During the early twentieth century, hundreds of thousands of Anglo-Caribbean workers migrated to Spanish-speaking countries, but intellectual exchanges between the region’s anglophone and hispanophone writers remained few and far between. This situation changed above all as a result of the Cuban Revolution, which captured the imagination of a generation of writers and catalysed new networks through institutions like Casa de las Américas. These exchanges would be dominated by concerns with race and sovereignty, while sidestepping questions about Cuban communism and literary censorship. When Andrew Salkey attended the 1968 Cultural Congress in Havana with C. L. R. James and John La Rose, he portrayed Cuba as a symbol of regional anti-imperialism and interrogated the condition of Afro-Cubans, overlooking contemporary censorship scandals. The cross-Caribbean itineraries of Nicolás Guillén and Edward Kamau Brathwaite in the 1970s are emblematic of the cultural diplomacy of the time period. While Guillén’s reception foregrounded his writing on people of African descent and downplayed his commitment to communism, Brathwaite’s poetry was celebrated in Cuba but also subject to suspicion for its black radical content.