The Everly Brothers’ ballad booms from a pair of stereo speakers mounted in a thatched-roof bungalow. Down the beach, a huge wind gong is gently vibrating. A few feet away, the Caribbean glistens in the last yawn of twilight.

I’m enjoying an alfresco dinner of oysters and mango shrimp, sitting beachside with my host and three new friends. There is a tangle of tropical jungle behind us. And we’re watching the sun sink over the horizon as prisms dance across the seascape.

I am, as it happens, a guest on the private island of Johnny Depp. For reasons that surely once made sense, this 45-acre Bahamian dollop appears on maps as Little Hall’s Pond Cay. And this idyllic stretch of sand has been re-christened by the actor as Lily Rose Beach, after his 10-year-old daughter. We are surrounded by silver buttonwood, mangrove thickets, flowering plants, and a huge coconut tree about to drop its fruit. Tiki torches flicker in the shadows. Nearby, a long-abandoned Haitian-refugee skiff lies on its side like a giant melon rind. The relic is a reminder that the dreamy Caribbean, for all its dazzling, blue-green hues, has always swelled with menace and mystery and broken lives.

Depp raises a daiquiri glass and toasts the parting sun with Havana rum. Whenever I want you, all I have to do is drea-ea-ea-ea-eam…

In this particularly calibrated paradise, every detail has its subtext—of Depp’s own devising. Even though the song that wafts from the speakers is clearly the 1950s hit “All I Have to Do Is Dream,” the raspy voice sounds like nothing so much as the howl of a prisoner in a torture chamber.

“That’s Keith [Richards]!,” Depp enthuses. “He recorded some of these after his 77 heroin bust in Toronto. He thought he was headed to jail for 30 fucking years for trafficking.”

Depp, as if recounting a favorite outlaw fable, then goes on to tell how the Ontario Provincial Police and a team of Royal Canadian Mounties stormed into Keith Richards’s room while he was sleeping and confiscated 22 grams of heroin. (Richards eventually had his sentence reduced from trafficking to possession and was put on probation for a year.)

Depp tilts his head toward the hut. “Listen to this,” he urges, nodding in adoration. Richards, alone on piano, is now singing a haunting rendition of Hoagy Carmichael’s “The Nearness of You.”

“I played this one from a boom box when Lily Rose was born,” Depp says, referring to the day a decade ago when his partner, Vanessa Paradis, the French-born singer and actress, brought their daughter into the world. “This is her birth song. She arrived to this, man.”

Welcome to Deppville. It’s a place where the off-kilter meets off-road serenity, where pure spontaneity meets fastidiously manicured fantasy. I’ve joined my suave-hillbilly friend for a week in the tropics to escape the bad noise of March. With Wall Street plummeting and Detroit sliding toward the abyss, a seafaring adventure in the Atlantic feels somewhat sinful. But so what? I’d just finished writing a 900-page book on Theodore Roosevelt and needed a spring break.  And so, when Depp called to insist that I join him, he had me, hook, line, and sinker. (Both Depp and I were close friends of Hunter S.  Thompson, the father of gonzo journalism, who took his own life in 2005; I serve as the literary executor of Thompson’s estate.)

Along for the ride are three of Depp’s best friends and work associates: Stephen Deuters, a 30-year-old music archivist from West London with a mane of shoulder-length hair and the mien of a youthful Mick Jagger; Nathan Holmes, a deadpan comedian out of North Yorkshire, aged 34, who worked with Depp on Tim Burton’s Sleepy Hollow; and Keenan Wyatt, 44, of Phoenix. A stocky six feet three inches, Wyatt, a sound technician, serves as Depp’s adviser, bodyguard, and well-mannered enforcer, prone to spouting pearls such as “Toughen up, princess,” for comic effect. (Depp is a spry 46.)

The five of us convened in Los Angeles, then flew to Nassau on a chartered jet. Boarding Depp’s 156-foot yacht, we set off for Little Hall’s Pond, 60 nautical miles to the southeast.

Depp has named the vessel Vajoliroja, a fairly unpronounceable construct jury-rigged from the first two letters of the names of his four family members: Vanessa, Johnny, Lily Rose, and seven-year-old Jack. The Vajoliroja—an elegant, steam-powered motor yacht, built in 2001 in an early-20th-century style— has become Depp’s floating salon, garret, and getaway. The yacht has a formal dining room, a master suite, and four guest cabins. The coed crew of eight, from six nations, is quartered farther belowdecks.

