The routes of Caribbean interactions with Africa during the 1950s and 1960s were several and varied: not only did Africa appear in the literature as forms and interrogations of an ideological homeland, but African and Caribbean writers met on European soil, exchanged ideas in conversations with each other, and became part of literary projects fostered through European universities and publishers. During this period, many writers and scholars from across the Caribbean region moved to the newly independent African countries, and engaged with the cultures in their writing and professional and personal lives. Conversely, many African writers turned to the Caribbean for models of how to engage with the cultures of colonialism and their afterlife. This chapter examines the pilgrimage of identity and diaspora enacted through the African–Caribbean connection, the new literary movements that it generated, as well as the shared project of political and cultural decolonization.