Vamos a Cuba!

Join us as we try to hitch a ride to the island before the gold rush strikes.

Nobody gets in a little boat to go from Miami to Cuba and live by their own free will in tyranny and oppression. — Rudy Giuliani, in an interview with Larry King following the 2000 repatriation of Elián González


You pictured Miami as all white linen suits and rum-filled coconuts.

It was fun at first. Weird and strange. But you've come to see it's like everywhere else in America: You drink thin yellow beer and eat fried, fatty food. You have your car insurance. And your dental insurance.

Emily Flake
Emily Flake
Emily Flake
Emily Flake

You can't keep track of your cell phone or your camera or your iPod. You worry, daily, about losing them. Do you even really want them?

There are forces at work, out to get you. Your boss. And terrorists. And identity thieves. Parking tickets have created a terrible pit in your stomach. Or is that cancer?

America, you realize, is hazardous to your health. Miami is going to slowly and painfully kill you. So why not make your way to the closest alternative: sunny Cuba?

You won't have anything to worry about down there. There's no such thing as insurance. Kids drink state-sponsored rum. If you play your cards right, you might nab a slow, lazy job as a crooked bureaucrat — perhaps even a white-suit-wearing one.

In the long term, it might not be a bad opportunity: Fidel is no longer in charge. Who knows? Maybe you could help pave the way for Uncle Sam's 90-mile Havana Highway to the McCuban Resort & Casino. It's like California during the gold rush! But instead of striking it rich, you'll strike it ... steady.

It's just a matter of getting there.


Although the Cold War ended for most of us when the Berlin Wall came down almost 20 years ago, it rages on between Washington and Havana. The people of Cuba are considered our enemies. Giving them money — even hanging out with them — is illegal.

JFK restricted our travel and spending in Cuba during the 1962 missile crisis. Carter let the limitations lapse in the Seventies; Reagan brought them back in the Eighties. During the Clinton years, illegal charter flights departed from the Magic City nine times a week, according to the Miami Herald; Havana-bound tourists numbered close to 100,000 annually.

Resolutions to lift the ban have perished in every Congress since 1999. They do not gel with the executive agenda, especially since President Bush got the message that Miami's conservative Cubans weren't gonna wave the wand on his 2004 re-election bid unless he tightened the screws.

Their precious ban had become a local laughing stock. Americans who received threats from the U.S. Treasury Department's Office of Foreign Assets Control demanded hearings; the Treasury had no judges to hear their grievances, so nothing happened.

Thus the Texas airman third class came to town and made a speech constructively painting Castro as a pimp. He even quoted El Jefe as advertising Cuba's hookers as the "cleanest and most educated prostitutes in the world." He further suggested Castro had turned the entire island into a pedophilic playground in order to fuel "his corrupt regime."

By election time, Dubya had installed a bunch of judges to preside over administrative hearings for people who had been too dumb and/or honest to lie about their trips to Cuba. You know, the cigar-chewing rubes who blabbed to customs agents about how proud they were to be back in a country where they were free to do as they pleased.

These fools were presumed guilty and forced to pay through the nose. Going to Cuba without Uncle Sam's say-so can incur fines up to $250,000 or 10 years in prison.

Which is why I wanted to go to Cuba. If someone was going to turn me upside down and shake me by the ankles until all of my constitutional rights come tumbling to the floor, I'd like that person to at least be wearing a green uniform and carrying some kind of assault rifle.

Rumor had it that Key West's wild men still cruised to Cuba all the time. All I'd need to do was hitch a ride. Once at Hemingway Marina in Cuba, I'd simply thumb it a few miles into Havana. In the true spirit of banana socialism, I hoped to get everything for nothing.

It was settled. No ride would be refused. No money spent. Take that, Office of Foreign Assets Control.


In the middle of a late January day, I stuck out my thumb for a little more than an hour in front of the Freedom Tower, our famed memorial to Cuban immigration. As dark clouds formed overhead and cold winds blasted my shins with construction grit, scores of huge, empty cars stampeded by. They were the biggest cars on Earth, no doubt, driven by the least generous people. Maybe it's all the murder that made Miamiams look the other way, but it hurt. It just made me want to escape even more.