Registered in the Bikini atoll, the ship flies the colors of the Marshall Islands—alongside a mischievous Jolly Roger. And why not? Revenues from the three Pirates of the Caribbean movies—in which Depp played the highseas brigand (and Keith Richards-inflected) Captain Jack Sparrow, earning him Oscar and Golden Globe nominations—have certainly helped to pay the bills.

Because Depp has the eye of an interior decorator, virtually every object aboard the Vajoliroja has the actor’s signature. (He hired designer L. M. Pagano to create the jewel-box decor of indeterminate era: Orient Express by way of Parisian brothel.) Maroon is the dominant interior scheme, from the chairs to the chenille-covered settees. The carpeting is a swirl of deep blue and sea green. Buccaneer touches abound: the draperies in the master suite, for instance, resemble pirate hats. Here and there are walnut cabinets, paneling of Honduran mahogany, bulging bookshelves with Modern Library classics, and old walking sticks, including one with a wooden rabbit head possessing shiny yellow eyes. “Anything too modern,” Depp decrees, “would throw things out of whack. It would kill the time travel.”

Ever since Depp and I co-wrote the soundtrack liner notes for Gonzo (director Alex Gibney’s documentary about Hunter Thompson, produced by V.F. editor Graydon Carter), we had discussed a Caribbean jaunt. Our defining motto, we had vowed, would be the one adopted by Depp’s film company, Infinitum Nihil—a thesis plucked straight from the pages of Tolstoy’s midlife-crisis memoir, A Confession: “Force is force, matter is matter, will is will, the infinite is the infinite, nothing is nothing.”

Our principal goal: to explore the island, dally in the Exumas, and reach San Juan, Puerto Rico, in time for Depp to start production on The Rum Diary. The film, based on Thompson’s autobiographical novel, follows a love-struck and rather degenerate freelance journalist who happens to be in Puerto Rico in the late 50s, around the time Fidel Castro takes power in Cuba. Depp can mimic Thompson with dead-on accuracy, a feat he proved in the 1998 screen adaptation of Fear and Loathing in Las Vegas, in which he played Thompson’s alter ego, Raoul Duke. For The Rum Diary, Depp claims, he hopes to interpret the Hunter character as a sort of booze-salted Bogart. San Juan will serve as a Casablanca backdrop.

“No ‘Extreme Hunter’ like I did in the Vegas movie,” Depp says. “The Hunter of that film was somewhat hyped. Hunter was upset with me, initially, with the crooked walk and stance. ‘God,’ I said to him, ‘the thing is what it is.’ And he understood that. All became fine. Now I’m trying to get at the essence of the young Hunter. Everything he said was so fucking funny you had to write it down. I loved throwing a word into the mix he liked. I remember one time saying the backwoods version of the word ‘quietus’ [kwuy-ate-us]. ‘Did you say, “kwuy-ate-us”?,’ Thompson asked. And I said, ‘Yeah.’ Hunter said, ‘Fuck, I haven’t heard that word in years.’ We figured out it was a regional Kentucky thing. But we liked trying out special words.”

The multi-talented Depp is also an artist. “What I love to do is paint people’s faces, y’know,” he says. “Because you want to find that emotion, see what’s going on behind their eyes.”

Depp has spent much of the last year living in Chicago making Public Enemies, a film about John Dillinger, opening in theaters this month. Set in the 1930s, when America was in the maw of the Great Depression, the script is based on the book by Vanity Fair special correspondent Bryan Burrough about the Indiana misfit turned bank robber, sex symbol, and world-famous fugitive. In these dire financial times, what could be more appealing to audiences than an action-packed movie about banks getting their comeuppance in the heartland?

