Skip to main content

‘Shipwreck’ Sherwood and other mishaps

‘Shipwreck’ Sherwood and other mishaps

For almost 40 years I have written about sailing for various publications, stories that covered my boating-related mishaps and the experiences of others. Some events were not amusing at the time they unfolded, and one bordered near disaster and earned me the nickname “Shipwreck.”

Image placeholder title

But over time, in the retelling among boaters at social gatherings where such stories are often exchanged, they continue to draw much laughter, especially from those involved. However embarrassing they may be, they are never completely forgotten, although details can get murky over the years.

I don’t know why boating, especially sailing, provides such endless opportunities for mishaps, creating situations that can quickly go awry and turn embarrassing or even dangerous. I am reminded of a few explanatory lines from a book filled with things that went wrong aboard one particular sailing vessel before it eventually sank from sight:

“Oh, no, not again! When does it end?” asked a crewmember in distress.

“It never ends,” answered the boat owner and captain. “It’s a boat!”

Anyway, perhaps it’s time to record some of my own mortifying nautical misfortunes, so bear with me if you’ve read some of these accounts before. Let’s start with this “Shipwreck” business. Actually, there were two instances — sort of.

In the early 1970s I owned a Westphal One-Design racer — a 28-foot engineless keelboat with low freeboard, long overhangs, and a large, open cockpit that was not self-bailing. It was very wet going to windward in a chop, and it threatened to submerge at times. In fact, it is said that some “Westsinks,” as they’re known, sank so fast that their spinnakers may still be drawing in the currents at the bottom of the Chesapeake.

My unfortunate sinking came out of the blue in a freak 70-knot blow at the mouth of the Tred Avon River off Oxford, Md. My youngest son, Scott, and his buddy, both in their early teens, were on board for a daysail from Annapolis. I recall suddenly seeing a mainsail being shredded in the distance just before our mainsail was blown out in the process of dropping it. We were swamped by seas that quickly filled the cockpit, and we began going down in a hailstorm. We were strangely calm and stunned. We grabbed seat cushions and began climbing to the masthead as the boat disappeared beneath us. Luckily, the keel hit bottom, and the boat remained upright. I tied one cushion to the halyard to mark the hazard to navigation.

Fortunately, two couples in a large Swan spotted us and began circling. The Swan’s inflatable was strung out in a straight line and spinning like a top. Fearing the yacht might get tangled in my rigging, I shouted over the din to let the inflatable go and that I would swim for it. It went airborne, and I swam like a demon, finally grabbing a side line and flying toward the Choptank River Light.

I climbed in and tossed a bow line to the yacht, which was following me. We circled the boys several times before I felt it was safe for them to swim to me, one at a time, and I plucked them out of the cold water.

The second so-called shipwreck was aboard a friend’s 40-foot sailboat one chilly autumn night in a stiff breeze on the Magothy River. We had been at a party at the home of the late Fred Hansen when I suggested we go for a midnight sail. We were beating with the deck under when Hansen went below and found himself up to his waist in water. Clearly, it seemed we would sink unless we ran the boat aground, which we did. We had no radio, and I was nominated to swim ashore and call the Coasties, who arrived to pump the boat and tow us off. Several subsequent incidents occurred, including one where one of the crew was lighting flares and set his hair on fire. Technically, this was not a shipwreck, but that nickname stuck.

There’s another mishap I should mention regarding my son Scott. He was sitting on the boom, way out to starboard, as we ran downwind on the Severn River. When we went under the Severn River bridge, the wind shifted, and the boat unintentionally jibed, catapulting Scott off the port side. He clasped his hands and feet together in a diving position, and into the drink he went.

There's always the potential for a mishap of some sort when dealing with bridges.

I have flipped a dinghy a few times, once even at my dock, where I also fell off my boat once. I lost my sunglasses both of those times and once again when a wake from a powerboat knocked me off the foredeck while rigging a whisker pole for a downwind run. I also once rolled off my boat while sleeping in the cockpit.

Running aground accidentally in Chesapeake Bay is a given, but I had a habit of saying, “I know these waters well,” if a guest thought we were in danger of running out of water. Just as I said that during one sail, we immediately came to a stop. Bump! Then on to the drill: tie down the tiller, put the outboard into full forward, everyone to the bow, and start bouncing. I usually managed to get off without a friendly tow.

Cruising home to Annapolis one late-autumn evening, I tied up at a public mooring and dinghied to the far end of City Dock, where I tied up for a quick visit to a nearby party. I stayed much longer than expected, and during the interim the tide went out, and I was unable to climb down into the dink. So I jumped and immediately capsized. It was well after midnight, and I tried hauling myself out on a piling encrusted in sharp barnacles. I could not make it and began shouting for help.

Hearing my pleas, a fellow sailor came to my aid in his dinghy. Numb from the cold, I managed another capsize trying to climb into it, landing us both in the water. We swam to the nearest boat, towing his dinghy, and got hauled out by another overnighter. I retrieved my dink the next day, thanking the helpers I could find.

Cruising south on the Bay on the Upper Eastern Shore once, I decided to stop at Tolchester Marina for a late dinner. It had been a long day of sailing alone, and I was tired. After leaving the restaurant, I was motorsailing toward the distant lights of the Chesapeake Bay Bridge en route to Annapolis when I began dozing off and got disoriented. I looked up, saw the bridge lights, and headed for them. But the compass read due northwest instead of southwest, so I figured the compass must be off. After a few hours, I began checking channel buoys and realized I was looking at the wrong bridge, the Francis Scott Key span across the Patapsco River. It was time to find a place to anchor and get some sleep.

This article originally appeared in the March 2009 issue.