In 1996, the Federal Aviation Administration prohibited civil flight into Cuban airspace without prior authorization. Failure to obey the FAA's prohibition can result in lose of pilot's license, seizure of the airplane and fines. Moreover, if your pilot's license has already been revoked or you are flying without a license, the penalty for entry into Cuban airspace without authorization may include up to three years confinement in a federal prison.
Travel into Cuba via a vacation package paid for in a country other than the United States is illegal. For example, if you book and pay for a cruise in Mexico that includes a day of hiking in Cuba, you will be in violation of U.S. prohibitions against entry into Cuba without first obtaining a license. Penalties include fines up to $100,000 and up to 10 years in federal prison. Additionally, any property you obtain while in Cuba can be forfeited to the U.S. government.
Under U.S. Code, the law allows for increased penalties if you are convicted of willfully circumventing travel restrictions or willfully neglecting to renew a duly issued license for travel to Cuba. Increased penalties not only impose the standard fine of up to $100,000 and a maximum prison term of 10 years, but also, at the discretion of the Secretary of Treasury, you could also be subject to a civil penalty of $55,000 and a criminal penalty of an additional fine of up to $250,000.