Fittingly, Depp was born in Owensboro, Kentucky, 160 miles from the Mooresville, Indiana, farm where Dillinger lived as a teen. “When I was a little kid,” the actor says with a laugh, “I had no idea he was from practically next door.” While director Michael Mann, according to Depp, kept trying to get his lead to sound like some stereotypical mobster—a hybrid of George Raft and Tony Soprano—Depp had another notion. A self-described “research hag,” he scoured archives for recordings of Dillinger. When nothing surfaced, Depp dug deeper and discovered audiotapes of Dillinger’s father, John Wilson Dillinger, a farmer and grocer by trade. “The closest I could get was basically listening to his pa,” Depp said. “There were some recordings which sounded exactly like my relatives. I mean, his pop sounded like my grandfather, almost exactly. So I just made the decision to sound not aggressively southern but to adopt a bit of a drawl.”

To prep for Public Enemies, Depp visited Dillinger landmarks such as the Little Bohemia Lodge, in Manitowish Waters, Wisconsin (the site of a botched 1934 F.B.I. shoot-out, from which Dillinger escaped unharmed), and the Biograph Theater, in Chicago (where the gangster, after watching a Clark Gable film, was finally gunned down by the F.B.I.). The audacious Dillinger, even as the feds had an all-points bulletin out for him, brought his girlfriend to Wrigley Field to see the Cubs; Depp took in a day game to get a feel for the ambience of the 1914 ballpark.

In San Juan, Puerto Rico, Depp prepares to shoot his next film, The Rum Diary, in which he’ll channel a young Hunter S. Thompson.

Scenes from Public Enemies were filmed outside Stateville Correctional Center, near Joliet, Illinois. The maximum-security facility—where inmates are sometimes locked down 24 hours a day, for days at a time— is considered the end of the line in Middle America. The prison board gave Depp an impromptu tour, taking him right into the Round House, a four-story cellblock with a panopticon guard tower in the center.

“We walked in there and it was a very frightening feeling,” Depp says, becoming especially animated. “It was full lockdown. The inmates started screaming, ‘Hey, Captain Jack, get me out!’ And stuff like ‘Help me escape, Captain Jack! You can do it!’ Shit like that. These guys went wild….It was unbelievable.”

Fortuitously, a Stateville historian unearthed a mug shot of Depp’s stepfather— Robert Palmer, who died in 2000—in the prison files. For Depp, the memento was a revelation. “He’d done some burglaries, robbery—you know, that kind of thing,” Depp says. “He was in Midwest prisons from his youth up until he was a full-grown man. Yeah, so I got to learn a bit more about my stepdad and his college years, as it were.” According to Depp, Palmer was a handsome ne’er-do-well, a flinty combination of Robert Mitchum and the young George C. Scott.

Depp insists on one rule for his roles: the personalities he plays must be his imaginative creations. Throughout his career, he has brought a string of otherworldly characters to life: Edward Scissorhands, Ichabod Crane, Jack Sparrow, Willy Wonka, Sweeney Todd. Next year he will appear as the Mad Hatter in a screen version of Lewis Carroll’s Alice’s Adventures in Wonderland (in what will be his seventh collaborative project with director Tim Burton). Each portrayal has sprung from deep within his psyche. Moreover, many of his characters exist at a remove from civilization, in some parallel Little Hall’s Pond, where fantasy, not reality, has the upper hand.

And yet when Depp plays an actual person—such as Ed Wood, George Jung in Blow, Sir J. M. Barrie in Finding Neverland, and the iconic Dillinger—he tries to honor their true biographies, right down to their aftershave brands, believing he might actually summon a semblance of his characters’ souls. “There’s a certain responsibility playing a guy, even Dillinger,” Depp says. “You want to do him right, ya know. You don’t want to let him down. He may be watching. So I don’t want to water down the integrity of the person I’m playing. I want to find its essence. Sometimes [period] music helps me channel.”

Although Depp, eons ago, had filmed a television episode in Chicago, Public Enemies was his first prolonged exposure to what has since become his favorite American city. “Everybody [in Chicago] treated me normal,” Depp says. “They’d say, ‘Hey, Johnny,’ then left me alone.” Depp regularly drank at the Kerryman, an Irish pub and restaurant at Clark and Erie. He ate at Gene & Georgetti, the famed Chicago steak house, set snug under the El tracks. “I visited the Art Institute and the Chicago Music Exchange. I loved looking out the car window at all those incredible neighborhoods and architecture.”

