One of the last territories to be settled by humans, the Juan Fernández islands have long been visualized as an Edenic paradise stalled in time. This article examines how the archipelago has been constructed as an environmental and civilizational frontier, focusing particularly on the role of cruise tourism to Robinson Crusoe Island, which peaked during the interwar period. Cruise tourism, we argue, was central in cementing an image of Juan Fernández as a primitive location, frozen at the point of Alexander Selkirk’s marooning on the island in the eighteenth century. Immortalized in literature by British author Daniel Defoe in the novel Robinson Crusoe, the popularity of the text inspired the establishment of a successful leisure voyage to the islands from Valparaíso, which saw Chileans and foreigners alike engage in discourses surrounding the archipelago as a leisure space which was contingently a key geostrategic part of insular Chile, despite its infrastructural challenges. With reference to the concepts of ‘frontier’ and ‘landscape’ we elucidate how the destination image of a romantic Juan Fernández has been reinforced in the establishment of a tourist destinations of both national and international significance.