A dividing line, the border is usually perceived in terms of separation and rupture. It is a site of tension par excellence, at the origin of contestations, negotiations, and other conflicting patterns of inclusion/exclusion. This book takes us through an exploration of the border in the Caribbean region, both geographically fragmented and strongly tied through its history, culture and people. This collection of scholarly articles interrogates the border within the specificities of the Caribbean context, its socio-political dynamics and its literary and artistic representations. The transgression of borders and the consequent reconfiguring phenomena are thus applied to the Caribbean and its diasporas, through a transdisciplinary approach. The book combines a multiplicity of research fields, including Social Sciences, Cultural Geography, Geopolitics, Cultural and Literary Studies, hence it offers a global perspective on the topic and transcends disciplinary categories. The contents of the book also stretch beyond geographic and linguistic borders as the contributors come from diverse scholarly backgrounds, affiliations, linguistic areas, and research expertise.