Throughout the filming, Depp played Artie Shaw’s 1938 recording of “Nightmare” a dozen times a day. (This habit continued, to a lesser degree, on the Vajoliroja) “It broke through every bad mood,” he says of the brooding and bracing song. “Somehow its power, brashness, and piercing sound helped me to stay focused.”

And to tap his inner Dillinger, he fired guns constantly. “All [of our] weapons in Chicago were taken care of by Harry Lu,” Depp explains. “He’s our genius armsman guru. We worked together on the pirate films. He’s incredibly knowledgeable. We went out to a range and tried various magazines and drums, and I got to fire live rounds out of a Thompson submachine gun for days on end. It was, I mean, a kid’s dream come true. I grew up firing guns since I was five or six years old, so for me it was like going back home.”

When I ask Depp why, like many Americans in the 30s, he cheered for the bank robber over the F.B.I., he smiles. “Come on,” he says. “You know I’m always for the Indian in the cowboy movie. Always.” Depp, who is part Cherokee, says he has been considering signing on to play Tonto in a Disney remake of The Lone Ranger. “Tonto needs to be in charge,” Depp says, half in jest. “The “ Lone Ranger should be a fool, a lovable one, but a fool nonetheless.”

As our voyage gets under way, Depp speaks of the need for escapism in a world gone wrong, How does the individualist, he wonders, find dignity and purity in a plastic culture and a polluted world? “Little Hall’s Pond is my decompression,” “ he says. “It’s my way of trying to return to normalcy. There is a period once you finish a guy—a character—when you’re looking to go back to yourself, and sometimes it can manifest illness. I mean, after I made The Libertine”—in which Depp plays the debauched Earl of Rochester—“I was in bed for two weeks. When you’re working, you don’t get sick, then suddenly it hits you like a two-by-four. After Dillinger, my head was done in. I needed to escape. So being able to get on the boat and move allowed my head freedom again. Escapism is survival to me.

Clowning for the camera, Depp pecks a bride’s picture on the side of a San Juan laundry van. “What interested me was that he has so many faces,” says photographer François-Marie Banier, who has known Depp for 20 years. “But each one is completely pure and innocent.”

“Somehow,” he says, “the mathematics led me here to my island. I don’t think I’d ever seen any place so pure and beautiful. You can feel your pulse rate drop about 20 beats. It’s instant freedom. And that rare beast—simplicity—can be had. And a little morsel of anonymity.

“Lily Rose,” he marvels, “actually got to put a message in a bottle and watched it drift, drift away to a neighboring island, [and the finders] set up a treasure hunt for [their] kids. Whenever I was getting frustrated about being ‘novelty boy’ and making movies, I told myself, Calm down. I can come down here and disappear. I spent the Christmas season here with Vanessa and the kids. You can feed hot dogs to the nurse sharks in the Exumas—but it’s best to not swim when doing it.”

The captain of the Vajoliroja is a New Zealander named Graeme Brown, who knows the cays like a park ranger. He explains that the Land and Sea Park, near Little Hall’s Pond, is the world’s first such protected reserve, established 51 years ago. “It’s a no-take zone,” Brown says, rubbing his gray-speckled goatee. “You can’t remove any living creatures. It’s a replenishment center for conch, lobster, and other over-harvested species.”

Brown lifts anchor and sets sail, piloting us out of Nassau harbor to the west, around the western end of New Providence, and southeast to Highborne Cay. We next head due south toward Little Hall’s Pond Cay, the winds a light 10 knots.

While Brown may be the captain, Depp is the commander of the ship, which he oversees like the starship Enterprise. He decides on everything from the dinner menu to the navigational route. He is also the resident mix master, programming (through the ship’s sound system) the appropriate tune for every occasion. Die-hard rock ’n’ rollers, in fact, consider Depp an audio savant and musical talent—for his facility on guitar. On board, Depp spins Tom Waits, Bright Eyes, Bob Dylan, Johnny Cash, Iggy Pop, Warren Zevon, Tom Petty, James Booker, the Nitty Gritty Dirt Band, and R.E.M., along with an earful of the Australian band Augie March, whose lyrics he regularly recites aloud.

Depp is also keen on the Meet Glen Campbell CD, recently released by the 73-year-old pop and country star. “When he sang ‘Galveston’ years ago, it killed me,” Depp says, describing the Jimmy Webb song that Campbell transformed into a Top 10 hit in 1969, making it his own. “It’s about a Vietnam soldier dreaming of home. It’s elegant and perfectly timed.”

