U.S. law states, “U.S. travel service providers, such as travel agents and tour operators, who handle travel arrangements to, from, or within Cuba must hold special authorizations from the U.S. Treasury Department to engage in such activities.”
OFAC licenses companies as authorized Travel Service Providers (TSPs), who are legally entitled to make commercial travel arrangements to Cuba. TSPs can only make reservations for individual travel for licensed travelers. You must obtain approval before proceeding with a reservation. (OFAC may issue TSP licenses to certain companies and organizations permitting them to offer pre-packaged group tours, so long as such programs fall within the areas for licensed travel.)
However, referring to non-TSP travel agencies and tour operators, “It is possible to provide travel services to U.S. persons legally able to travel to Cuba for family visits, professional research, or news gathering,” says Michael Krinsky, a partner in the law firm of Rabinowitz, Boudin, Standard, Krinsky and Lieberman (740 Broadway, New York, NY 10003, tel. 212/254-1111, fax 212/674-4614, www.rbskl.com/mk.html [1]), which represents the Cuban government in the United States. They may also be able to provide services, such as travel arrangements to Jamaica, from where a traveler makes his or her own arrangements for travel to and within Cuba. Treasury Department regulations do not “show a clear penalty against travel agents who book travel this way.” Travel agents should double-check the regulations, however, with OFAC or with Krinsky.
Links:
[1] http://www.rbskl.com/mk.html