Something about the apparent romanticism of islands prompts creative reflections such as those comprising visual artworks in the Dis-covery exhibition touring Australia for 2 years from 2011. The exhibition forms the basis for this paper, written by its progenitor and curator—an artist, and its essayist—a cultural geographer. The curatorial premise was that islands and island cultures are at risk from global and multinational forces, as well as from amplified local impacts internal to the limits of their boundaries. In turn, the exhibition’s aim was to trouble the layered cultural cliche´s that represent island conditions especially in terms of the romantic. Participating artists—all of whom have lived on islands—were invited to explore how islands and romanticism are both containers for disparate yet overlapping ideas, among them references to imagination, projected desire, unsatisfied longing, rising tides, exoticism, resource mining, militarism and marginalization. Drawing on conversations with the artists, and on their writings and works, this paper captures insightful reflections about islands, arts and the geopolitical imagination; reveals significant artistic interventions into the geopolitical spaces of islands; and underscores the productive relations that derive from critical and creative engagements between geography and art.