If you are traveling to Cuba for one of the following reasons, you are traveling under a general license that requires no permission. For others, you will need what is known as a specific license from the Department of Treasury. (Phone: (202) 622-2480 or fax: (202) 622-1657). Start calling the Department of Treasury about four weeks after you applied to see how your application is progressing and if you need to supply any additional information:
(a) persons traveling to Cuba, and persons traveling with them who share a common dwelling as a family with them, who are traveling to visit close relatives in Cuba in circumstances that demonstrate extreme humanitarian need (such as terminal illness or severe medical emergency), provided that the authorization may be used only once in any 12 month period cases involving extreme hardship; (note: the term close relative means spouse, child, grandchild, parent, grandparent, great grandparent, uncle, aunt, brother, sister, nephew, niece, first cousin, mother-in-law, father-in-law, brother-in-law, or spouse, widow, or widower of any of the foregoing). If you want to go more than once in a 12 month period, you need to contact OFAC to obtain a license to visit more than once per year.
(b) persons who are Officials of the United States Government or of any foreign government, or of any intergovernmental organization of which the United States is a member, and who are traveling on official business; or
(c) journalists regularly employed in that capacity by a news reporting organization .
If you are traveling to Cuba for one of the following reasons, you need to obtain a specific license (specific licenses are issued on a case-by-case basis) from the Department of Treasury:
(a) individuals who wish to travel to Cuba to do research for a free-lance article. The following documentation must be submitted with the application: a detailed itinerary and a detailed description of the proposed research and a resume or similar document showing a record of publications.
(b) individuals who are traveling in connection with professional research (see sample letter to follow). Persons traveling to Cuba to engage in professional research must engage in a full work schedule in Cuba, and there must be substantial likelihood of public dissemination of the product of their research. No transactions related to tourist or recreational travel within Cuba are authorized in connection with professional research, except those that are consistent with a full schedule of research activities. Persons are considered to be engaging in professional research if (i) they are full-time professionals who travel to Cuba to do research in their professional areas and their research is specifically related to Cuba, or if (ii) they are acting on behalf of an organization with an established interest in international relations to collect information related to Cuba.
(c) individuals who are traveling to Cuba for clearly defined educational activities such as attendance at a meeting or conference held in Cuba by a person with an established interest in the subject of the meeting or conference (i) provided that the meeting or conference is organized by an international institution or association that regularly sponsors meetings or conferences in other countries; (ii) the purpose of the meeting is not the promotion of tourism in Cuba or other commercial activities involving Cuba that are inconsistent with this part; and (iii) activities are related to study for an undergraduate or graduate degree sponsored by a college or university located in the United States.
(d) individuals who, for reasons involving extreme humanitarian need, seek to travel to visit close relatives in Cuba of such persons more than once in a calendar year.
(e) individuals who are traveling to Cuba for humanitarian reasons based on a compelling need to travel, for religious activities, for activities of recognized human rights organizations investigating human rights violations, or for purposes related to the exportation, importation, or transmission of informational materials.
For up to date information, Google: OFAC Cuba