This article challenges several of the firmly held convictions drawn from extant research on return migration to the Caribbean. For many contemporary small island societies undergoing rapid change and transformation, modernization and integration into the wider global economy, today's younger and more youthful return migrants are no longer an ineffective demographic cohort. Despite their numerically small size, many are demonstrating they can be influential “agents of change.” No longer merely returning retirees, they are more diverse, in terms of age, life‐course transitions, class and gendered social positions, family networks, and migration histories. Multiple identities are the rule, rather than the exception, as returnees of different ages choose to live, work (and play) in island society, to give something back to the island home of their parents or of their youth. Many embrace transnational strategies to live in and between two worlds, or more if their family network's reach is multilocal.