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IT'S A LOT HARDER THAN YOU MIGHT THINK to swim from island to island across four-knot currents, gargling salt water hour after hour, getting chased by sharks, and towing your worldly possessions on a five-foot surfboard while flying the British flag. (It's even harder when you're told on your very first day in the British Virgin Islands that your British naval flag is actually a Swiss flag.) What with the jellyfish, hecklers, and excessive rum intake, you might even think twice about swimming your way through the Caribbean.

W. Hodding Carter

Making the haul from Virgin Gorda to Ginger Island.

W. Hodding Carter

The author and Hopper practicing good anti-shark stroke mechanics in the deep water between Peter and Norman islands.

W. Hodding Carter

The SwimTrek BVI! boys off Virgin Gorda.

Virgin Gorda

Virgin Gorda

But that's what I did for spring break.

Why, at age 43, couldn't I have just plunked myself down at some swanky resort? Blame it on my midlife-crisis swimming fixation, in which I've bragged quite publicly that I'm going to make it to the 2008 Olympics in the 200 freestyle, even though I never even qualified for the trials in my prime. In fact, I pretty much sucked as a younger swimmer until my senior year at Kenyon College, when I came sort of close to qualifying—finishing two seconds behind in the 200 free (akin to being five minutes back in a marathon). After that, I went on with my life, albeit with the nagging thought that if I'd just had a little more time, I could've made it to the podium.

Now, at the last possible moment, I want to see if I was right.

When I first resubmerged myself in the swimming world last fall, I was like any other midlife dingbat pedaling past you in traffic jams or burning rubber at the local treadmill. I was swimming six days a week. Pumping iron. Counting heartbeats. Getting in touch with my inner guppy. But something was missing: I wasn't having any fun. And I wasn't going all that fast. So I decided to train more like I had in college. That meant downing plenty of fresh-squeezed lime margaritas, doing vodka shots in the Jacuzzi, and spending money like my daddy would bail me out. My wife and four children weren't amused, but, sure enough, I got faster. Soon I was closing in on my old pace.

As my besotted winter blurred by, I figured I'd head south like all the other kids for spring break, only instead of passing out on the same beach every night, I'd swim from island to island. That way I could keep up my Olympic training, with only a few tweaks to my rigorous schedule: swim, eat, nap, drink, nap, drink, eat, drink, sleep, repeat.

PREPARATIONS WERE SIMPLE. I chose the British Virgin Islands because they looked close to one another on a Web site's cartoon map. The southeast trade winds dictated a southwesterly route: Virgin Gorda, Ginger, Cooper, Peter, and Norman. Ginger Island was uninhabited, so I'd have to camp, but the rest was resort splendor all the way. Twenty miles of fun-filled Caribbean waters, if you could put out of your mind what the St. John–based kayak guide told me:

“Oh. Ginger, huh?” Arawak Expeditions owner Arthur Jones said when he heard my plan. “I don't know—it's pretty sharky. I remember hearing about someone else who tried that off St. John a while back, and she had to stop halfway through because of a shark. It just started following her and getting closer and closer. But I don't know. Maybe that was just a rumor.”

Suddenly thinking about that old bear joke—the one about not having to outrun the bear, just the guy next to you—I invited my friend Hopper (a.k.a. George McDonough), a 35-year-old landscape architect I'd met at the Y, to come along. A former Division I swimmer at the University of Rhode Island, he was about three months behind me as far as getting back in shape was concerned—in other words, a little bit slower.

“Sure,” he answered. “Where?”

Hopper actually proved useful as more than just shark fodder. We wanted to be self-sufficient and tow everything we needed. I had the bright idea of using a kid's blow-up raft; Hopper had the even brighter idea of a surfboard: low-profile, able to hold a lot of weight, and with tail fins to keep it in line. Hopper was seeming more and more like a good choice. Not only did he come up with a name for our adventure—SwimTrek BVI!—but he also turned out to be an experienced open-water swimmer, having raced at distances up to eight miles. It was Hopper who suggested we bring duct tape and epoxy for board repair, a VHF radio, a Swiss Army knife, a chart, a couple of pairs of Crocs, and the flag we'd fly above our board to warn away boaters. I came up with resortwear and toothbrushes. In my defense, I also got some racing wetsuits that would protect us from Linuche unguiculata, the stinging, itching thimble jellyfish that are everywhere you want to be in the Caribbean in the warmer months. But the airline lost that bag on the way down.