So I broke my rules right away and rode the Metrorail to the end of the line. From the Dadeland South station, I was rescued by a Colombian pizza delivery man in a wheezing Honda addled with Jesus bumper stickers. For about 20 blocks, he pined for Nebraska, where phone bills and property were cheap and he didn't have to wake up at 5 a.m. to deliver the Herald.

He let me out, with a blessing, in Palmetto Bay.

A battered black Chevy Astro van with tinted windows stopped in the middle of traffic right there on South Dixie Highway. A young woman named Kathy beckoned, and I hopped into a red-carpeted cabin packed with home-schooled children.

The kids pleaded with me not to go to Cuba. They knew I'd certainly die. Their neighbor had told them his whole family had been taken away and slaughtered by the Cubans. This talk wasn't helping my resolve, so I asked to see their religious comic books and we talked about Hebrew instead.

Kathy said she'd happily take me all the way to Key West if I could spot her gas money. I thanked her anyway — there were rules, after all — and stuck my thumb out at the south end of the Miami-Dade County line.

It wasn't long before I was sucked up by Todd, a self-described New Jersey redneck. He drove a massive, well-appointed Chevy pickup, and squirmed, hacked, and cursed all the while — another terminal victim of the American Dream. His back was wrecked from being rear-ended by a bulldozer while he was working a construction job in Pennsylvania. He smoked and coughed constantly, drawing wads of phlegm up from the bottom of his lungs.

"Are you a cop?" he asked before dipping into a cup holder full of blackened marijuana roaches, which he sucked in like medicine.

As the roads narrowed and delivered us from scrubby pines to long bridges surrounded by bright turquoise waters, Todd became only more anxious and ornery. He hated the Keys. "Ain't shit out here to do but drink," he said.

He dreamed, somewhat, of the Caribbean islands, where he had vacationed at all-inclusive resorts. Todd had even skirted Cuba on a fishing boat. "But we turned right back," he said. "We knew they'd blow us out of the water with a cannon if we got too close." He looked forward to the day when he could stay in a deluxe Cuban resort.

When Todd learned of my plan, his crooked jaw went limp. He called a fishing captain friend and asked him if it was even possible. "You might as well be going to Beirut," Todd cried after getting the no-go from his pal.

Though we both agreed I wouldn't find any all-inclusive resorts in Cuba that would take me in for free, he allowed it might not be all cannons. Todd determined the best possible route to the island would be aboard the yacht of some fun-loving Canadian millionairess. "I love my girlfriend and my kids," he said. "But I'm still holding out for that beautiful rich chick with a yacht."

He dropped me off three miles from Key West, and I set off walking into the sunset.

"Either you've been misled, or I've been misled," he conceded, before peeling off to go get drunk.


A brief visit to the Key West Yacht Club proved fruitless. No Canadian flags in sight. A gala made up of stern-looking white folks in navy blue blazers and evening gowns buzzed under bright clubhouse lights that poured out into the night, illuminating a big sign. Members Only, it warned.

A yachtie in clogs advised me that no one at the club went to Cuba anymore. He adjusted his spectacles and glowered at me as I crossed the street to the Veterans of Foreign Wars Post 3911. Inside, sloshed old soldiers lined up at the bar. Their bygone platoon names billboarded on stiff mesh caps, the vets offered two-dollar Yuenglings (thanks, Uncle Sam) and free advice.

A profane ex-Naval gunner with a thick Chicago accent objected to the Cuba plan through his snow-white mustache. "It's just a shitty little island like all the rest of 'em," he surmised. But if I really wanted to go, he said, I should simply enlist and ask to be stationed at Guantánamo Bay. "That's a free ticket to Cuba right there."

As I drank my way farther into town, it seemed everyone knew how to get me to Cuba — for between $1,000 and $2,000. But that just wouldn't have been communist.

