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If I manage to get a permit from the Licensing Division of the Office of Foreign Assets Control to spend money in Cuba, where can I find a flight or boat to the island?
Excerpted from Cuba Information Manual: The Definitive Guide to Legal and Illegal Travel to Cuba by Michael Bellows.  For details on how to purchase a copy of this book, click on the "Cuba Information Manual" menu item on the Homepage of this website.
U.S. citizens who are traveling to Cuba under the General License provisions or who are granted Specific Licenses by the Licensing Division of the Office of Foreign Assets Control to spend money in Cuba can catch a charter flight to Havana from Miami, New York, or Los Angeles.  To get on one of these planes, you must make arrangements with an OFAC-licensed travel service provider (TSP) or a special interest group that is licensed by OFAC to make such travel arrangements.  Flights depart from Miami International Airport daily.  You will need a visa from the Cuban consulate before you can reserve a seat; the TSPs can help you get one (for a fee—fifty dollars or more).  Visa processing differs for anyone born in Cuba, regardless of one’s current citizenship; ask the TSP about this or contact the Cuban Interest Section in Washington, D.C.  If you don’t make your accommodation arrangements with the TSP that arranges your flight, the TSP—in order to get your visa—will require you to provide them with an address where you will be staying in Cuba.  If you have obtained a Specific License from OFAC or are traveling to Cuba under the General License provisions, you don’t HAVE to board a flight from the U.S.  You can fly, swim or kayak to Cuba from anywhere you prefer. For information on flights to Cuba from other countries, see the table on page 18.
Currently there are no commercial boats that depart directly from the U.S., even if you have a permit to go. 
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