Any American can go to Cuba you're just not allowed to spend money. The U.S. Department of Treasury considers it trading with the enemy and could put you in prison for 10 years. But according to the U.S.-Cuba Trade and Economic Council, an estimated 174,000 Americans went to Cuba last year. Not all the trips were authorized. Many people try to circumvent the law by arranging prepaid voyages through foreign countries or Internet companies.
Cuba, however, needs tourists and tries to make the return home agreeable. When we cleared customs, we were repeatedly asked if we wanted our passports stamped. If you say no, they won't, so the U.S. government will supposedly be none the wiser.
Since last January, the Clinton Administration has made it easier to legally go to Cuba. People traveling for journalistic, educational, or international business purposes are covered under a general license. Everyone else needs to obtain a license from the Treasury Department's Office of Foreign Assets Control. One way to get a license is by offering to transport humanitarian aid to Cuba such as school supplies and medicine on your vessel. Call John Young of Conchord Cayo Hueso (305/294-0205, firstname.lastname@example.org), who will help you make the arrangements.
Before crossing, our captain, O.B. Pettit, filed a float plan with the U.S. Coast Guard. If you are traveling into "hostile waters," you must file a plan 72 hours prior to departure or the Coasties won't come get you in case of distress. Clearing Cuban customs is easy. The only inconvenience was being forced to seal all handheld cell phones, VHFs, and GPS units in a plastic bag until we left. When leaving Cuba, you can put in a request to the dockmaster to clear customs at any time, which is how we got to leave at 4 a.m. Just be prepared to offer the officials "souvenirs" when you leave.
Stateside, we waited for an hour and a half for customs officials to show up. One officer took us off the boat to fill out paperwork while another gave our boat a cursory inspection. Busting boaters returning from Cuba is not a top priority.
If you fish the Hemingway Tournament, Club Nautico will give you a signed letter stating you were an invited guest of the marina and spent no money during the tournament. Many anglers believe it's their ace in the hole, but this will not necessarily square you with the Treasury Department.
For detailed guidelines on travel to Cuba, contact the U.S. Treasury Office of Foreign Assets Control at 202/622-2480, www.treas.gov/ofac. For excellent Cuban travel information, contact the U.S.-Cuba Trade and Economic Council at 212/246-1444, www.cubatrade.org.