This dissertation proposes a comparative approach to Caribbean cultures as a self-defined constellation of diverse artistic and philosophical traditions in dialogue with one another. Through a specific critique of the Cuban discourse around national identity or cubanidad, through the works of local intellectuals and artists –Fernando Ortiz, Alejo Carpentier, Nicolás Guillén, Virgilio Piñera and Tomás G. Alea- this thesis argues that the image of the Caribbean that emerges from these voices, far from being a thematic motif or merely a historical and geographical landscape, is a projection of nationhood which challenges the imaginary boundaries of the island. This revised understanding of cubanidad shares core aspects with the idea of Caribbeanness as a position of enunciation, as illustrated in the works of major Caribbean intellectuals and writers outside the Hispanic milieu. By focusing on the intricate relationship between Cuba and the non-Hispanic insular Caribbean, the main objective of this investigation is to bring a comparative, transregional perspective to the study and criticism of the archipielago as a cultural and philosophical continuum, without rejecting the properly individual value of the national projects and nationalistic expressions.