Voice of Experience: Going Wrong in Fives

John D. Macdonald, through his iconic character Travis McGee, observed that one thing never goes wrong on a boat. Instead, things go wrong in threes.
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John D. Macdonald, through his iconic character Travis McGee, observed that one thing never goes wrong on a boat. Instead, things go wrong in threes.

 Illustration by Michael Penick

Illustration by Michael Penick

A spring delivery turns into an endurance test

John D. Macdonald, through his iconic character Travis McGee, observed that one thing never goes wrong on a boat. Instead, things go wrong in threes. Well, on one spring migration from the Virgin Islands to New England aboard our Hylas 45.5, Egraine, things went wrong in fives.

We left St. Thomas in what I wouldn’t exactly call a window: it was more like a gun slit. In a place where the wind always blows from the east, it had been coming from the west for days. Hurricane Adrian had formed in the Pacific and was forecast—correctly, as it turned out—to cross Central America and reinvent herself as an Atlantic cyclone, or at least a dangerous storm. Our weather guesser, the esteemed Dane Clark of Jenifer Clark’s Gulfstream, explained that our April weather looked more like October, with lows blowing off the coast every three days. It was an unprecedented pattern.

Unfortunately, my crew, TJ, and his dad (who had sailed with me before), were restless, and we were running out of time, having scheduled two weeks for a trip that typically takes nine days when things go well. So when we saw something close to a normal barometer, with clear air and a wind blowing from some version of east, it looked good enough. We couldn’t contact Dane, but decided to go anyway—although I did advise some less well-equipped skippers who were keying on us that they should not follow our lead.

When we finally did reach Dane, he said we had made an “interesting decision,” not the most rousing endorsement. He added that we had positioned ourselves between two anomalous troughs, both moving north-northeast, about 50 miles apart. If we overran the one in front or got overrun by the one behind, we should expect to experience some truly extreme weather. Oh, and we should expect the wind to blow mostly from the north.

Sure enough, we spent the next three or four days beating northward, motorsailing most of the time, trying to stay between the troughs, which revealed themselves at night as spectacular light shows, one in front and one behind. In keeping with Dane’s advice, we also tried to stay west in the hope the remnants of Adrian would pass ahead of us.

Finally, on day four it looked like we might catch a break. The troughs seemed to be dissipating and the wind shifted to the southwest, until we found ourselves on an exhilarating broad reach in 35 knots of wind, making 8.5 knots over the ground. The sea state was comfortable, albeit building, driven by the strong breeze. This is what Egraine was made for.

That’s when the genoa halyard parted, dumping $8,000 worth of 3DL headsail into the drink. Luckily, the helmsman was sharp and the crew quick, and we ran off and recovered the sail. However, with its loss, fate finally caught up with us.

The first sign of trouble came just after midnight in the form of a series of blinding lightning strikes so close we could not tell if they were hitting the boat. Not only did they leave us night blind, but a 60-knot gust blew my glasses off my face and overboard, “blinding” me for the duration. Afterward, our youngest crewmember, who’d thoughtfully pre-positioned the rigging cutters close to the companionway, did his best to keep me up to date with a series of damage reports. Clearly, we had run smack into what was left of the tropical storm. 

In fact, the convection was so severe that even 200 miles southwest of Bermuda I was chilled to the bone. The wind direction was also indecipherable, which caused us to eventually broach on the face of a towering breaking wave. As the mast went horizontal, the harnessed-in crew—now standing on the cockpit coaming—blew the sheets and made sure they ran free. Egraine skidded sideways on the face of that wave, came more or less upright, and then stuck enough of her rudder back into the water to let me point her downhill. We were riding a 30,000-pound cruising boat like a surfboard. Twenty miles east of us, we later learned, a catamaran turned turtle, killing her crew of three.

At this point, in addition to having lost our big headsail, we were short of fuel after days of beating. We were also short of time and still had 850 miles to go to Newport. Two-thirds of the crew, my mate and I, were busy lawyers who needed to get back to work. Bermuda beckoned to us from “only” 240 miles away. Making 8-plus knots as we were, that was little more than a day’s sail away. 

Without consulting Dane—which we could easily have done—I turned the boat toward Bermuda and straight into the path of what was left of Adrian, which by then was reported to be only a strong squall. Riding with two reefs in the main and the tiny staysail, we were making 8-plus knots in winds that had increased to a steady 40 knots with seas that were building to 10-12 feet.

That afternoon we got a huge radar return 20 miles out, which we then tracked, sight unseen, as it sailed on a reciprocal course. Normally in daylight you can see almost as far as radar. The fact that we couldn’t make out what proved to be a supertanker until she was six miles away should have told me we had lots of moist energy-laden air.

When we finally saw her, the tanker’s bow was throwing up so much spray it was engulfing her superstructure a few football fields away. As I stood on one foot, leaning against the shrouds, talking to the tanker driver on my handheld, he asked if we needed assistance. I scoffed. Later that night, it occurred to me that maybe I should not have been so cavalier.

The storm came on in classic style, with torrential rain and enough wind to shake the world. We got through it, however, thanks to a fine crew that never hesitated to do what needed doing. A lot of stuff got thrown around below, and although I’m not sure why, a couple of stanchions were bent. I also got mighty cold and will never again go on watch, even in the Caribbean, without a foul-weather jacket. Eventually, though, we got to Bermuda, made repairs, flew home and lived to fight another day. 

Despite the hardships, there were also some funny moments. At one point as TJ was providing damage reports from the companionway while his father and I wrestled with the helm and mainsheet during our broach, I asked him to hold off for a while. “What did he say?” he asked. His father replied: “TJ, he said shut up.”

Another time, there was an acrid smell and a crackling sound in the center cockpit, which sits atop the engine room, causing me to think we were on fire; with all the lightning it seemed a distinct possibility. When TJ turned a light, though, to see what was going on, what we found was a large flying fish flopping around the cockpit. 

The following morning from my bunk I heard my first mate say to TJ, “You have to be nice to the skipper today. He saved our lives last night.” I laughed aloud, all too aware of the fact that it had actually been my bad decisions that almost got us killed.

“Guys, I only saved my life,” I told them. “You just happened to be there. And by the way, if I could have left and gone home, I would have.”



Twice I made decisions based on our schedules, without due deference to the unusual conditions.

I didn’t call Dane to get an informed perspective on our turn toward Bermuda.

I let the disappointment of bailing out for Bermuda dull my senses and, because we were riding well, ignored the intensity of the conditions.

I did not appreciate how intense even a fading tropical storm can be, especially when layered on top of charged conditions.

I should have had a strap to hold my glasses on and a foul-weather jacket to keep me warm.


We had a strong boat designed to survive conditions like those we encountered.

We discussed in advance what to do in case of a knockdown.

Everyone had harnesses that can be released under strain, which they used to stay tethered to the boat.

The crew reacted flawlessly after the knockdown to make the necessary adjustments to keep the boat moving and on her feet.

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