For my first day on the water, and the second race in the series, I was relegated to "rail meat," the quasi-affectionate term for crew members used as well-placed dead weight on the sides of the boat, allowing it to heel over just right for maximum speed. That day the sea splashed at my toes while the rest of the crew steered the boat toward the finish line. But just as we were about to cross, a massive 50-foot boat cut directly in front of us. We tacked quickly but bumped the committee boat—the official race boat marking the finish line. "I'm fuzzy on the whole good/bad thing," I said sarcastically to Chris D'Amore, another crew member. "Is it bad to hit the committee boat?" Cracking a beer, Chris, a perpetually grinning rugby player of a man, turned his back to the rest of the crew, stifled a laugh, and said, "Once everyone relaxes a little, this is going to be really funny."

With enough lobster, liquor, and palm trees, just about anything can be funny. That evening, we sat in the rocking cockpit of the Blue Loon drinking rum-and-Cokes, then powered our inflatable dinghy into Jolly Harbour. The sound of steel drums drifted from a gazebo off the main dock while hundreds of lit masts swayed in the harbor. Sailors hoisted slushy concoctions and hauled them from one outdoor bar to another, catching up and talking trash as they went. At about 11 p.m., we wandered into a full-blown outdoor barbecue with about 30 grills and makeshift bars huddled together. I went straight for the fresh Caribbean lobster—a clawless, sandy-colored, and more tender version of its Maine cousin.

For the next four days, I sailed and partied in harborside bars like Skullduggery and the Last Lemming, knocking back espresso martinis as I went. In between, there was "Lay Day" on Pigeon Beach, where sailors competed in tugs-of-war, sail-bag races (the nautical version of the potato-sack race), drinking relays, a coed beachwear swap, and, ahem, a wet-T-shirt contest.

Somehow we escaped a penalty on the second day, and by the fifth, the last official day of racing, we were in third place in our class but had not yet won a race. One boat, Justice, had edged us out every day, and although we were out of the running for an overall first-place finish, we had one last chance to stick it to them and snag some pride.

Boats zigzagged back and forth within feet of one another near the starting line, jockeying for prime position. Three boats to our starboard side were coming dangerously close to crossing the line before the starting gun fired. "Push them up!" yelled Chris. "Hold your course, Ralph!" That's when a crack! resonated as Justice was smacked by another boat. The gun went off, and we scooted right out in front of our competition. Sometimes one good maneuver—one lucky moment—is all you need. A couple of hours later, we crossed the finish line with over a minute to spare for our first and only win of the week, securing us a trophy for second place overall. Cheers went up, beers miraculously appeared, and my father, as even-keeled and controlled as they come, smiled broadly, his teeth so white he could have lit up a Christmas tree.

A few days later, the globe-trotting yachties were all saying goodbye to each other—and to the Caribbean. Some were crewing on private boats fanning out in different directions, and some would hook up in the Mediterranean or Newport, Rhode Island, where most of the big yachts were heading. Either way, the sailing and the partying would go on. My father was getting ready to sail back up to the British Virgin Islands to put his boat up for hurricane season.

After drinking champagne out of our trophy cup and making a pit stop at the swanked-out Lord Nelson's Ball, I capped off the week on the deck of the Blue Loon, sipping vanilla rum with my father and musing about nautical phrases, boat repairs, racing tactics, and whether or not he'd have to give all this up and go back to work. He thought he might have to—albeit reluctantly. "It's not a bad way to live," he said, almost mournfully, of race week, onboard living, and the vagabond sailing life. Dreading the moment when I'd have to put my socks back on and leave the life behind, I couldn't argue with him there.