Those aren’t urban legends you hear about Americans who hop a direct flight from Canada or Mexico to Havana, only to be hit with an eye-popping fine in the thousands of dollars after they return. There are federal laws against making a trip to Cuba solely for tourism, and the government takes them very seriously.
The reasons the anti-travel restrictions to Cuba even exist are as complex as overall U.S. relations with the country over the last 50 years. In theory, Americans are prohibited from going there because the dollars you spend would aid the Cuban economy and indirectly strengthen its communist government. Yet these types of limitations don’t exist between the U.S. and any other country in the world. If you want to travel to Iran, Burma, North Korea, or anywhere else, you’re free to do so, as long as you receive a visa from the host country.
That’s not to say that you can’t go to Cuba for other reasons. Journalists on assignment, academics performing research, government employees on official business, members of humanitarian and religious missions, and people who have immediate relatives in the country can apply for and receive licenses to travel there by the Treasury Department. And in the past year, the federal government has begun granting a trickle of “people-to-people” licenses, which were issued in the late 1990s but halted under President George W. Bush. The U.S. State Department outlines all of the rules and policies on travel to Cuba here. Miami-based Cuba Travel Services will point you in the right direction for applying for a license and help you plan your trip. I'll explain the two main ways you can get there after the jump.