ODDLY, HER CURSE WORKED more like a blessing. Our first swim—a two-and-a-half-mile warm-up from the Virgin Gorda ferry landing, in Spanish Town, north to the Little Dix Bay resort—went, well, swimmingly. Our "safety" boat—a 25-foot motorboat captained by photographer Paolo Marchesi and first-mated by his assistant, Derik Olson—didn't turn up. (In fact, they wouldn't appear until later that night, complaining loudly about their SS Minnow–quality tub.) Given my nascent shark hysteria, this could've been a bad thing. As we began our first leg, I was doing my best Don Knotts imitation—head and neck bobbing all over the place looking for fins—but the scariest thing we passed was some razor-sharp coral just a foot below the surface, with hundreds of Finding Nemo fish darting in and out.

The surfboard was surprisingly easy to handle. Hopper had devised a simple tethering system: a strap buckled around the waist, attached to a 12-foot length of polypropylene rope. Weighing ten pounds and loaded with about 40 pounds of our things stuffed in two drybags, the board definitely slowed the puller down, reducing speed by about a quarter, but even so, we managed to reach Little Dix Bay in just under an hour. We emerged from the water Sean Connery style, peeling our goggles off in one fluid movement as we strode through the soft Caribbean sand.

"Nice swim," Hopper said.

A woman lounging in a black bikini looked up and asked, "Where did you two come from?"

"The ferry landing," Hopper answered nonchalantly, unstrapping his drybag.

"Oh," she said. "But that's a few miles away, isn't it?"

"Yes," Hopper answered. "It is."

"Wow, that's so cool."

A waitress walked by and we ordered Red Stripes and ceviche. "Name?" she asked, rather sweetly.

"Carter . . ." I answered. "Hodding Carter."

Despite rustling palms, tropical sun, and fawning girls in bikinis, spring break was turning out to be a little different from what I'd imagined. Instead of passing out naked on coed-strewn beaches, Hopper and I shared a one-room cottage that blended nicely into the local vegetation. Our dates for the evening were Paolo and Derik, a long-footed Italian and a skinny, redheaded Montanan, respectively, and I definitely was not making out with either of them. So we did the next best thing and drank as much of the house rum as we could.

Later, lying in his sumptuous king-size bed, wrapped in a white bathrobe, rum drink in hand, Hopper said, unexpectedly, "I feel a lot more confident about our swim. I feel like we're not gonna die."

"That's good," I said and passed out on the cot next to him.