Since the mid-twentieth century, small islands have emerged as important tourist destinations, whether as island-states (Barbados, Fiji), island dependencies (Guadeloupe, Jersey) or state-islands (Okinawa, Cozumel). A longstanding core–periphery narrative holds that small islands are geographically and economically marginal entities fated to spawn homogeneous tourism monocultures within contexts of persistent external dependency. However, further investigation reveals several attendant and pervasive paradoxes which challenge this conventional thinking. This paper outlines these as the juxtaposition of (a) geographic peripherality and experiential core, (b) economic marginality and tourism centrality, (c) tourism monocultures and opportunistic innovation, (d) geopolitical dependency and optimal autonomy and (e) tourism homogeneity and cultural/ecological distinctiveness. A resultant ‘virtuous periphery syndrome’, the product of both necessity and endowment, positions small islands as sites of impressive resilience and innovation capable of providing peak experiences that support robust tourism sectors within contexts of balanced autonomy and cultural distinctiveness. Resolution-based dialectics allow the positive elements of both core and periphery to be identified and combined towards achieving the ideal of enlightened mass tourism.