Augie March… and Artie Shaw? Keith Richards … and daiquiris? The Depp dichotomy generates a boisterous, seesaw spirit. Somehow it makes sense in this bifurcated culture to see the Disney cash cow emblazoned with enough tattoos to give Flea a fright. Or to hear Glen Campbell being championed by the swank nightclub impresario. (Depp and partners opened L.A.’s infamous Viper Room in 1993.)

Being in a ship,” Samuel Johnson wrote, “is being in a jail with the chance of being drowned.” Depp doesn’t quite see it that way. In the vastness of the Caribbean, all of his anxieties melt away. He considers the ocean a force of strength, just as his island is his patch of sanity. In escape, he recovers and discovers and stabilizes.

Around Saint Patrick’s Day, the Atlantic turns a bit rough. I sensibly reach for “the Patch” to calm my stomach, and Holmes gobbles Dramamine like Tic Tacs. Deuters simply tries his damnedest not to turn green. Depp and Wyatt, however, down can after can of Guinness as we ride the waves. “What would be fun,” Depp reiterates during my bout of queasiness, “would be getting Guinness on tap for the island.”

Depp, from the moment we board, goes full tropic. Barefoot and goateed, he wears blue-tinted shades and a purple bandanna embroidered with the words “The Brave”— a keepsake from a picture he made with Marlon Brando in 1997.

From time to time, the individualist in him gripes about the political correctness of modern-day Hollywood. He pines for the old iconoclasts. “Where is our generation of Dean Martins and Frank Sinatras?” he asks. “And the Georgie Jessels and Walter Brennans?”—referring to two of the town’s arch-conservatives of yore. “I want Tiny Tim and Bix Beiderbecke back.”

In the Hunter Thompson days, out in Colorado, Depp smoked Bali Shag tobacco like a fiend. Rolling his own had become almost a trademark for him in the 1990s. “I gave it up a few years ago,” he says. “I said, ‘Fuck it—I don’t need those things.’ ” Every morning now, Depp does yoga. He’s remarkably averse to conflict, pruning the toxic people from his life. His 48-year-old sister, Christi Dembrowski, is his closest adviser and friend (and the producer of The Rum Diary). Together, they run his production company. “Basically, Christi has kept me alive,” Depp says. “I’m really like a blind mole, and she just leads me around, making me do the right thing, or I’d just fall off the cliff. She’s like Superwoman.”

The memories of Depp’s two late mentors—Brando and Thompson—fuel his Uber-hubris. He still savors the folk wisdom they imparted. “Selfishly, what I miss about Hunter isn’t the Too Much Fun Club stuff,” Depp says. “It was his steady advice. His radar detector was spot-on. He knew instantly if he didn’t like somebody.”

Around Depp’s neck is Thompson’s logo, as it were: a medallion that consists of a little dagger descending from a clenched fist bearing two extended thumbs. Set in the center is a red stone representing a peyote button. Naturally, within a day of leaving Nassau, all of Depp’s chest is sunburned except where the pendant has shielded his skin. “That bastard Hunter has branded me,” he jokingly complains. “He made me fall asleep in the sun.”

Crosby, Stills & Nash are serenading us over the yacht’s speakers when we first spy Depp’s Caribbean Oz. As we approach, the water surrounding the tear-shaped isle is so clear that the land seems to be floating on the surface. At this point, there is no terra firma visible to the east of us, just the vast Atlantic. The sun has coppered our faces. As shorebirds fly overhead, we sit under shady awnings and get ready to drop anchor.

At first glance, the island appears to be a terrarium surrounded by the whitest beaches imaginable. Comparing it to another of his six homes, a villa in Provence, Depp points to his property like a proud farmer and declares, “Both our place in France and Little Hall’s Pond look as [they] probably did 100 years ago. The most satisfying part about both is their consistency.”

Little Hall’s Pond has six different beaches— Paradis, Gonzo, Brando, Lily Rose, Jack, and Utility—each with a personality and cove of its own. There are small residences scattered casually about; all are solar-powered. Conveniently slung hammocks sway in all the right places (i.e., away from the poisonwood trees). Transportation on the island consists of a fleet of green golf carts. “My hillbilly instinct tells me,” Depp says, “when you’re ready to drive a golf cart, you should have a beer.”

