This paper demonstrates how representations of other people and places and the colonial imaginaries upon which they are founded have produced various forms of distance and authority that have justified a variety of Eurocentric interventions. This colonial discourse has been central to the construction of non-western people as legitimate and passive subjects of colonial rule in contradistinction to the active, modern and civilised westerners. But, importantly, these imaginings of the past continue into the present and shape contemporary relations between the ‘west the rest’. However, despite a proliferation of research on the power of colonial imaginations, much less attention has been paid to the contestation of this discourse, particularly by former colonial subjects. This paper, thus, goes on to highlight contemporary forms of agency by those who attempt to challenge and transform colonial representations. For example, people in former colonies are repositioning themselves in relation to the west by appropriating and reworking current manifestations of colonial imaginations. The paper is based on research in small island states in the Indian Ocean. Beginning with the kinds of colonial imaginations constructed through boy´s adventure stories such as Robinson Crusoe, it explores the contemporary neo-colonial expressions that echo these ideas of deserted, idyllic paradise islands and subsequently with how people have exercised agency by instigating processes of negotiation and creative improvisation. The paper concludes that while a colonising legacy pervades present day representations of Third World societies the geographical imaginary of the west can also become an important cultural and economic resource to reposition themselves globally.