This paper constitutes a multi-layered feminist analysis of the intertwining of migration and gender in the Commonwealth Caribbean. The analysis reveals that embedded within the Caribbean imaginary is the functioning of this region simultaneously as a heavily trafficked, global way station and a diasporic, desired destination. The paper dissects the nexus of gender and migration to expose how the concept of the social relations of gender has itself migrated and travelled through historical and contemporary migration studies. These narratives themselves become gendered, and for significant periods in the repeating, anthropological, sociological and political economic surveys, gender is mistakenly perceived as disappearing and emerging, relevant and irrelevant in understanding the mass movements of women and men into, out of and across this space we know geographically as Caribbean. This mapping of the conceptual terrain of the migrations of gender demonstrates that relations of gender acquire new manifestations in different phases of Caribbean migration, yet these do not obscure the old, enduring hierarchies of inequalities of power that are mapped onto the politicised, sexualised, bodies of women and men. The analysis argues that the concept of gender is as nomadic as the women and men whose lives are shaped by unequal gender relations. It wanders from the continents of Africa, Asia and Europe to permutate and perpetuate inequalities of gender in the forever repeating Caribbean diasporas.