In 2012, the United States’ Dept. of the Office of Foreign Assets Control (OFAC) introduced the “People to People” educational exchange general license which allows U.S. tour operators to fly groups of American travellers to Cuba.
By 2014, American tourists were travelling to all parts of Cuba–including the remote coastal ports and famous diving locations on the south coast–Jardines de la Reina (Queens Garden).
In 2015/16 OFAC allows American flagged vessels to sail to Cuba for 14 days. There is no longer an application process as the permits previously needed for exporting a vessel that is going to Cuba is no longer required. In addition to the people-to-people general license, OFAC has issued 11 more general license categories for authorized travel.
American boaters should find at least one category that they fit into and therefore qualify for legal travel to Cuba. No paperwork is needed but one must maintain a journal of all activities while in Cuba and this must be retained for 5
years. Tourism is not one of the 12 categories. Since tourism is not permissible, the activities conducted in Cuba must fall within the guidelines of the OFAC categories. American passports are not stamped by Cuban immigration upon
entry.
Today, U.S. Coast Guard cutters that patrol the waters off the Florida Keys are not harassing boat traffic that is headed to or coming from Cuba.