Obtain a license from the Department of the Treasury's "Office of Foreign Assets Control" (OAFC). According to the Department of State, you may be eligible to obtain one of these licenses if you are visiting a close relative, traveling as a journalist or on government business, employed as a research associate, by a telecommunications company on in the medical or agricultural commodities fields. You may also be eligible if you are an undergraduate student, a graduate student or researcher or a religious worker. Call the OAFC's toll free hot line at 1-800-540-6322 for more information.
Pre-arrange for a Cuban citizen or non U.S. national to pay for your accommodation, transportation, food and any other expenses you might occur before you depart if you plan on traveling to Cuba without a license. According to the Department of State, unlicensed U.S. citizens who spend money in Cuba may face civil penalties and/or criminal prosecution if caught. If you are uncertain as to whether or not you'll be able to facilitate such payment but aren't otherwise qualified for a license, you should not travel to Cuba.
Book your flight to Cuba. According to the Department of State, only licensed travelers may book direct flights to Cuba--others must fly through a "third country," such as Mexico or Canada. Contact a travel professional to inquire about the most economical and direct route to Cuba possible in your specific situation.
Make necessary health preparations. As of May 2010, the Cuban government has begun requiring all visitors to hold a non U.S. insurance policy. Officials at the border will sell temporary policies to travelers who lack one, although it's not clear how much these might cost or which services they might entail. Additionally, if you are coming to Cuba on a foreign scholarship, you'll need to obtain an HIV/AIDS screening prior to travel and bring your test record with you.
