This paper lays the ground for a novel discussion on the encounter between José Martí and Antonio Gramsci. It argues that Martí and Gramsci can be profitably and innovatively read together when interrogating the profound “spatial articulations” that animate their political vision. The discussion principally focuses on Martí's concept of Our America and Gramsci's Southern Question. Methodologically, the article deploys a “diachronic tactic” that mobilises a broad body of literature that emerged long after Martí's and Gramsci's lives, particularly considering contributions within Radical Geography and Postcolonial Studies.