This essay explores the role that conversations about race and racism played in forming a partnership between an African American public relations firm and the Cuban National Tourist Institute (INIT) in 1960, just one year after Fidel Castro’s victory over Fulgencio Batista. The article highlights how Cuban revolutionary leaders, Afro-Cubans, and African Americans exploited temporary transnational relationships to fight local battles. Claiming that the Cuban Revolution had eliminated racial discrimination, INIT invited world champion boxer Joe Louis and 50 other African Americans to the island in January 1960 to experience “first class treatment — as first class citizens.” This move benefited Cuban revolutionary leaders by encouraging new tourism as the number of mainstream white American travelers to the island declined. The business venture also allowed African Americans to compare racial violence in the US South to the supposed integrated racial paradise in Cuba and foreshadowed future visits by black radicals, including NAACP leader Robert F. Williams. The politics expressed by Cuban newspapers and travel brochures, however, did not always fit with the lived experiences of Afro-Cubans. This essay uncovers how Afro-Cubans threatened national discourses by invoking revolutionary promises to denounce continued racial segregation in the very facilities promoted to African American tourists. Ultimately, ideas about race did not just cross borders between Cuba and the United States in 1960. Rather, they constituted and constructed those borders as Afro-Cubans used government claims to reposition themselves within the new revolutionary state.