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During the past twelve months, Shaw has made more than a dozen trips to the "large island 90 miles south of here," as he coyly refers to Cuba in flyers that periodically surface around the waterfront at the Key West Bight Marina.
Shaw peddles his Cuba excursions as weeklong fishing charters and sightseeing expeditions around the western Caribbean, and he believes they are legal. Still, in an uncharacteristic display of restraint, he avoids using the C-word in print.
This is a nod toward the U.S. embargo, which prohibits people under U.S. jurisdiction from engaging in "travel-related transactions" within Cuba. Maximum penalties for violating the 1917 Trading with the Enemy Act are ten years in prison and a $250,000 fine.
For anyone other than journalists or those on official government business, the conventional way around the law is to apply for a license from the U.S. Treasury Department. But the chances of being granted a license are slim. Luckily, Shaw lives in unconventional Key West, a refuge for oddballs and outcasts, rebels and revolutionaries, a city that has made an art out of pioneering creative ways to circumvent federal law.
Throughout the century, Key West boaters have earned a living from smuggling, bootlegging, and gunrunning. U.S. law was nothing more than a navigational inconvenience, and they just sailed around it. Recently this attitude has been applied to the embargo against Cuba. About two years ago boaters discovered that as long as they claimed to have refrained from spending any money on the island, they could travel back and forth without fear of federal prosecution. It's that simple, say the increasing numbers of sailors who are making the run.
It's also that cheap. Depending on the type of charter and the number of days, a trip to Havana will set you back $200 to $500. If the fare is too steep, you can always sign up to work as a crew member in exchange for a discount. To find a boat that's Cuba-bound, just ask the dock masters at the various marinas throughout the Keys, though your luck will increase the farther south you go.
"We're planning on leaving around 10:00 a.m. so that we'll clear Cuban Customs by noon the next day," Shaw explains, his voice crackly and hoarse over the phone line after being roused on his digital beeper. "You're going to love Cuba! The people just fall all over themselves to help you. We'll spend two nights in Marina Hemingway and then go west along the coast to Cayo Paraiso. The whole time I'll be trolling. You've never seen so many fish. It's called Cayo Paraiso because it's like paradise! Dolphin, grouper, marlin, lobster. You're going to eat the best meals in your life."
For Shaw the allure is virgin fishing grounds. For others it's the music, the pretty women, the cheap booze. Some even cite Cuban family values. Whatever their reasons, more and more boaters from all over Florida are sailing for Cuba, anchors aweigh and the embargo be damned.
"In the last nine months, travel to Havana seems to have doubled, tripled even," says Martha Campbell, assistant dock master at the Key West Bight Marina, the city's largest. "It's just that they always wanted to go and they're not afraid any more." While the less brazen boaters will sneak out of the harbor and then slink back without alerting U.S. Customs, others announce their return and invite federal inspectors and immigration officials onboard.
This is not as reckless as it might sound. True, some boats are searched for Cuban souvenirs such as rum and cigars, which are confiscated if found. But in the absence of evidence to the contrary -- a hotel receipt or a restaurant bill -- boaters recounting even the most improbable feats of frugality are taken at their word.
Customs officials who enforce the law explain that they have no choice but to rely on the honor system, though they realize it is a malleable concept for free-wheeling, party-loving boat captains who find no honor in abiding by nitpicking regulations. "It's like taxes. If somebody is going to lie to you, then they are going to lie," says a philosophical Michael Sheehan, spokesman for U.S. Customs in South Florida. "Our system of justice in the United States all goes back to a certain acceptance of honesty."
Sue Woolley, U.S. Customs port director in Key West, estimates that between one and four boats arrive in Key West from Cuba each week. According to figures kept by the U.S. Immigration and Naturalization Service, in the last fiscal year, 163 boats acknowledged having sailed from Cuba to Key West, a nearly 300 percent increase since fiscal year 1993, when only 54 boats admitted making the 90-mile voyage. About half of the 1993 boats traveled with the Basta! flotillas, a series of ventures into humanitarian aid that resulted in the first legally sanctioned Key West-Cuba crossing by American ships in decades.