Jackie's CIA boss, Allen Dulles, has given her a new assignment: under cover as a tourist, she will go to Havana, Cuba and ascertain the intentions of a young revolutionary opposed to the dictatorial regime of Fulgencio Batista. His name is Fidel Castro.
During the course of her investigation, she encounters a dashing congressman, John F. Kennedy, but their first meeting ends in disaster. Soon Jackie is being harassed by the Stasi (East Germany's Secret Police), dancing alongside Frank Sinatra in steamy Cuban nightclubs, and fighting for her life. In addition, she's beginning to have feelings for her co-agent - and is torn between her love for him and her burgeoning feelings for the handsome congressman at home.