously cared for the hull, the spars, and the sails. After the regatta, a family from Connecticut would put it on a trailer to give their daughter who was just beginning her foray into sailboat racing.

Seven years of sailing together meant that we were perfectly in tune with what the other was thinking, and could anticipate each other’s moves. It’s very valuable, as a skipper, to have a crew with that level of understanding. Instead of counting down to a move, Fred would see the same things I saw, and nothing more than a silent nudge was necessary to spring into action.


The downwind leg was thrilling. The wind had steadied at around eighteen knots, and the ten foot swells were coming in a predictable rhythm behind us. Being older than much of the fleet, we were able to leverage our size to keep the boat flat, and bring the hull up on plane to surf with the waves, passing others who didn’t intuit the longer wavelengths and were sucked into the troughs.

We approached the second to last mark, another inflatable tetrahedron, where our angle to the wind would change and force us to gybe. Most of the other boats had taken the conservative route, deciding not to launch their spinnakers at the top mark. Those boats were well behind us; the extra sail area was a calculated risk, but it gave us an enormous advantage.

A group of boats formed a block in front of us as we came ever closer to the gybe mark. Every boat had to leave the mark to their port side, and there are strict rules about trying to force yourself in between the mark and another boat. As the overtaking vessel, it is your responsibility to steer clear. Fred and I faced a crucial decision: play it safe and round outside of the six or seven boats ahead of us, and try and pass them on the next leg, or pass them all in one swift maneuver by gybing early and shooting the gap between the lead boat and the mark.

This is the type of decision that can’t be left unspoken, but we were on the same page. Fred is the best crew I’ve ever sailed with; I had no doubt he could get the spinnaker across before we had to cut inside. We went for it.

I stood in the center of the boat, and grabbed the spinnaker sheets like the reins of an agitated mustang. With the tiller between my knees keeping the hull perfectly parallel to the wind direction, Fred gently tugged at the vang, and the boom violently swung 180 degrees across the boat at his slight provocation. The jib already having switched to the starboard side, Fred reached up to reset the spinnaker pole on the port side of the mast.

At the most inopportune moment, a swell lifted the boat, sending the top of the mast high into the air, where the uninterrupted breeze is much stronger. The spinnaker halyard, the line holding the sail to the top of the mast, is held in place by a small jam cleat with tiny, carbon fiber reinforced teeth. Under the increased pressure of the gybe and drenched conditions, the tiny teeth slipped, sending the spinnaker high above the mast like a child’s kite. In a matter of a second, the halyard snarled and stopped the sail from releasing all the way.

In the middle of a gybe, on top of a swell, the powerful sail tore the mast forwards and down, the boat capsizing to windward. Sailors call this a death roll.

I was thrown a few yards from the boat, which sat listlessly on its side, taking on water and slowly turning upside-down, the bottom of the hull bobbing above the water like a turtle shell. Fred had been caught by the vang and dragged underneath the water, trapped out-of-sight amid the carnage that had been the finely-tuned rigging of our boat just moment earlier.


The fear I had felt as a nine year old swimming in the harbor was entirely irrational. There were no mythical creatures waiting to pull me beneath the depths, and the water was relatively warm, despite my shivering.

It had been years since I experienced true fear on the water. I’d been through my fair share of hairy situations, but they were rarely dangerous, just mistakes that would lead to poor finishes. Proper training and experience transforms sailors from feeling timid trepidation at the thought of windy days, to rip-roaring adrenaline junkies, begging for that next heavy air day.

But maybe we had pushed ourselves too far. Maybe we should have rounded the mark outside, well clear of those boats. We had the weight advantage; we could have passed them on the last leg. None of that had passed through my mind when making the decision to gybe and cut inside; there was a complete absence of childlike apprehension.


I swam furiously towards the boat, terror sinking in, waves tossing me about and making the distance between myself and the boat seem interminable. Had it not been for the maddening stress of staying above water and striving to reach my boat and the animalistic survival instinct that had kicked in, the guilt of having put my crew, my friend, in significant jeopardy might have been immobilizing.

The glee I felt upon seeing Fred floating on the other side of the boat, clinging to the mast to keep the boat from turtling completely, was one of the greatest rushes of relief I’ve ever felt. I couldn’t decide if I should laugh or cry, but it was definitely enough to make me forget that my rigging was a wreck of aluminum and dacron, shredded by the ocean the way the Marblehead fishing fleet of antiquity had been shredded. The spinnaker had torn apart at the top, the pole bent, and the wire of the port shroud was frayed to the point of breaking.

We managed to right the boat, cutting the spinnaker free and untangling the rigging enough to limp back to the yacht club. We’d later find all sorts of other minor damage.

Perhaps it was an appropriate end to our junior sailing career. We had pushed our limits; wasn’t that why we loved sailboat racing in the first place? For the rush of adrenaline, the challenge of crossing our own boundaries? Sailing has always been about man against the sea, taming nature and forcing it to bend to our will. Fred and I had assessed the risk, applied our knowledge, and made a split decision — the wrong one, it turns out — but we didn’t hesitate to act. This time, we had exhausted our luck, gone to the absolute brink, and came out unscathed.

The visceral sensation of riding on the very edge of control, teetering on the brink of disaster, testing my will and my ability, is what makes sailing fearful and ultimately, fun. Just like the fear of the ocean didn’t stop me from returning to Pleon on my very first day, I won’t let fear stymy my enthusiasm for sailing. The thought of retiring, even taking more than a few hours off, was absurd then and is now. Maybe, instead of the curtain closing on my youth sailing career, that day in late July was the end of my youth.