About the only thing Hopper wasn't prepared for was hostile locals. Our first night in the islands, at a bar near our Tortola hostel, he was laying it on thick with Simon, the bartender, perhaps hoping we'd get a few free drinks, when this good-looking Australian woman overheard us talking about our swim.

“Really?” she joined in, pleasantly enough at first. “That doesn't sound very hard—only a few miles between them.”

“I know,” Hopper answered. “Although everybody else we've told hasn't believed us.”

“It's just 20 miles in a few days,” I added. “Anybody could do it.”

I was about to get up and stand closer when her entire expression changed. It reminded me of a look my high school water-polo co-captain would get before kicking me in the balls.

“You're liars,” she spat out, but she wasn't done. “You're not swimming anywhere. Nobody'd be that stupid. Do you know anything about the currents between the islands? You can't swim against them. I've dived in there enough to know. You're a bunch of wankers.”

“Oh, no,” I replied, raising my eyebrows. “We're definitely doing it.”

“Fuckers.”

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.

AT SIX O'CLOCK THE NEXT MORNING, I wasn't so sure. We were leaving Virgin Gorda for the four-mile swim to Ginger from the Baths, a boulder-strewn volcanic peninsula that looks more like Joshua Tree than the Caribbean. This was where, according to the Australian woman, we'd have our asses handed to us: The ocean has had thousands of miles to build up its tempo here before it pounds the rocky beach. Indeed, beyond the rocks, I was sure a hurricane waited for us. I felt like I could see shark fins, roiling whitecaps, and marauding speedboats everywhere.

“Hey, Hod,” Hopper called, casually treading water beside me. “What a perfect day to begin our journey, huh? Let's get going, though. Get this under our belt.”

“Yeah, you guys go,” Paolo said from the safety of his speedboat, which wasn't turning out to be so speedy. Not only was it impossible to start, it also wouldn't plane. We'd be half eaten by the time they ever got to us.

Thankfully, Saint Jude, patron saint of lost causes, was smiling down on us: The winds were out of the east-northeast instead of the prevailing southeast, and both the water and the sky were clear and warm. And a chain of rocky islands guards much of the crossing from the Baths to Ginger, blocking the east wind and creating shallow water most of the way.

We didn't see much. Millions of tiny glistening fish streaked along the surface, so small they seemed more optical illusions than aquatic life, and a couple of barracuda swam urgently toward us and then appeared to back up when they saw our size, as if thinking, Oops—my bad. That was it, if you discount the hundreds of jellyfish attacking us. For an animal that has no brain, bones, eyes, or heart, the thimble jelly is a tricky little predator, filled with stinging cells called nemocysts that inject their venom into you with teeny-tiny harpoons.

As the minutes, a half hour, and then an hour ticked off and the water got deeper and deeper, I grew ever more freaked out, despite our mother hens, Paolo and Derik, constantly hovering within a few hundred yards. For some reason, I was most afraid of sharks in the deeper water, although most attacks happen in shallow areas and, even more pertinent, my own not-so-casual research showed that there have been only four unprovoked shark attacks in the Virgin Islands in the past 100 years. Even so, I took comfort in the fact that Hopper was in the rear, pulling the surfboard.

Suddenly, Hopper stopped swimming. We were about a quarter-mile off Ginger Island in 100 feet of water. Not a good place for a chat.

“We gotta do something different,” he said, taking a swig from the water bottle strapped to the board.

“Why would we do that? Let's keep going,” I answered, a little pissy. “We're nearly there.”

“We're not going anywhere. I've been watching that white scar on the cliffs over there for ten minutes. We haven't moved.”

Now that we were no longer in the lee of the outlying islands, those whitecaps I'd imagined had become very real, along with an accompanying 15-knot wind. The one-knot current our chart indicated was more like two to three. Our destination on Ginger—a lagoon behind a northeast peninsula—was now upwind.

