This article focuses on the cultural dimensions of Sri Lanka's island geography. In particular it argues the importance of regarding the geography of Sri Lankan island-ness as a representational and imaginative trope repetitively and textually inscribed over time. I trace the contours of a topological enclosure that seem so matter-of-fact, natural and characteristic of the Sri Lankan island-state. Inviolability and historical-territorial integrity have become eponymous with the very sign ‘Sri Lanka’, but these ways of imagining and mapping Sri Lankan island space have European, colonial and post-independent spatial histories that are textual and representational. In reading a range of disparate texts that inscribe and map these insular geographies, the essay argues the importance of placing Sri Lanka's island geographies, and its civil war that had the contested island imagination at its core, in a critical postcolonial and spatial historical context. By tracing and loosening some of the misplaced concreteness surrounding settled geographical imaginations and understandings of a Sri Lankan island-state, the essay intervenes in that spatial discourse thereby gesturing toward the political possibilities of thinking and imagining island space differently.