As 25 Daysailer boats veered toward the final turn of my first – and what would be my last race at Stage Harbor Yacht Club in Chatham, Massachusetts. – I felt the spray of salt water splash on both my face and forearms as I instructed my hearty crew of two to literally “stay the course.“

For some still inexplicable reason, I had been appointed as skipper on a modest Daysailer on the last race of the summer season for the “12 and unders.” Not only did I not deserve the honor, but it was also actually dangerous to put me anywhere near a boat except as a handler of the jib as part of a well-seasoned crew. But my brother, Mark, just two years older at the time, was a forbearing and discerning sailor, so “the powers that be” surmised that I had the same DNA. In retrospect, however, if my brother was Jimmy Carter, then I was his younger brother, Billy.

While Mark took to the sport like butter on toast, I was baffled by the anachronistic lexicon, the sketchy edicts, and upper-crust mores that defined sailing. As a foreshadow of what was to come, Mark, a future headmaster, was a confident patrician, while I was a down-and-out plebeian. Half the time, I literally didn’t know what to do, so I just winged it to whoever was in my boat, using my enduring wit as a deflective measure. “Okay, guys, ready about – ‘hardly’.” Everyone would then guffaw and shake their heads at the jokester guiding the boat.

After our sailing lessons, my dutiful sibling would come home discussing the significance of studying the sea pattern to windward as a way to tack correctly. I would then comment that the Stage Harbor Yacht Club had purchased two dozen “Daysailers” from the boat’s renowned designer, George O’Day, “at a good price,” according to the Program Director, David Hovey. 

“It must have been a good sale!” I remarked to my mother.

“Oh, Shaunie!” she laughed, probably wondering how she could “spawn” two such distinctly different boys 19 months apart.

As usual, Mummie had the best of intentions when she signed her two youngest children up for sailing lessons. Of course, she had learned to be a proficient sailor at the same club three decades previously, and as someone whose ancestors had lived and died in Chatham at the elbow of Cape Cod, our mother yearned for us to at least have a semblance of ability in such an enhancing life skill. “Boys, it’s in your blood,” she would say as she drove us down Route 28 from our cottage in Eastham.

Situated on the northeast shore of Nantucket Sound, Stage Harbor, a semi-colon-shaped body of water, was flanked by hilly terrain dotted with stunning summer houses with red-rose-covered white picket fences, which gave it an otherworldly feel.

One month and some 40 hours of lessons later (including a wealth of experience sailing in the intimate Chatham harbor), my brother and I traipsed down to the dock for the big race of the season on the last day of the summer season. When Mark was assigned to lead a boat of three, I was not at all surprised. After all, he was competent, if not really good, at everything he did, and this was his tangible reward for a job well done.

However, when I observed that I had been assigned as skipper to two twin boys a year younger than me, I thought that it must have been a misprint. I almost flew up to the Stage Harbor Manager, the affable Dave Hovey, to inform them that they were making a giant miscalculation. In the end, however, I kept my mouth shut, thinking… maybe they know something I don’t?

When the horn sounded to begin the race, at least 20 or more Daysailers crossed the starting line, and we were all off. My modest crew consisted of two identical twins named Harry and Pete, who were two years younger and just as inexperienced as I was. Despite my ebullience, they seemed edgy as we skidded out into the deep-blue waters of Stage Harbor. The water was placid that morning, and there was a hint of wind blowing from the southwest. All three of us squinted our eyes as we headed north toward the first main buoy where we would turnabout.

In Secretariat-like fashion, our little wooden sailboat unfathomably sprinted out in front and led all other boats as we approached the buoy, which would signal that a port tact was in the offering. “Hey, guys, we’re in the lead!” I bellowed. The boys in the boat didn’t know whether to laugh or to cry; you could smell their fear as clearly as the shifting Nantucket Sound tide. For me, it was a “roll down the window and let the wind blow back your hair” kind of moment, and for a brief interlude, I felt as if we were on top of the world.

As my crew and I approached the initial buoy, I reminded my charges that we would see a turnabout soon. At the time, the twins seemed up to the challenge. Timing is everything in life, however, and as we approach the red-and-white-painted marker, the wind, which has pushed us to the lead, stopped as suddenly as a cab at a school crossing. It was as if all of the air in our balloon was instantaneously released.