Key West revealed itself as a noxious sieve, where strapping American youths dissipated into the soft cottony drunkenness that pervades the island's daily life. Beyond a certain age, every man's head had devolved into one of two things: Hemingway gourds — well-lined, ruddy, and white-haired — or rotted pumpkins — shriveled, red-orange, and stinking of piss and smoke and booze.

But the town loved the idea of going to Cuba. Why not? Everyone else in the hemisphere is doing it. Few expressed any fear in toodling around Castro country. Unlike the exiles in Miami, Key West's wayward scoundrels aren't waiting for Fidel to die before they start puttering south. They're waiting for the abdication of King George.

During a pleasant evening stroll around a local cemetery, I came upon an inebriated realtor walking his dogs from a bicycle. He told me he'd been to the island twice. The first trip was a "licensed humanitarian dealie"; the second happened when he and a few drunk friends "just kept going." He found Cuba to be the most beautiful country on Earth.

"On the way back, we spotted a group of rafters," he grinned. "We radioed Brothers to the Rescue and gave them their location. But, frankly, being four gay men, we just sort of wanted to keep them." He added that he and his crew simply docked his boat the following day and walked home, never checking in with the U.S. Customs house.

A local fishing charter captain and his first mate had both found wives in Havana and brought them back. So had a newspaper photographer, whose wife now drove him totally fucking crazy. He bought a couple of acres in the Cuban countryside for about $600 and plans to settle down as soon as cars and air conditioning become readily available.

An off-duty Key West cop denied ever going himself but vouched that the ocean continues to be wide open. He advised me, over Guinness, to duck through the Bahamas.

A city commissioner told me I'd need at least 2,000 euros to get to and from the island. As we chatted in the courtyard of his Duval Street strip club complex, he dropped tips on how to avoid eyeballs and keep my nose clean in Cuba. He knew I'd never get there, though, not by hitching. Not in this wind.

Fear and cynicism plagued the happy populace. People believed they were being spied on by their own government and that their property might well be seized for making George W. Bush look bad at the Versailles coffee counter.


Eddy sat with his feet kicked up on the cash register of the most lascivious sex shop on the planet.

Built roughly like a high school sophomore, the middle-age man had smoothly plastered his black hair over a sizable bald spot. His little cheeks drooped down at the sides of his face and stretched, often, into a boyish grin. His loud party shirt opened to the middle of his stomach, revealing a wealth of gold chains and chest hair. Eddy looked like the kind of guy who might hit on your girlfriend at a bus station.

Behind him a galaxy of cock rings, lubes, whips, and beads (for your asshole) hung from hooks on the wall. Butt plugs the size of garden gnomes stood in a row, like sentinels, on a shelf below his feet.

Eddy said he's working on the paperwork to bring his true love over from Cuba. "She's gotta stay with me for two years, as I understand it," he said. "Hell, I'd be a happy son of a bitch if she stayed two years."

He boats to Cuba, but only in the summertime. "If a cold front comes through," he said, "you could end up with 10-foot swells out on the ocean, and then you're trapped down there for a week."

During the winter, Eddy flies to the island. Which is a pain, because he first has to drive all the way to the "Miami fucking airport." Eddy hates Miami and associates it with only bad things.

Sometimes he jets into Havana through Costa Rica, where he enjoys cheap, pretty young women as well. "They don't hassle you as much," he said. "But everything in Costa Rica costs twice as much."

Cuba can cost big too. In response to Bush's new policy, Eddy said, Castro now forces Americans to change their dollars to pesos for an exorbitant fee. Moreover, everyone you meet there tries to steal from you. Eddy imagines he would steal whatever he could too.

While he ruminated on the economics of being an international pervert, tired, unshaven men wandered in to purchase tickets to the store's numerous jerk-off booths in the rear. Eddy, ever the pleasant shopkeep, obliged them all with smiles and kind words.

He never moved from his position at the counter, a fact he thoroughly prided himself on. Even the arrival of his miserable grandpa of a boss, Bob, didn't seem to irk Eddy at all.

