Focusing on the navigational trajectories of sea captains and sailors who, between the 1780s and the 1810s, connected New Granada’s ports with other Caribbean and Atlantic ports, this chapter argues that the circulation of people and information made possible the emergence and consolidation of a transimperial Greater Caribbean geographic space. Sea captains and the crews they commanded were the creators of this transimperial region. Their circulation and the information they spread resulted in the creation of a regional space that challenges preconceived notions about the existence of isolated Spanish, British, and French imperial spheres. The chapter is organized in two sections. The first one examines the trajectories of seamen who connected New Granada’s Caribbean coasts with Spanish and non-Spanish territories in the Caribbean and the Atlantic world. Focusing on two specific types of sailors—captains of Spanish merchant vessels engaged in interimperial trade and ordinary sailors working on board insurgent corsairs—this section stresses the mechanisms of information transmission to show how social interactions resulted in the creation of a region that historians can use as a coherent unit of historical analysis. The second section attempts a characterization of the region sailors created that puts the sea at the center of historical analysis and reflects on the possibility of thinking the transimperial Greater Caribbean as an amorphously demarcated aqueous territory.