Vamos a Cuba!

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

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.

Emily Flake
Emily Flake

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.

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