We light into a case of Coronas and take a large inflatable raft to Lily Rose Beach. The water is warm but refreshing. A soothing breeze ruffles the palms and mangroves. Bright-red hibiscus and wild poinsettia lend a sweet, almost jasmine scent. We pause to watch thumb-size hummingbirds feed on pigeon-plum plants and look for five-foot-long Iggy, the island’s lording rock iguana. “Iggy has found a mate,” Depp informs us with a lopsided grin, “and the island will soon have babies.”

Depp is particularly eager to show me Gonzo Beach, named in honor of Thompson. Depp, Wyatt, and I rumble off in a golf cart as the others bring up the rear. Five minutes later, we arrive at what Depp calls “the most savage and exposed of all the beaches. Gonzo Beach is pure Hunter.”

It really is. The furniture, arrayed across the sandy cove, features glass tables with Thompson’s face etched in the center. We sprawl on driftwood benches. A lone seaplane hums overhead as bananaquits chatter sweetness. Depp directs our attention to a pocket of water 200 yards away—a prime spot for seeing tropical fish and reef plants. In the Caribbean there is a single rule: the lighter the shade of blue, the more shallow the water. Like a kaleidoscope shifting its tints of color, the waters turn from jade to sapphire, amethyst to emerald, by the hour. No old scows or new ferryboats mar the view. Indeed, no boat traffic at all dares to cross Depp’s protected, postage-stamp paradise. “I want to be Ruler of the Exumas,” Depp confesses, with a grin. “I like the sound of it. I want to become Kurtz and live like in Lord of the Flies. And like the novelist J. P. Donleavy, I’ll get Guinness on tap here. Man … I could lead an Exumas revolution and become the Che Guevara of the chain.”

But turmoil is hardly the attraction here. Instead, it’s the way present and future, light and distance, space and darkness all bend and blend together. “The truth is,” Depp says, “you want to come here and read Finnegans Wake until you understand it.”

Leaving the scrubland around Gonzo Beach, we drive to the other side of the island, where a yurt has been constructed out of bamboo. Inside, the decor is Trader Vic’s Polynesian. The beach floor in the bedroom has sand as fine as talcum powder.

Depp recalls a conversation he had with Brando in 1994, when Depp was poised to purchase Little Hall’s Pond. Instead of expressing outright enthusiasm, Brando—who once lived on the French Polynesian atoll of Tetiaroa—asked a series of pragmatic questions: “What’s the elevation? How protected are you?” Brando, according to Depp, was being sensible, focused, and paternal. “With hurricanes and all,” Depp says, “he just didn’t want me to make a mistake.”

Back on the golf cart, Depp is starting to careen like a Roman mo-ped driver. Limbs shift. Bones rattle. As my host grinds the cart up a steep mountain path, I realize that Brando needn’t have worried about elevation. I also notice black bees and tiny scorpions.

At the summit, we reach a ranch-style house with a stunning 360-degree view. A telescope is trained on an island called Osprey Bird Rock; Depp owns that too. Playing host, he opens up more Coronas, slices limes, and sticks them into the longneck bottles. We sink onto sofas and take it all in. Soon, we are laughing out loud at some framed trinkets on the wall: a friend of Depp’s has taken mock Exumas currency and created counterfeit $20 bills bearing the face of Captain Jack.

In a quiet interlude, Depp stops and regards the sea outside. “I defy any painter,” he says, “to capture those shades of blue. I was just lucky this place found me.”

The snorkeling around Little Hall’s Pond is world-class. One afternoon, we sail to the east end of the island, drop anchor, and slip overboard into the turquoise calm of Heath’s Place (named after the late actor Heath Ledger). We see an explosion of marine life. Fish, bedecked in Ken Kesey neon, dart about in every direction. We study fin arrangements and Day-Glo markings, diligently looking them up in our Reef Fish reference book. Even the nurse sharks appear benign, though I know enough to keep on my guard, even in this peaceable kingdom.

