THOUGH I GREW UP IN A SAILING COMMUNITY— CHARLESTON, SOUTH CAROLINA — I AM NOT A SAILOR. I wasn't allowed to sail because I'm not waterproof. I have no eardrum in my right ear. As a child, I imagined that if the boat capsized, my skull would fill with water and down I'd go, bow first. But when I was 41, I got a call from a childhood friend, Scott Wherry, who told me he was sailing in the biennial race from Charleston to Hamilton, Bermuda. They had an open berth.

There comes a time in every man's life when he must ask himself, "What can I endure? Of what mettle am I made?" This was not one of those times. I thought this would be a booze cruise to Bermuda.

So on a Sunday in late May 2005, I boarded the Tao, a 45-foot double-masted wishbone-rigged ketch (I don't know what a lot of those words mean), unsure how my life preserver worked, unclear on the difference between a sail and a sheet, the only knot I could tie a Windsor. We cast off, and the boat's owner, Paul Dorn, steered our eight-member crew into the harbor. Then rang the gun! Up came the wind! The sea called! Next stop, Bermuda!

Our mainsail started tearing immediately. It was new, had never been hoisted before, and was a poor fit. I got a quick lesson in making radial stitches on a 50-foot sail loaded with wind. Using a steel palm thimble and a pair of pliers, Eric Walker, a veteran sailor from Charleston, and I drove a six-inch needle through sailcloth stiff as rawhide. If you missed with the thimble, the needle would go through your hand. My pleasure cruise had quickly devolved into a Neolithic sewing circle. But the sail was saved, we passed Fort Sumter, and the land receded over the horizon and into memory. Ahead lay 777 nautical miles of ocean.

We divided into two watches, portside and starboard, taking turns manning the helm. For the next seven days, we would sleep, at most, four hours at a stretch—basically the same pattern Stalin used to break his enemies.

That first afternoon at sea, our power inverter blew out, meaning we couldn't charge our weather station, computers, or satellite phone. It also meant that none of us could jack our iPods into the stereo and crank up our carefully crafted nautical playlists. While this was a disappointment, it may have saved us from a lethal cocktail of Gordon Lightfoot, Christopher Cross, and Jimmy Buffett.

On day three, as we bobbed along in windless conditions, we lost both our toilets. Boat toilets, or "heads," are floating Porta-Potties. Ours, through an understandable oversight, had not been emptied since the Carter administration. We tried opening a relief valve (provocatively called an "ocean cock")—no go. It had to be pumped out by hand. As a father of three, I was used to dealing with other people's waste, so I volunteered, as did two other crewmembers. We took turns using a hand bilge pump to siphon the blue-water slurry into five-gallon paint buckets. After an hour or so, it was getting harder and harder to see out of my glasses. Turned out the gasket at the top of the pump had a poor seal; with every pump, a fine blue mist of aerosolized dook water sprayed into the confined cabin. I dropped the pump and scrambled topside for fresh air, my one great fear of this adventure suddenly vanished. I now knew that I would not drown. I would die from amoebic dysentery.

We gave up on the toilets, relying instead on the same five-gallon paint buckets, one of which was placed in the forward head. After each use, we lifted it gingerly and clambered abovedecks, shouting "Code Yellow!" or "Code Brown!" Not the most complex system, perhaps, but we were trying to convey an urgent message with utmost clarity.