You’ve got to know when to hold ‘em

Know when to fold ‘em

Know when to walk away

And know when to run

— Kenny Rodgers “The Gambler”

When I was young I would unflinchingly go out sailing in anything. Big boat, little boat, alone or with a crowd, it didn’t much matter. Same thing with setting all kinds of sail, weather forecast be damned. Reefing is for wimps!

This, of course, resulted in some memorable moments afloat, as well as some equally fun sailing stories back on shore. “Remember that one time when we set the kite and…”

Since then, however, I’ve become a good deal more cautious (or maybe “prudent” is the better word). Part of this, I believe, stems from my having had the opportunity to sail aboard a series of progressively larger boats, that and the fact that boats, in general, have become a good bit larger in general. It’s one thing to nearly capsize a 19ft Lightning while surfing in on some suddenly very large waves that have decided to start piling up just outside the harbor entrance. It’s another to nearly go overboard while wrestling with a flailing spinnaker in the dead of night aboard an overpowered 50-footer. The former gets the pulse racing, gives one pause for thought. The latter haunts my nightmares to this day.

I’ve also come to realize that an awful lot those same fun sailing stories I so enjoyed as a youth have a dark side as well. Never mind that in all too many cases alcohol was a factor. Even those that didn’t feature one too many drinks began to strike me as having been entirely unnecessary.

Granted, the nature of sailing, especially when going offshore, is such that the stuffing occasionally hits the fan. But the more I thought about it, the more it occurred to me that all too many of those same stories I most enjoyed listening to should have never occurred in the first place. Not only that, but in all too many cases they were, in fact, simply cases of bad seamanship, nothing more, nothing less.

Which is not to say doing the right thing is always easy.

Case in point: a couple of years ago I was part of a delivery crew preparing to take a brand-new Jeanneau Sun Odyssey 51 from a marina just south of Charleston, South Carolina, to the Miami Boat show. Now the Sun Odyssey 51 is an eminently seaworthy boat. However, in this case the boat was also brand-new, so much so that the company had barely even put in the mast, and the passage we were now contemplating would be her first time actually sailing. Worse yet, a frontal system was forecast to pass through, bringing with it big seas and even bigger winds out on the open Atlantic. What was a delivery crew to do?

Well, we hemmed and hawed and tried to figure out our best course of action. On the one hand, the wind was already whistling through the nearby treetops. On the other, being well up a lazy, Southern river, the water, though dark with catspaws, was flat as table. The wind, though forecast to top out at a moderate to fresh gale, was also fair.

In the end, we decided to delay our departure 24 hours, figuring we still had plenty of time to make our destination. This, of course, meant also having to find a way to pass 24 hours doing pretty much nothing in the middle of nowhere—an especially aggravating situation given that no sooner did we decide to hold off than the weather seemed to moderate, never mind what the National Weather Service said.

Fast forward to the next morning, though, and not only was the weather now icy cold, but one look at the seas left over from the night before was more than enough to make us all instantly glad we hadn’t been out them to see them come into existence.

Granted, in all likelihood, everything would have been fine—the same as when I’d helped out with another delivery from Charleston to Miami a few years earlier (a delivery so rough it soon had me puking up my guts the one and only time in all my life). But then again, what if the rig had failed? What if one of the innumerable bits of recently installed hardware come loose or become jammed? Sure, it might have made for a heck of a story. But then again, someone could have been badly hurt, and all because we’d been foolish.

More recently I was helping SAIL’s Cruising Editor Charles J. Doane bring his aluminum-hulled Boréal, Lunacy, back from Bermuda to her home waters in New England. It was just the two of us and some snotty weather with winds of 30 knots and more once again in the forecast—in the vicinity of the Gulf Stream no less. Still, we pressed on both having commitments to keep back home.

Then came the moment 24 hours later when we noticed a strange vibration coming from the rudder post. At the time we’d been motoring into a light headwind, occasionally backing down to remove a buildup of Sargasso weed from the rudder. This time, though, when we started motoring forward again, there was an undeniable rumbling emanating from somewhere underneath the cockpit sole.

Alas, when Charlie went over the side to see what was going on he not only discovered a small amount of play in the rudder post, but coming back aboard also noticed the telltale signs of ground-up bushing in the lazarette. Standing there in the gray dawn with Lunacy bobbing up and down on the gentle swells, we were temporarily at a total loss as to what to do.

Once again, though, we decided discretion was the better part of valor, which meant another, even longer 24 hours motoring back to Bermuda into what was now a headwind coming from the other direction, so that Charlie could pull the boat and see what was going on.

As fate would have it, the yard was booked and the prices exorbitant, so after checking with the builder to see what they thought had happened, we decided to head north again (the forecast having also now moderated substantially). However, this time we did so with a much better weather window and knowing exactly what it was we were facing.

As you may have already guessed, the 600-mile trip back to New England ended up coming off without a hitch. Save for a series of squalls our fourth morning out, the Gulf Stream was gentle as a lamb and by nursing the boat along, the rudder stayed where it should. Of course, there are those who might say our having such an uneventful passage meant we should never have turned back in the first place. But I couldn’t disagree more. Again, as far as I’m concerned, knowing when to turn around, to fold ‘em, so to speak, is as vital a piece of seamanship as any—all the more so because in our case, the forecast dirty weather reportedly ended up being just as bad as expected and then some. Who knows what might have happened should the Gulf Stream have decided to show us its truly ugly side?

Bottom line: I have zero regrets with regard to our decision, and I don’t think Charlie does either. Now that, in my mind is a good sea story! 

Photos by Adam Cort

November 2019