A trip across the Straits of Florida into Fidel's forbidden zone is smooth sailing—except for the waves and rapacious customs officials
Michael Binabib

The irony was as deep as the Straits of Florida. On the same day that Juan Miguel González arrived in the United States to pick up his son Elian, my friends and I were setting sail for Havana from Key West. We weren't leaving home in search of anything as significant as freedom or opportunity. We were just four guys temporarily fleeing the free-market battleground of our homeland. And as that goes, the timing is never right.

"I shouldn't be taking this trip right now," said Jim, an importer-exporter from New York's Upper East Side, as he came aboard. "I really can't come either," added Elias, an antique-map dealer from Miami. But his son, Michael, a professional photographer and captain of our 38-foot sailboat, had been turning down lucrative jobs for weeks in anticipation of our sail. "Are we actually doing this?" he asked incredulously as we pushed off.

Michael had done all the legwork to make the trip legal. (In order to return to the States without a hitch, we would join the Hemingway International Nautical Club at the Cuban marina where we were to dock. It sponsors regattas from Fort Lauderdale, Key West, and Tampa, "hosting" U.S. sailors so they don't break the embargo by spending greenbacks.) Now, as the familiar landscape of Burger Kings and Texacos disappeared behind us, Michael made one last call from the helm. "If you don't hear from us in three days," he told his brother in Manhattan, "call the Coast Guard." Not long after that we sailed into international waters, and his cell phone cut out for good.

Of the 200,000 Americans who visited Cuba last year, it's estimated that at least 1,000 arrived by boat. In yachts and sloops, large and small (but no smaller than the government-required 26 feet), they set off from ports around the world. "Brother, don't let anybody tell you there isn't plenty of water between Havana and Key West," Ernest Hemingway wrote in To Have and Have Not. I could see what he meant. Six hours into our 20-hour sail, the sun dropped, the skies clouded, and lightning forked the southern horizon. With five-foot swells, a queasiness set in among the crew. It was dark and lonely out there, and we didn't know who or what we'd find--whales, sharks, rafts, unlit vessels, maybe even pirates.

What we got instead was weather. The wind changed, the rain hit, and the waves mounted. Our tiny ship was bounced enough to keep us all awake. On an unprotected stretch of ocean 600 feet deep, you don't drop anchor when it's time for bed; you keep sailing. From dusk to dawn, with his GPS keeping us on course, Michael remained the vigilant captain. In the galley, Jim, an experienced sailor, fought seasickness. Elias was thrown from his bunk. Sleepless in the bow, I imagined we were being punished for daring to cross international waters to a forbidden country; and for being soft-bellied capitalists, too.

After 10 stormy hours, the waters calmed and Michael sighted the first buoy, 12 miles from our destination, Marina Hemingway. He attached a Cuban flag to the mast to let authorities know that we weren't coming to make trouble. Cuban coastguardsmen waved us by.

When we docked for inspection, our first formal greeting came from an elderly, tawny-skinned quarantine doctor in a lab coat. He stepped aboard and shook our hands firmly, saying in Spanish, "Welcome to Cuba." He checked our eyes for signs of hepatitis and asked if there was any chicken on the boat, but seemed far more intent on other things. "These are delicious," he remarked, referring to the dried California apricots we'd been advised by other visitors to set out, along with cold sodas and beer. Between bites, Dr. Quarantine turned to Elias, the Spanish-speaker of our group. "If you're going to tip me, it would be best to do it now."

Next came two inspectors from Immigration. While looking at our passports and filling out forms, one helped himself to a soda and took another for later. "She'll have a beer," he said of his colleague, a laughing woman whose wrists were stacked with bracelets. They spoke in halting English, but warmly. "You're welcome in Havana," the man said. Before they left, I offered each of them a Pokémon toy for their kids. They took several. (There's a quarantine on U.S. chicken in Cuba, but none on Pokémon--yet.) A dog named Maggy sniffed around and left paw prints all over, but knew enough to leave the snacks alone. On and on the inspections continued, with all the speed of a laborious holiday dinner. We went through several dozen cans of soda and beer, and many baseball caps. Two customs officials reeking of cologne took it upon themselves to empty a package of cookies onto a plate while filling out forms. "You are welcome in Cuba," the last inspector repeated. "Everyone will treat you well."

He was right. Marina Hemingway was efficiently run, and the staff was gracious (perhaps beyond gracious; a security guard offered us muchachas one night). With an average of 100 boats docked there every day, the marina feels like a Fidel-free zone. Built in the pre-Castro fifties and revived for tourism in 1994, it has boat slips, two hotels, a restaurant (Papa's, named for Hemingway), a supermarket, a rental-car office, a bar, and CNN wherever you turn. While there have been occasional reports of theft at the marina, most visitors find Cuba to be a safe country filled with people made gentle by a lack of competition and an excess of unarmed police.

By U.S. law, we were not allowed to eat anything but the food we had on the boat, where we were also required to sleep. But during our six-day visit we took daily jaunts to Havana (15 miles east) or southwest to Viñales. Everywhere we felt as if we'd stepped back in time. Cars and buildings were vintage, dating from 1959 and before. Advertising was scarce. Music--the breed of Latin rhythms that preceded Ricky Martin by decades-- seeped out of every doorway. No dotcoms. No dot-Communists either, from what we could see. Impressed by the quiet dignity of so many people carrying on despite the quagmire of their political situation, we reveled in the sight of old men lazing on ancient bicycles, commuters waving to us from the backs of trucks, farmers plowing tobacco fields with oxen. At the beautifully decaying community center in Viñales, we watched teenagers at an outdoor dance.

Finally, it was time to head for home. As we cruised into international waters, a full moon was rising over Havana, in all its dilapidated glory. Never mind a moon over Miami: it was the most romantic dusk I'd ever witnessed.

With each nautical mile, Cuba was slipping away. After a blissfully calm night we awoke to a sea "as blue as a plate," as the Cubans would say. Soon we spotted the first U.S. buoy, indicating we were almost home. Not long after that, Michael was on his cell phone to New York and Jim was dealing with a business crisis in Brazil. Elias got out his Filofax. I checked my phone messages. We hadn't even touched land, but we were back to work.

Cruising to Cuba
Even if you have no boat of your own, you can still sail to Castro's shores, and legally at that. Beginning in November, Toronto-based Cuba Cruise Co. (800/387-1387 or 416/964-2569; www.cubacruising.com) will offer Americans three- to four-night cruises to Cuba from Nassau, Bahamas, from $535 per person. Passengers are registered as guests of a Canadian nonprofit foundation, thereby classifying them as "humanitarian travelers" (the ship does bring medical and educational supplies to approved Cuban organizations).

Since the law is constantly in flux, call the Cuban Assets Control Regulations bureau of the U.S. Treasury Department (202/622-2480; www.treas.gov/ofac) for the current U.S. regulations before you book.