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

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.

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