You need to write a letter to the U.S. Department of the Treasury requesting a ‘Specific License.’ Only those requesting permission to travel to Cuba for certain professional, humanitarian, or educational purposes will be considered. In the letter, you must provide convincing details outlining the purpose of your trip, including category of travel, description of your research, and documentation of your qualifications. You can download an OFAC-recommended format of the letter from the Treasury Department’s website by clicking on the link listed in the “Resources and Links” page. If you are granted a permit, you will not be allowed to spend more than $185.00 per day in Cuba for land costs (i.e., hotel, dining out, and taxis), $500.00 in transportation costs to and from (not within) Cuba, and you will not be able to bring back any goods or merchandise purchased or otherwise acquired in Cuba. For a period of five years after your trip ends, you must keep a record of all your travel documents and expenditures, and you must furnish these records to OFAC or other law enforcement officials upon demand. A word of warning: The licensing department that receives the applications has a very small staff that receives thousands of requests for permits weekly. It may take months before you get a reply, so give yourself plenty of lead time.
NO APPLICATION FOR A LICENSE TO TRAVEL TO CUBA IS NECESSARY if you can demonstrate that a) you are a full-time journalist on assignment, b) you are a full-time professional conducting research in Cuba, c) you are an official of a U.S. or foreign government traveling on official business, or d) you are attending an international professional conference or meeting taking place in Cuba. Anyone traveling to Cuba under these categories is granted an unwritten “General License” by OFAC that does not require any pre-approval before you leave. But upon your return from Cuba, you will likely receive a letter in the mail from OFAC requesting proof and documentation demonstrating that you indeed fall within the qualifications and guidelines for travel to Cuba under a General License. (continued)
How can I get a permit to spend money in Cuba?