ABSTRACT European sixteenth-century cartography, narrative descriptions of the islands, and Spanish navigational manuals provide a framework to understand the Caribbean region as a geopolitical stronghold of European rivalries and antagonistic propaganda for European imperial and pre-imperial powers. The first part of the essay focuses on Spanish Peninsular cosmographers and sailors – such as Alonso de Santa Cruz, Juan López de Velasco, Juan Escalante de Mendoza, and Baltasar Vellerino de Villalobos – to reexamine how the notions of maritime predation in the Americas influenced their depictions of the islands and, by extension, that of the Indies. The second part of the essay centers on the works of non-Spanish Peninsular cartographical representations of the Caribbean zone – such as those of Giovanni Battista Boazio and Gerardus Mercator – to reassess the role of maritime predation in contemporary depictions and identify contra cartographies that disputed the Spanish Crown’s territorial order and projected areas for potential economic profit.