“Oh shit,” Depp shouts, lifting his snorkeled crown above the waterline. “A barracuda! Come look! It’s the only species more frightening than a terrier dog.” Who but Johnny Depp would consider it a form of sport to wade with the barracuda? I swim back to the raft feeling a touch asthmatic— and, frankly, scared.

“Nobody is going to ever ruin the Land and Sea Park,” Depp later insists. “It’s like a rare gem, a diamond. I look forward to my kids growing up on the island, spending months out of the year here… learning about sea life and how to protect sea life… and their kids growing up here, and so on.”

One night we take the tender and head west out onto the water to witness the launch— about 300 miles away—of the space shuttle Discovery as it ascends into the evening from Cape Canaveral. The sky bulges with stars, which seem so finely etched that it’s hard to imagine the Exumas could ever experience the pitch black of a moonless night.

We wait, eyes heavenward. We wait some more. Around us, plankton causes the water’s surface to give off a gleam of eerie phosphorescence. With our flashlights aimed into the vodka-clear Caribbean, we see a school of large yellowtail jack circling around us. Suddenly, a luminous cloud rises in the sky. It is shaped like an anvil, emitting the kind of incandescent gas you’d find on some distant star. The shuttle soars, in total silence, into the bejeweled black. We are transfixed by strange light, both above and below. We feel privileged to be alive in the Caribbean Basin in the Year of Our Lord 2009.

“Theoretically,” Depp says, “this place can add years to your life.” Then he quotes the old adage: “Money doesn’t buy you happiness. But it buys you a big enough yacht to sail right up to it.”

Sometimes, when Depp creeps around the Vajoliroja, he reminds me of Charlie Chaplin. There is a shyness about the way he floats in and out of a room. His depth of character and his open, compassionate bearing are genuine. He has an insatiable curiosity about everything.

As our conversation turns to the Shakespeare and Company bookshop in Paris—where I clerked for a summer in my 20s—the Sweeney Todd side of Depp emerges and he grows a bit gruesome. He asks Keenan to cue up a macabre video on the wide-screen TV showing George Whitman, the bookstore owner, burning his hair with a candle to impress a few artsy girls. (The clip is available on YouTube under “George Whitman, Burning Head.”) “And then George reads them poetry!” Depp laughs approvingly. “Poof! Look at that clump of sodden hair.” I can almost smell Whitman’s singed tufts through the flat-screen.

As a nightly ritual, we watch movies and YouTube clips during sumptuous meals. Because there is a chef aboard, we’ve eaten like kings—kings, that is, of the Kappa Sigma frat house. The menus consist of grilled beef-and-cheese sandwiches, raw oysters, Chicago-style pepperoni pizza, and turkey-chili tacos with guacamole. There have been heaping salads with fresh seafood. And plenty of Red Bull.

For all our light boozing and clowning, we realize we’re all hopeless homebodies, returning repeatedly to discussions about our kids. (The voyage has been surprisingly free of locker-room talk.) Depp, in particular, tries to spend as much time with his 36-year-old partner, Vanessa Paradis, as possible—despite his acting regimen and her busy schedule as an actress, singer, model, and mother—and says he’s determined to make sure Lily Rose and Jack live like Tom Sawyers as long as they can.

Our entertainment, like the decor, exists in a sort of time warp. We sample James Brown on an old video of CNN Sonya Live in L.A. wearing Sly Stone glasses the size of a scuba mask. “This is as high as you can get,” Depp declares, “unless you go on ether.” Depp is a huge fan of the 1970s Dean Martin TV roasts with Don Rickles, so we consume them by the hour. The old comedian Foster Brooks, whose shtick was sham inebriation, can almost move Depp to tears. We also watch A Colbert Christmas, largely to see Willie Nelson in the Three Wise Men skit. We screen Where Eagles Dare (Richard Burton and Clint Eastwood) and Tropic Thunder (Ben Stiller, Robert Downey Jr., Tom Cruise). “That’s the best I’ve ever seen Cruise,” Depp offers, approvingly, of the actor’s role as Les Grossman. I ask if Cruise’s portrayal reminds Depp of any Hollywood executives. “All of them,” he says. And when we aren’t watching the TV, silent Lon Chaney movies run unattended.

