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Due to recent political changes Americans can now travel to Cuba and normal flights have resumed between the U.S and Cuba, but there are some restrictions in place for these visits so U.S travellers should check with their booking agent.
Previously Americans wishing to visit Cuba would fly via a second country Canada, Mexico, Jamaica, or the Bahamas and the Cuban immigration would NOT stamp your passport leaving no record that they had been in Cuba.
Cuba has always welcomed Americans as it was the American government that placed the travel restriction on Cuba and flying under the radar may still be a preferred option for some to escape the restrictions
A 30 day tourist visa must be issued by the airline that you are flying with before your arrival in Cuba. They usually cost between 25 or 30 U.S dollars for a 30 day visa which can be extended for another 30 days at Cuban immigration in Cuba then you must leave the country and then re-enter on a new visa. These Visa runs can be to the Bahamas, Jamaica, Haiti or Mexico.