Before the 1960s, Cuba was a traveler's paradise and its casinos, luxury hotels and sandy beaches were dotted with U.S. tourists. But since the Cuban revolution, U.S. citizens have endured travel restrictions to Cuba. The reasons for the current restrictions, now part of the longest embargo in U.S. history, remain primarily political.
After conflict erupted in March 1958 between the Batista government and Cuban rebels led by Fidel Castro, the United States placed an arms embargo on Cuba. As the U.S. government moved to punish Castro's forces with a 1960 reduction in the Cuban import quota of sugar, the Soviet Union stepped in and bought millions of tons of sugar. By the start of the decade, this Caribbean stage of the Cold War was set. With Cuba's proximity to U.S. shores, the U.S. government's problems with Cuba's new government would clearly not be taken lightly.
In light of the relationship forming between the Soviets and the Cubans, President John Kennedy's broadened trade restrictions by executive order on Feb. 7, 1962. He then introduced the first travel restrictions the next year on Feb. 8, soon after the Cuban Missile Crisis. Later that year, the Trading with the Enemy Act froze Cuban assets within the United States and further outlined previously placed restrictions, known as the Cuban Assets Control Regulations.
The travel restrictions placed on U.S. citizens needed to be renewed every six months, and each administration upheld the regulation until President Jimmy Carter, who did not renew. Instead, he went on to remove the regulation against spending U.S. dollars in Cuba. Just a few years later, in April of 1982, President Ronald Reagan put the regulation back into force. In June of 2004, the Cuban Assets Control Regulations were modified so that they do not actually forbid U.S. citizens traveling to Cuba. Instead, they disallowed any transactions to be made by U.S. citizens in Cuba. President Obama further adjusted the regulation.
Obama loosened the travel ban on April 13, 2009, to allow for all Cuban-Americans to travel freely between the two nations. While the previous regulation required even Cuban-Americans to apply for a permit from the Office of Foreign Assets Control--a very difficult process that only allowed for travel in the case of family illness or emergency--Cuban-Americans can now enter Cuba without the lengthy process. For other U.S. citizens, the travel ban still holds.
From the beginning, the large Cuban communities of vital Electoral College states such as Florida and New York have been largely pro-embargo and therefore politicians have continued to uphold the travel ban. Also, as Obama outlined in 2009, the United States is waiting on Cuba to demonstrate to the world its desire to open its society before the trade and travel restrictions can be fully removed. Obama explained that this must include a release of political prisoners, ending government fees taken out of money sent from abroad (especially from Cuban-American relatives living in the United States and letting U.S. telecommunications companies enter Cuba.
Under the current Cuban Assets Control Regulations, American citizens (besides those authorized to travel as explained above) cannot spend money in Cuba and therefore cannot realistically visit legally. But many U.S. travelers enter Cuba from a third country such as Mexico or Canada and simply ask to receive no stamp upon entry. After your visit, you would also have to depart the same way.