Boating and a big slice of humble pie

Many years ago, in the late ’90s, I had an old Star that I loved in a way that was inversely proportional to the aggravation it caused me. One of my top-five epic sails was aboard this boat, as was one of my top-five epic fails. The epic fail was with – who-else – my brother-in-law, Art, the one who was once pantsed when we flipped a JY-15 in a springtime regatta.

Allow me to set the scene: It’s a gorgeous fall afternoon on the Connecticut River, and the leaves ashore are a riot of red, orange and yellow. There’s a spanking norther, typical for the time of year, and the kind of light photographers love. In short, it’s a day capable of setting the sailing hook deep.

Art and I are putting the Star through its paces, tearing around the river like teenagers doing burnouts in someone’s dad’s sports car. We’ve just high-fived, and are making loud whooping noises, when suddenly both of us are thrown violently forward and the Star – her name was Shenandoah – has stopped dead in her tracks. Art and I exchange shocked glances. I look over the side. Holy smokes . . . is that . . . a pile of rocks?

Because we haven’t had time to de-power anything, we are now climbing – thanks to Shenandoah’s powerful main – up the side of the pile of rocks. The bow dips forward, meets resistance, and then the overwhelming horsepower of the main “hops” us up a few feet, where the boat levels off and the process begins anew.

We blow the mainsheet. What the heck? We’re on the western side of the river, in Old Saybrook, right near a popular marina entrance. We’re barely out of the channel. There’s nothing to mark what’s obviously a huge hazard to navigation.

Some blue language is loosed, mostly by me. We put our thinking caps on. The Star has a heavy, fixed keel to counterbalance her big sail plan, and most of the keel is now out of the water. It’s a dire situation. “We’ll kedge off,” I say, feeling smart, as I retrieve my new anchor and rode from beneath the foredeck.

Art reminds me of the following sequence at least once a year, usually at dinner parties. Standing on the foredeck, I heave the anchor with as much adrenaline-fueled strength as I can muster. According to Art’s well-worn narrative, the thing actually sparkles in the late-afternoon sun as it etches a silver-and-white parabola against the deep-blue sky. Both of us stand there, transfixed, as three-quarters of the way through its flight the anchor and rode part, and the rode flops impotently into the water. The anchor winks one last time, says, “Sayonara, boys,” and disappears, leaving behind a set of now-widening ripples.

Art and I look at each other. Suddenly all the fear and stress is gone. Just like that it’s been replaced by cathartic, can’t breath, red-in-the-face laughter. The hysterics last at least 10 minutes. “Oops. Guess I should have attached that anchor,” I finally manage.

We end up sailing off what I later confirmed to be an old Indian fishing pier; just sheet-in hard in a big puff and lay the boat over far enough to clunk, clunk sideways off the thing, no permanent damage done, but a lot of head-scratching and occasional fits of laughter on the way in.

I relate this tale as a way of making a point: Boating, more than any other pastime I can think of, except maybe occasionally golf, has a way of keeping you humble. It doesn’t matter how good or well prepared you are, you’re gonna have your moment, and probably in front of a bunch of people, too.

Recently I’ve been corresponding with a boat owner in Newport who was dismasted trying to sail 500 yards from his mooring to shore where he was planning on hauling the boat for the season. Several years ago a buddy, while leaving Block Island, with his wife and in-laws aboard, tore the bow out of his rigid-bottomed inflatable when he wrapped the painter around his prop. In this issue’s Last Word, frequent contributor Roger Long describes a trip years ago on a double-paddle canoe that rivals what Gilligan and the rest of the Minnow’s crew experienced in terms of original intent versus eventual outcome.

We all have trip-gone-wrong stories. In telling them, we both humanize ourselves and pass along valuable lessons. Do you have a New England-based story that’s 800 words or less? If so, send it to me at or to the snail-mail address listed in the magazine. If I get enough, I’ll turn them into a monthly column.

Remember: this is a judgment-free zone.

And everyone loves a good story.