Knowing his affinity for the stars of earlier eras, I ask him if there is any Hollywood icon he still hopes to spend time with. “I already met her,” he snaps. “Elizabeth Taylor.” One day actor Roddy McDowall, who knew that Depp was rather awestruck by Taylor, called him and said, “Do you want to come to dinner?” Depp attended and found Taylor to be “the best old-school dame I’ve ever met. A regular, wonderful person. Billy Bob Thornton and Steve Martin were also there. Boy, did I take to her. For dinner she ordered liver and onions and just smothered them with salt. I admired that. She’s an astonishingly great broad.”

By day, the Vajoliroja can feel like a floating book club. Depp (who is a habitue of L.A.’s Dragon Books and Houle Rare Books) spends the week practically memorizing The Rum Diary, word for word—both the novel and the script. Wyatt reads Hunter’s Hell’s Angels and a history of rare French wines. Deuters is onto Balzac’s The Girl with Golden Eyes. Holmes is finishing Bryce Courtenay’s The Potato Factory, and I’m onto Louise Erdrich’s latest.

And whenever Depp gets bored or can’t sleep, he paints—specializing in oil portraits. “When I can focus on something like guitar or painting, I do,” he says. “I started painting people I admire, like Kerouac, Bob Dylan, Nelson Algren, Marlon Brando, Patti Smith, my girl, my kids. I painted Hunter a couple of times. Keith Richards. What I love to do is paint people’s faces, y’know, their eyes. Because you want to find that emotion, see what’s going on behind their eyes.”

As we leave Bahamian waters for the open sea, the waves start to swell, changing from lapis to peacoat blue. In an instant, our noble isolation takes on an edge of dread. A lone cargo ship can be seen on the distant horizon. Whales appear from time to time, spouting off. Other than that, the yacht is all we’ve got. Even with our G.P.S., if we were to capsize, we would all be goners.

Nonetheless, conditions are pretty good for sailing: two feet of sea sway with a three-or four-foot swell. And we realize that, if we were to run into real trouble, we could always divert to the Turks and Caicos, where Keith Richards has a home.

At sea Depp wears a blue-and-white-striped Rasta-man cap to hold back his hair. His frayed T-shirt has cigarette burns—souvenirs of a wayward youth. This is his last chance to indulge in genuine scruff before facing the movie cameras. Throughout the passage, Depp is in his element, pleased to be waterborne, choppy or not.

After a few glorious days on the water, we approach San Juan harbor. There is no better way, I posit, to arrive in a Caribbean port city than to be flying the Jolly Roger. Especially as we crawl past Paul Allen’s Octopus—among the world’s largest privately owned yachts. Because we’re entering U.S. territory, three Homeland Security officers—all friendly— come aboard. “Everybody in Puerto Rico is excited you’re here,” the lone female officer tells Depp. “They’re busy cleaning up the marina for you.” While this is certainly a fine compliment, it means the paparazzi are sure to descend like swallows.

All at once, I get that sinking feeling. Our escapist fantasy has abruptly come to an end. “I feel like I just traveled the seven seas with Sinbad,” Nathan Holmes chimes in. “Let’s not tell them we’ve been in the lap of luxury. Just talk about our rope burns.”

That evening we all head for a farewell dinner with The Rum Diary director Bruce Robinson and his posse. The son of Serge Gainsbourg, Lulu—a student at Boston’s Berklee College of Music—also joins us. Depp leads a table toast, calling for a successful shoot in honor of Thompson. “Here’s to Hunter, here’s to rum,” Depp says, claiming he’ll do anything for the Gonzo cause—props and all. “I’ll even wear man boobs.”

The next morning, an hour before I depart for my flight home, Depp has a fitting send-off. It is 10 A.M., but he sees no reason for us all not to share a bottle of ’89 Haut-Brion. Depp does the decanting. We all raise glasses to our great escape, which is now but a fading daydream.

“The time has come,” Depp says, polishing off his last glass before the grind begins. “The time has come to start channeling Hunter.”

Having given a quietus to the morning, Depp gets up and makes hand gestures exactly like the great Gonzo. “Oh, my God,” he says, looking at his watch. “Got to shower and get ready for the set.”

In a flash, I’m in a cab, heading for the airport. I’m relaxed, refreshed, and slightly aglow with Bordeaux. And I keep on hearing a soft refrain: