The popular Soviet song, “Cuba, My Love,” symbolizes the emotional attachment many Soviets citizens felt for revolutionary Cuba in the early 1960s: “Cuba, my love. Island of crimson dawns. Its song flies over the planet and rings: Cuba, my love!” In one romantically heroic, ideologically appropriate, and mysteriously exotic package, Cuba inspired tired Soviet citizens with its echoes of the Russian revolution, the Spanish Civil War, World War II, and implicitly, Nikita Khrushchev’s own “revolutionary” Thaw. Cuba also promised something new in an era of Cold War competition over the “good life,” namely socialist luxury as emblemized by the sensuous, but now socialist, bikini-clad Cuban woman. This project explores the place of Cuba in the cultural imagination of the Soviet Union, as well as the movement of Soviet and Cuban citizens between the USSR and Cuba as tourists, delegates, and students. It contributes to recent scholarship about relations between the Soviet Union and the Third World, and, secondly, to our understanding of the specificities (or not) of the Soviet sixties, an era for which in both East and West, Fidel Castro’s guerrilla revolution was a foundational moment.