Since the 1960s, the inhabitants of the British Overseas Territory of Bermuda have serially considered and rejected becoming a sovereign nation. This thesis investigates the extent to which the positions taken by politicians and social commentators, who are involved in the debates concerning independence, are informed by their lived experiences and understandings of the island’s past. Grounded in an analysis of the island’s past, this thesis also investigates how Bermudians have historically defined belonging in the political sphere and public spaces according to ‘race’ and class and how this affects the way in which they interact with each other and regard their relationship with the United Kingdom. The study critically engages with postcolonial theory and asks what the existence of this 21st century colony says about the processes of colonialism and post-colonialism. It also considers how this study fits with other research concerning other remaining Overseas Territories to show the value of conducting in-depth studies of specific societies. By surveying archival documents and conducting interviews a fuller understanding of the political and social development of this island is gained, as viewed by colonial administrators, local government officials, and those who publicly challenged the norms that allowed for social and political inequality on the island. These methods are used to engage with questions of how ideas of self and nation were shaped by segregationist formal education and how this was either reinforced or challenged by what was taught around the kitchen table and in the wider society. It explores how Trade Unionist and the fledgling Progressive Labour Party (PLP) saw a move to independence as part of a wider aim to rectify social injustices. The continuity and change in the debate is then reviewed to see how and the extent to which changes both internally and externally interact with narratives of the past to inform how those involved in the debate imagine the island’s future.