As a master metaphor, the island has been a fecund source of inspiration across many domains. From More’s Utopia to Darwin’s evolutionary theory to Ungers’s archipelago, insights derived from “island thinking” are commonly extrapolated across diverse scales and fields. The appeal of the island metaphor lies in its capacity to simplify the complex and frame the apparently unbounded. Yet the concept seems to contradict current mainstream thought and practice in geographic and design fields. The globalization motifs of openness and interconnectedness, and ecology’s privilege of environmental processes and flows over forms and boundaries, both challenge the pertinence of the island as a cognitive device for territorial description and intervention.