The characterisation, legal status and future of islands are increasingly prominent in international and legal affairs. This emerging ‘legal era of islands’ demands a clearer understanding of the multiple distinctive legal issues that islands, whether as sub-national political units or as the territory of continental or mainland States, raise. This article conducts the first contemporary study of these issues by examining the international and constitutional legal status of island territories. It finds that although the relationship between islands and mainland States is characterised by incredible diversity, island territories are pursuing a range of innovative strategies to preserve and protect their autonomy.