From the United States
No scheduled commercial flights are permitted between the United States and Cuba.
Licensed Flights: About two dozen companies—called Carrier Service Providers (CSPs)—are authorized to fly direct charters to Cuba from the United States, solely for licensed passengers as permitted by the U.S. Treasury Department. Charters use aircraft operated by Continental, Grupo Taca, and United Airlines. Why are prices so high? One, the monopolistic nature of the CSP business; two, because Cuba imposes landing rights of US$100–133 per passenger. CSPs and licensed TSPs may also make reservations for authorized or fully hosted travelers on flights between third countries and Cuba for authorized travelers.
The following CSPs are recommended:
ABC Charters (1125 SW 27th Ave., Miami, FL 33174, tel. 305/263-6829 or 866/411-1147, fax 305/263-7187, www.abc charters.com) has flights from Miami to Havana (US$559 round-trip) and Holguín.
C&T Charters (932B Ponce de Leon Blvd., Coral Gables, FL 33134, tel. 305/445-3337, www.ctcharters.com) has charters to Havana and Camagúey from both Miami (US$559 round-trip) and New York (US$895 round-trip).
Cuba Travel Services (300 Oceangate, Suite 910, Long Beach, CA 90802, tel. 310/772-2822 or 800/963-2822, www.cubatravelservices.com), with offices in Hialeah and San Juan, offers charter flights from Los Angeles to Havana (US$629 round-trip) and from Miami to Havana (US$449 round-trip).
Marazul Charters (8324 SW 40th St., Miami, FL 33155, tel. 305/559-7114 or 800/993-9667, www.marazulcharters.com) operates charters from Miami to Havana.
Via Third Countries: The Treasury Department issues the following advisory: Except as specifically licensed by OFAC, “The Regulations prohibit all transactions relating to travel-related tourist transactions in Cuba, including prepayment in third countries for Cuba-related expenses” for unlicensed travelers. Nonetheless, thousands of U.S. citizens and residents travel to Cuba through Canada, Mexico, the Caribbean, or Central America aboard foreign airlines.
Anyone showing an airline reservation that includes an onward flight to Cuba will be refused boarding on the flight within the United States. Unlicensed travel therefore requires completely separate reservations and tickets for your travel to/from a third country and to/from Cuba. Since you must make separate reservations for the two legs, you’ll need to pick up your checked bags in your third-country destination then check in again for the Cuba flight (and vice versa on the way home). If possible, pack light and carry everything on to the plane.
Travelers should assume a possibility that passenger manifests for flights to Cuba, including reservations made using the Amadeus reservations system, may be shared with and/or monitored by U.S. authorities.
© Christopher P. Baker from Moon Cuba, 5th Edition