Apply for a general license with the Department of the Treasury if you are an official government traveler, regularly employed journalist, full-time professional with job-related need to travel to Cuba or if you are visiting a close relative with extreme humanitarian need. If you fall within these categories, you can spend money for travel within Cuba without getting a specific license.
Apply to the Office of Foreign Assets Control (OFAC) to obtain a specific license to spend money in Cuba; it will take about three months to get approved or denied, so apply in advance. Specific licenses may be issued for educational programs, religious organizations, humanitarian projects, freelance journalism, professional research or participation in a public performance or competition.
Write a letter to explain the reason for your visit and why you feel your visit would qualify you for a specific license to travel and spend money in Cuba. Be as thorough as possible to increase the chances of your application being accepted.
Send your application letter and any documentation to support the reason for your travels to the Licensing Division, Office of Foreign Assets Control, U.S. Department of the Treasury, 1500 Pennsylvania Ave, NW, Washington, DC 20220.
Obtain a valid passport and visa in order to gain entry into Cuba.
Make your flight reservations with a third country, such as Canada, Mexico or a European country. Although U.S. citizens may travel to Cuba, there are no flights that connect passengers from the United States to Cuba.
Purchase a non-U.S. medical insurance policy to cover you for the length of the trip; Cuba will sell a temporary policy to those who don't have insurance. According to the Bureau of Consular Affairs, Cuban officials made this a requirement effective May 2010.
Carry the results of a recent HIV test with you during your visit to Cuba. There are some entry restrictions for foreign visitors with HIV or AIDS.