Bob, a retired jeweler from up North who got into the adult-store business out of boredom, was dressed in typical bland snowbird fashion. Unlike Eddy, he took little joy in life. "Key West," he grumbled, "I can take it or leave it."

Bob, too, had been to Cuba — under Batista. "It was a giant whorehouse," he recalled. "You could get anything you wanted."

He pleaded with Eddy to stay away from Cuba and stick to the "señoriters" in "Cahsta Ricka."

Eddy could not. "I miss my sweet little girl," he said flatly.

Bob fumed. "She's a whore, bitch, conniving whore."

Eddy smiled, unfazed. "Everybody's entitled to his opinion."


The next afternoon, I eyed the Garrison Bight Marina, just across Overseas Highway from the VFW. Charter fishing boats pull out in the mornings and return in the afternoons to hang huge grouper on a row of hooks. A world-weary attendant at an information booth on Duval Street had insisted someone at the marina would be crazy enough to take me to Cuba.

Nothing stirred in the quiet along the docks. The sound of opening beer cans drew me to the back of a sizable fishing boat, the H2O Bilge Management, cluttered with a miniature Zen garden, a bicycle, and a potted rosemary bush.

Standing on the deck of the mighty vessel stood Papa Hemingway himself, pouring Silver Bullets into a humongous coffee mug and squinting out into the early afternoon. He said his name was Ed Gully and he was pissed he couldn't take me to Cuba.

"Another one of our freedoms gone down the tubes because of bullshit politicians," he muttered.

Gully had been part of a notorious 2003 race to the island that led to the ruination of a pair of local lives. "You go and see Michele Geslin," he advised.

Geslin and her husband, Peter Goldsmith, had become legendary on the island after federal agents dragged them out of their beds and indicted them on criminal charges for running a regatta between Key West and Cuba.

Since then, they moved their sail shop from downtown Key West up to Stock Island. So I abandoned Key West and made way for their shop. I arrived to discover a two-story warehouse. Its walls were lined with reams of colored synthetic materials. Breezes poured through cracked windows, and tunes sounded from a small radio.

"Michelle's not in," called a voice in a soft Southern-hippie drawl. "Why don't you sit a spell?"

John sat cross-legged and silver-haired on the floor, cutting material for a huge blue spinnaker. He said every two or three days someone eager to get to Cuba comes through the shop with a broken sail.

John retired about 10 years ago as an engineer at Ford. "Every industry I've worked in has been outsourced," he said, tossing the sail onto an old Singer sewing machine and stepping on the foot pedal. "Shit, all the materials you see on the wall are flown in from elsewhere. Boy, we buy everything from communist China. The only thing this country manufactures anymore is debt and bullshit."

The retiree still has friends — mostly Frenchmen and Canadians — who go to Cuba. "A 30-foot sailboat with a fiberglass hull is still pretty hard to pick up on radar," he said. "But if they put that eye in the sky on you, then you're fucked.

"If they want to get you," he added gravely, "they'll get you."

John doubted I'd get a ride. "It's like the Sixties around here, again, son," he laughed. "You don't know who's ridin' on your boat — you might be a damn government snitch for all I know."

He was interrupted by the arrival of Geslin. Standing a little more than five feet, snowy haired and clad in a red sweater, she looked like she could be featured smiling on a biscuit tin. She spoke sweetly and seemed to have come to a place where she could finally laugh about her ordeal.

But not too hard.

She and her husband had run a regatta to Cuba since 1996 as a fully funded group hosted by the Havana Yacht Club. The race took about a week, alternating between days of sailing and partying. The Cubans were even allowed to take their boats out past the border buoys and sail alongside the racers. Geslin made sure her hosts always won.

Upon their return from the 2003 race, their boats were searched by OFAC agents aided by dogs and local police. They confiscated maps, cameras, and trinkets. "Anything that looked like it had to do with Cuba," Geslin recalls. The following morning, armed officers dragged the couple out of bed (Geslin was in pajamas) and booked them on charges of conspiracy and trading with the enemy. In November 2004, a federal judge in Miami threw out the criminal case but didn't close the door on civil fines.