We strapped on our Zura Alphas, flexible, lightweight fins that would give us just enough of an advantage to compensate for the wind and current. Except they didn't. We swam for another ten minutes, but we were still going backwards.

Clearly outpowered, we decided to put the wind on our port beam and head for the less desirable north shore, where there appeared to be a boat anchored. Fifteen minutes later, we tumbled ashore, arriving like bewildered shipwreck survivors as breakers sent us rolling over spiny sea urchins. What had looked like an inviting beach 400 yards away turned out to be a 15-foot-wide shelf of broken coral. And the boat that was going to be our salvation was actually a wrecked charter sailboat, itself forlornly waiting to be rescued.

That's how we spent our afternoon—forlornly waiting. While Paolo and Derik went back to Virgin Gorda to get their boat fixed, Hopper and I swam another mile to the western edge of the island and generally wilted in the inescapable sun. That evening, they finally returned with food, drinks, and a still-broken boat.

“Well, day two down and no shark. That's a good thing,” I said, toasting with a shot of rum-spiked Gatorade.

Derik looked at Paolo, as if to ask, Should we tell him? “Paolo did see this really big thing come up behind you once.”

“Really big,” Paolo said, smiling.

That night, camping through two storms on the beach without a sleeping bag, rainjacket, or even a tarp, I dreamed of shark-shaped jellyfish eating holes through my sodden brain. About the only thing that made me happy was watching Hopper hiding from the rain, huddled under a fish crate.

THIS CARIBBEAN SWIMMING was really paying off as far as my Olympic dreams were concerned. My shark phobia had me concentrating like never before on making my stroke smoother, and soon I was sliding through the water like a slippery, unappetizing eel.

Day three was a short two-mile but deep-water swim from Ginger to the Cooper Island Beach Club. Practicing good stroke mechanics and head positioning, I would stare straight down, and what I saw wasn't pretty; it was gorgeous, an endless expanse of dreamy blue water that made me think of exploring deep space. I knew I was looking at least as far as 40, maybe 50, feet deep, but the milky blueness was so uniform in this 120-foot water, I couldn't see anything. No bottom, no fish, no nothing, except for an occasional terrifying strand of seaweed darting into view that never failed to make me jump.

Slowly, though, we were developing a certain rhythm—and not just in the water. “I've figured out the ebb and flow of this trip,” Hopper said the next morning while I fried up a batch of holes-in-the-wall in our little kitchenette at the down-to-earth resort. He was looking and sounding a little stressed. I was feeling the same. “The tension builds as the swim approaches,” he went on. “You're wondering about the variables, the current, the wind, boats, et cetera, and then you're a little bit freaked out when you first shove off. Things start to mellow as your arms loosen up. You're under way. Life is good. Then you arrive and you're all elated. You have a beer, sleep, go over the swim, and then it's just . . . a slow . . . build . . . toward . . . that . . . pre-swim tension.”

The best part of swim-trekking was that, unlike 99 percent of the swimmers in the world, we actually arrived somewhere at the end of our workouts and talked to real people. As five-time Olympic gold medalist Gary Hall Jr. puts it, “It's bad enough talking to the stripe at the bottom of the pool. It's even worse when it starts talking back.”

On Salt Island, a brief stopover between Cooper and Peter islands on the grueling fourth day of our voyage, we came ashore to find a skeletal elderly man wandering outside the ramshackle cinder-block huts that clutter the shoreline, looking somewhat befuddled in his slightly askew construction helmet. His name was Henry Leonard, he said, and he lived there all by himself. There used to be families scattered all over the one-and-a-half-square-mile island, he explained, collecting salt in the inland ponds. Now it was just him, the rustling palms, and the salt, which stretched behind his shack in a long, uninterrupted sheet of gray. We talked for a few more minutes, but then we too had to shove off.

The six-mile Cooper-to-Peter leg was our longest by far, almost the equivalent in effort of running a marathon. And here it was already 10 a.m., and we still had four miles to go. Hopper and I swam off without Paolo and Derik, but after half an hour and no safety boat, Hopper tapped me on the shoulder. “What do you want to do?” he asked. “Turn back? Wait here?” Surely they'd show up any minute.

