Haul hard! Cleat that halyard and watch the luff.”

Dad’s nautical commands were the soundtrack of my adolescence. But at 21, I wasn’t a kid anymore, and my mandatory crewing days on the Lightning were over. I had returned to the family cottage on Wellesley Island in upstate New York for Labor Day weekend and much-needed R&R from a demanding newspaper job in Manhattan. Dad had other plans for me, and on race day, I found myself back on board.

“Pay attention,” he ordered.

“I am.” But I wasn’t. I was waving to friends on shore when the Committee boat’s hand-held horn announced the midday start of the final race for Thousand Island Park’s Regatta Cup.

Chaos reigned as fifteen Lightning Class skippers jostled for position at the imaginary start line drawn in the St. Lawrence, a 750-mile river separating Canada and the U.S. I’d grown up here, as had my father and his father. Most summer residents had generations of feet planted on the island’s ice-carved rock. With Dad at the tiller, we were first over the line, but there’d be no pause for celebration.

“Watch the luff,” he instructed for the thousandth time in our years sailing together. I cranked my neck to study the topmost part of the jib for a hint of backwind.

Now in his mid-50s, he wore one hearing aid (an old injury) and a sunburn on his bald spot. But he remained a meticulous strategist and fierce competitor—not just in sailing but also as commander of a newspaper chain and master of his household of women—a wife and three daughters.

My sister Debby once joined Dad for what she thought would be a leisurely Saturday jaunt in the Lightning. Mom had packed Dad’s favorite lunch, peanut butter and onion sandwiches, and a six-pack of Dr Pepper. After a windless hour or two, Debby entertained herself by tossing random chunks of her sandwich to seagulls overhead. The birds snagged the repast in flybys.

“Stop it,” Dad said. “Those seagulls are blocking our wind!”

That ended their sails together.

As the youngest, at age 11, I was Dad’s last best hope. “Listen up,” he said. “Learn something.”

He taught me to treat every Sunday race like the America’s Cup of dinghies. Everything mattered: Set of the sail; distribution of weight; the capriciousness of wind. Over time, I discovered that other skippers didn’t share Dad’s bloodlust for winning. Their Lightnings contained coolers stocked with dark Canadian ale; their baseball hats turned backward for drinking. I knew this because I’d crewed on other Lightnings sporadically. No one was watching the luff. But I watched it no matter whose boat I was on. I’d spent too many years sailing with Dad.

On the second leg of this Labor Day race, Dad caught me trying to make a bowline with the jib sheet. “Wake up! We’re in a race.”

“Aye aye, Moby Dick,” I said. This drew chortles from Tim, the third member of our crew. Tim and I had been Dad’s Sunday lackeys throughout our preteen and teen years. Tim handled the mainsail and centerboard. (“Man’s work,” according to Dad). I worked the jib and Dad sat at the helm.

I loved Tim like a brother. Dad loved him like the son he wished he had. Tim had issues with his father; I, with mine.

As we rounded the third mark of the race, Tim raised the spinnaker for the downwind run. In the lull of this long, relatively inactive stretch, I opened a can of warm Dr Pepper I’d found rolling under the floorboards. We passed it around. Between sips and out of Dad’s hearing range, Tim said, “The Commodore,” as Dad was known locally, “taught me to keep my face to the wind while jockeying for position at the start line. That way, I’d always know my bearing relative to the wind.”

Dad had never told me that.

Tim drained the soda and crushed the can. “He also told me that when becalmed, I should light a cigarette to see which way the smoke drifts.”

I turned to give Dad a dirty look for favoring Tim with his nautical wisdom, but he was busy adjusting the mainsail another quarter inch. I looked back at Tim—shirtless, with longish, tangled hair. “So in all the years we crewed for Dad, I was the low-rent swabbie staring up at a patch of jib while you faced into the wind like Macho Man?”

“You’re as competitive as your father, you know. You’re just like him.”

“Stop talking,” said Dad. “Watch the curl.” The spinnaker’s lower left corner had curled inward. I trimmed the sheet until the sail filled again.

On approach to the last mark, the clambering resumed. Tim lowered the spinnaker, then he and I clawed it into the cockpit and stuffed it under the bow, all at warp speed. Dad did a wheelie around the buoy. Too close. I reached out to fend off.

“Touching the mark could be a penalty,” he said.

“Hitting it is definitely a penalty,” I said.

The last leg of the race included three long tacks. The wind picked up as the sun pulsed in the afternoon sky. The Lightning responded, heeling over in the steady blow. Tim and I scrambled to the windward gunwale to keep her upright. Timbers creaked, telltales flapped, and halyards slammed against the mast. As the Lightning bucked and rolled over the finish line, I looked over my shoulder at the other racers, too distant to be challengers.

Dad directed the choreography of our landing at the main dock. I eased the jib as we swept into the boat basin on a broad reach. Tim hopped on the bow, lines in hand, holding the forestay for balance. Dad pushed the tiller left, and the Lightning swung around at speed, heading straight for the dock. Seconds from impact, I let the jib fly, and Dad released the main, putting on the brakes. Twenty-one square yards of canvas snapped and flailed in the heavy wind, adding resonance to the drama. Momentum carried the boat another couple of feet, then stopped, inches short of collision.

Tim stepped on the dock and tied the bow, stern, and spring lines in perfect figure eights. Dad and I furled the sails. Then we watched the rest of the fleet cross the finish line in slow progression. Losers, I thought.  

This article was originally published in the November 2023 issue.