Island development trajectories are heavily impacted by their relevance, similarity, complementarity and value in relation to continental development pathways. I would argue that this is so, also because of the physical proximity of islands to their respective metropolis, making the former island units in and of their respective mainland. This paper proposes a politics of distance. It examines how physical detachment from the mainland (and from central government) impacts on an island's ability to determine its own destiny and developmental course. This paper does so by reviewing how near islands and remote islands have: (a) nurtured different levels of jurisdictional status and autonomy; and (b) used that jurisdictional resource, where available, to chart their own development trajectory, in ways that may be similar, complementary, different and outright in opposition to mainland ambitions and plans. In such liaisons, remote islands are more likely to avoid the clutches, overtures and demands of (more distant) powers-and thus depart from mainland agendas-than near islands.