Most travelers to Cuba from the U.S. arrive in the country from Canada, Mexico, Jamaica or the Bahamas. Numerous large airlines travel to Cuba, including Air France, Air Canada and Air Jamaica. Additionally, Cubana de Aviacion, the national airline of Cuba, has flights from surrounding islands, Mexico, Canada and London. When you arrive at your gateway country, you will need to get a Cuba tourist card, which should be filled out before your arrival in Cuba. To complete the card, you'll need to have your passport, return airline ticket and the name of the hotel where you will be staying.
It is difficult to buy airline tickets online to Cuba and only a few travel agencies are licensed to book flights. Online travel services such as Cuba Linda and Cuba Travel USA can assist with booking flights and hotels, but they also must operate with the same restrictions as other travel agencies.
Travelers from the U.S. should make sure they have plenty of cash on hand, as no U.S.-issued credit card or bank card will work in Cuba. According to Lonely Planet, traveler's checks are difficult to cash in Cuba and are "virtually useless" outside of Havana.
In addition to other requirements, the Cuban government insists that all foreign nationals entering Cuba purchase health insurance for the duration of their visit. The insurance costs between $2 and $4 (USD) per day, and can be purchased at kiosks in Cuban airports.
Hotels in Havana are plentiful and range from five-star luxury properties to small pensions and hostels. Other parts of Cuba have hotels, especially along the coast and can be found on various websites such as Lonely Planet, Yahoo Travel, Cubalinda and Cuba Travel USA. It is possible to book a hotel room online, however keep in mind that you may not use a U.S. credit or bank card in Cuba. In many cases it may simply be easier to either work with a travel agency or to book a hotel upon your arrival in the country.
