US citizens travelling to Cuba, no matter how they get there, must qualify for a “licence to travel”. The stipulations for obtaining a licence have changed several times in the last fifteen years in the ongoing tug-of-war between the US government’s conservative and liberal factions over the provisions and enforcement of the embargo, so it’s always worth checking what the latest rules and definitions are at wtreasury.gov or whavana.usint.gov. In 2011, for example, Washington expanded the possibilities for being granted a licence, allowing more people to travel for educational, cultural and religious purposes.
Currently there are two categories of licence: General and Specific. Confusingly, for a General Licence no application is necessary. If your trip fits into one of the categories which the US Government allows – usually travelling on behalf of an institution for educational, journalistic, diplomatic or religious purposes – then you can travel without having to make an application to the Treasury Department. Individuals travelling independently tend to have to apply for a Specific Licence, which is much more complicated.
The various specialist US tour operators organizing legal tours to the island should be able to assist you in getting your licence and are the most useful sources of information and help.
Travelling without a licence
For US citizens, travelling to Cuba without a licence is illegal, whether you fly direct or via another country. However, some do bypass the legal obstacles by travelling via Canada, Mexico or other countries and buying tourist cards in those destinations to meet Cuban entry requirements, just like citizens of any other country. On request, Cuban authorities will stamp these cards instead of a passport on entering and leaving the island. Most US citizens who travel to Cuba illegally do not bring a stamped tourist card back to the US with them, as this in itself can serve as proof of a visit to Cuba. The penalty for travelling without a licence is a hefty fine and possible prison sentence.