Out of sheer momentum, we passed the marker and began to drift towards the north along with the current, which seemed invigorated that it was taking three passengers with it. I looked back and observed every other boat successfully tact to port and continue on the racecourse.

“If only we had a motor attached to this craft!” I shouted to my crewmates. They didn’t seem amused and began to panic as our Daysailor continued to dawdle far away from the rest of the boats. I looked ahead and saw that we were methodically heading towards far-flung Morris Island.

“Ah, guys, we might off to push off from there!” I exclaimed to Harry and Pete.

Instead of agreeing with me, they both burst into a harbor of tears (pun intended) and began crying out for their mother.

Oh, boy. Or perhaps I should say, oh, boys.

Later on, my mother explained to me that we had hit “the irons,” and that that was “not a good thing.” I learned that a sailing craft is said to be “in irons” if it is stopped with its sails unable to generate power in the no-go zone. If the craft tacks too slowly or otherwise lose forward motion while heading into the wind, the craft will coast to a stop. In my case, I simply looked for a “coast” – meaning Morris Island – to stop the boat.

Unfortunately, I let my humor and my prevailing sense of optimism get the best of me at that moment. “There we are, guys! An island to land on! Get ready to ditch this boat for safe land!”

You would have thought that I had asked them to give up candy. Their subsequent cries could be heard all the way to Nantucket.

A few minutes later, after moving the Daysailer to dry land, I convinced the twins to start walking the secluded beach of Morris Island in search of help. I knew that we would have to be there a while until high tide began to come back and help us cast off the little peninsula. Both kids continued to bellow; Harry continually called out for his mother as if he were about to walk down death row to be electrocuted by Old Sparky. Eventually, we did run into one old sprite Chathamite who said, with typical salty New England humor, “Well, gentlemen, this is not a bad place to spend the winter.”

I chortled immediately, but my comrades were now bereft, thinking that they had ultimately landed in an unrelenting gulag.

In the meantime, the boats back in Stage Harbor had all come into port safe and sound, and my brother, Mark, and his craft – of course – had finished among the top handful of boats. After the last Daysailer arrived, Mummie began looking for me, thinking that I had somehow scurried by her and toward our car, which would then take us to the local beach.

On the dock, a plainly distraught woman, you got it, Harry and Peter’s mother, was frantically looking out in the ocean for any sign of a boat with three boys in it. She accosted David Hovey, who recounted the boats and bellowed, “They’re all here!” He didn’t know that an extra Daysailor had been added to the usual fleet that day for the race. There was still one more boat out there – and it was safely ensconced on Morris Island.

Over the next hour, both mothers searched everywhere for their lost ones, but my mother typically was much cooler and casual about the entire affair. “Oh, Shaunie will show up somewhere, and there will be a funny story attached to it,” she exclaimed to her longtime friend, Betty Kennedy, who had also begun to look for me.

To make a long story short, Mummie, whose confident demeanor intimidated most everyone she came across, convinced Dave Hovey to “give the harbor another glance” with his high-powered range binoculars.

By this time, Harry and Pete’s mother wanted to the Coast Guard, but Mr. Hovey, another practical Cape Codder, would have none of it. “Well, I’ll be damned,” he declared, “I see three specks; they must be boys, walking in single file on the beach of Morris Island! And there is a boat out there – stuck in the irons.”

Within half an hour, Dave Hovey had motored to us, attached the Daysailer to the stern of his Boston Whaler, and shot us home, a streaking arrow of white zooming across the blue waters of Stage Harbor.

As we alighted from the boat, Harry and Pete sprinted towards their mother on the dock and enveloped her as if they had been at war in the South Pacific for three years. The trio heaved spasms of tears that flooded the dock like a prodigious nor’easter.

In contrast, I took my sweet Jesus time and profusely shook Mr. Hovey’s hand as I embarked from the Daysailor, which seemed to sigh in relief as it was tied to the mooring. I then observed Mummie standing adroitly in the modest parking lot adjacent to the dock. With her hands resting assuredly on her hips, she was clear-eyed, chuckling to herself, and obviously amused that her baby had gotten himself into another kerfuffle entirely of his own making.

I skated past the overwrought rendezvous of Harry, Pete, and Mama on the dock, and climbed up the ladder to the parking lot with a cheery, bemused expression on my face.

As I neared my mother, I gleefully bellowed, “Well, Mum, you can’t win ‘em all!”

Her wheezed cackle could be heard all the way to Orleans.