Indeed the Department of the Treasury has hounded them like a junkie relative.

"They wanted $11,000," Geslin said. "Then they wanted $6,000. I just got a letter last week demanding funds."

Geslin handed me a free T-shirt and gave me a hug goodbye. The blousy white tee read "Conch Republic Cup 2003" below an American sailboat drifting into the Hemingway Marina.

She couldn't help me get to Cuba.

After making a few phone calls to a couple of wayward Frenchmen, John threw his hands up as well. "People hate having someone along that doesn't know shit about sailing," he said.


All signs pointed to Stock Island's tragic shrimping community, a poor population locally associated with crack-smoking. No one really thought catching a ride with a shrimper would be a good idea, but time and money were running out. If they couldn't take me, no one could — and I would resign myself to living in Miami.

As I made my way past trailers and abandoned furniture, weird glares and long leers followed me down the road. A battered red Ford Escort veered onto the swale in front of me. The passenger side mirror had been smashed off, and the windshield wipers were broken.

A tire and a nurse's jacket occupied the back seat. A muscular 35-year-old man with odd scars on his cheeks sat drunk behind the wheel. His name was Joel, he wore nothing but blue swim trunks, and he told me to get in the car.

I climbed in and explained the Cuba plan. He flew into a tizzy.

"Come on, man!" he pleaded. "What did you do? It can't be that bad, man! I've gone to jail, man. It can't be that bad."

When I told Joel about the white suits, he insisted I accompany him to his house full of booze.

"You're an American," shouted Joel, cranking up AC/DC as the car swerved onto the road. "Stay an American."

At his palm-lined duplex, Joel began pouring tall glasses of rum dabbed, ever so slightly, with drops of Coca-Cola.

"You don't want to go to Cuba," he continued. "Look at it this way: You do a crime in America, you get locked up, it sucks. You do a crime in Cuba ... see what happens. Especially to us Americans. Castro hates you. If his boys catch you, they'll fucking murder you!"

Joel's mother was French, and his father killed himself when Joel was a boy. He got several DWIs in Concord, New Hampshire, and a judge urged him to leave for good. After finding his wife in bed with another guy, he decided to move to Key West, arriving seven years ago on a Greyhound bus with $650 in his pocket.

Joel claimed to work only a few days a week tending bar. Today was his day off.

"If I had to guess," he said, smoking and smirking, "it was a higher power that made me pick you up today." Plus, nobody likes to drink alone.

He suggested I make up a resumé — writing wasn't really good for anything — and hunker down in Key West.

Joel poured more rum into a pair of plastic cups and asked me to take a walk into the fuzzy, orange afternoon.

Families strolled happily through the brilliant sunshine toward a long concrete pier that jutted out into the crashing waves. Joel took pictures of a Japanese family, demanding they say "Key West" before he snapped the shot.

The pier stretched out into an infinite horizon of whitecaps, alight in the early flames of a fantastic sunset. Joel plopped himself down on the edge, careful not to spill his drink, and pulled his dick through one leg of his swim trunks.

"That's the way to Cuba," he sang, pissing into the ocean. "Swim, motherfucker! Swim!"

I sat down next to him and looked out at the horizon.

"If there's a country that dominates, don't you want to be on that side?" Joel asked, playing Socrates. "I know part of you doesn't. But don't you? We're a power country. We have every brain. We're a country of mixed wits.

"If you go to Cuba, you idiot, you're going to die," Joel concluded gravely. "You're going to fucking die. We got a whole embargo on that country. They all hate us. We don't fuck with Cuba. We don't buy Cuban coffee; we buy Colombian coffee and fuckin' Arab ... er, Arabia coffee. We buy that shit...."

Joel's wisdom and rum filled me with a patriotic fervor. He was right! My bad-ass government knows best.

We finished our drinks and raised our empty plastic cups toward the sherbet-colored heavens: To our irascible Uncle Sam — so wise and powerful he can arbitrarily decide where we go and how we get there.

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