Determine if you qualify to travel to Cuba. General licenses are only granted to certain travelers. Some qualifying categories include but are not limited to those visiting a close relative, journalists, government officials conducting official business or those whose professional travel is non-commercial or academic in nature.
If you do not qualify for a general license, you might be eligible for a specific license. These are granted for those who are visiting non-Cuban nationals, and those affiliated with educational or religious institutions. Some specific licenses are granted on a case-by-case basis, for instance those working with humanitarian projects, freelance journalists or public performers. Enquire if you qualify for travel at the official website of the U.S. State Department.
Apply for your specific license through the U.S. Treasury Department. Send a letter outlining your travel plans and any supporting documentation required to prove your eligibility for a specific license to: Licensing Division, Office of Foreign Assets Control; U.S. Department of the Treasury; 1500 Pennsylvania Ave. NW; Washington, DC 20220.
Obtain a passport and a visa. Despite being licensed either with a general license or a specific license, the Cuban government requires this additional paperwork for an American to legally travel to Cuba. Any attempt to enter Cuba illegally could result in stiff jail sentences. Be aware that Cuban citizens and foreign visitors are subject to both physical and electronic surveillance and there is a strong military and police presence on the island.
Obtain non-U.S. medical insurance. As of 2010, Cuba requires that visitors must have non-U.S. medical insurance, and will provide temporary policies to those who do not have it. HIV/AIDS entry restrictions may exist, and while Cuba does not force travelers to take these tests, foreign students on scholarships are required to produce results of HIV/AIDS tests. These can be conducted by U.S. labs.
Secure the airfare to Cuba. Flights from the United States to Cuba are prohibited, but certain airline charters fly directly from Miami to Cuba. The majority of flights going into Cuba are charter flights like ABC Charters, which is licensed by the Office of Foreign Assets Control of the U.S. Department of Treasury.
Passengers from San Jose may also elect to fly out of Canada or Mexico on Cuba's national airline, Cubana de Aviación. Early reservations are recommended, as these flights tend to be oversold. Re-confirm your reservation at least 72 hours prior to your flight.