Mere seconds later, I was staring again into that never-ending nothingness, screaming to myself, Turn back! This is how it's gonna end! But I kept swimming. After about an hour and no bites to our soft underbellies, I noticed that I was no longer jumping like a frightened surface minnow at every perceived attack. I even started hoping that Paolo and Derik wouldn't show up. I was feeling like part of the ocean, as if I actually belonged in it instead of being a temporary, wary visitor. The wind, now stronger, pushed us down the ever-towering swells. I was Aquaman, Johnny Weissmuller, and a dolphin rolled into one!

I was so happy that I didn't even mind the harbor attendant yelling that we couldn't swim near the boats at the Peter Island Resort dock. When we explained to him that we were a boat, he just waved exasperatedly toward a ladder near a sybaritic 50-foot cruiser.

The worst swim was over, and the most dangerous part of our adventure would turn out to be the safety boat, which in fact sank to the bottom of the ocean as Paolo and I scrambled to salvage his gear a day later. But for now, what'd we care? High on endorphins, we zipped around Peter Island's luxurious digs, playing on Hobie Cats, downing more rum, and getting massaged on a hilltop overlooking nearly all the Virgin Islands. And we were just one day away from the ultimate spring-break party.

OUR LAST MORNING, we had a following breeze, making our final goal—a floating bar called Willy T's—absurdly doable. The William Thornton, a 100-foot steel schooner moored in a bay called the Bight on Norman Island, is party central for the Virgin Islands. A place where women jump naked from the railing to get a free T-shirt and men get drunk. “No matter what you do,” one friend had demanded, “you gotta finish at Willy T's.”

It was a five-mile swim that felt like less than one. Time in the water no longer represented worrying about survival. It was simply what we did—where we belonged. We were the SwimTrek BVI! boys, and the ocean was our playground.

When we rounded Water Point, a jutting peninsula on Norman's northwestern edge and the entrance to the Bight, we passed over some divers 40 to 50 feet below us—a surreal experience, to suddenly run into other humans flippering through our sea. Their bubbles bumped into us, drifting to the surface. And then we saw Willy T's itself, about a third of a mile away on the far side of the bay. Without exchanging a word, we decided to race that last stretch to touch the hull, which we did, simultaneously.

“We just swam from Virgin Gorda!” Hopper announced. He was answered with cheers and a couple of free beers.

Zeus, the horniest bartender outside of Tom Cruise in Cocktail, poured us a couple of painkillers—double shots of rum hidden in a masterly mix of coconut, pineapple, and orange juices—when we made it up to the bow. Actually, that first beer had gotten to me, so I don't know if the bar was in the bow or the stern, but I do know it was near an end.

As the afternoon passed, more and more revelers arrived by boat—beers in hand, bodies bobbing to the bar music, heavy on rap, reggae, and sexy R&B. Even the women seemed like predators, waiting to see who would get the most debauched. Silent old men (older than me) stood along the railing, praying somebody would go for a T-shirt. As we got drunker, Zeus seemed more and more impressed with our swim, but when I asked if we could get free T-shirts, he said, “No way, man. That's for the women, and there's only one way they're getting them: They've got to show Zeus the stuff.” Then he turned up Kanye West so loud that even the sea seemed to vibrate.

As if on cue, an attractive newlywed from South Carolina zipped up in a boat with her husband and, after downing a few of her own painkillers, got herself a tattoo. This required the bride to lift her shirt, so that Zeus could lick the skin just above her left nipple. You know, so he could wet a spot for applying the tattoo. Her husband, powering down a Red Stripe, yelled out, “That's what I'm talking about!”

I chugged down another painkiller, gave Hopper a kiss, and smiled, a contented man. The SwimTrekkers had finally found the real spring break.

Oh, and as far as my Olympic hopes go? Thanks to all that BVI mileage, I got even faster—I'm less than half a second off my best time in the 50 free. It's Beijing or bust, baby—as long as they have beer bongs over there.