Port Arthur Historic Site is a World Heritage Property in Tasmania, Australia. Inscribed as one of a suite of sites for the role it played in the British-Australian system of convict transportation, management and reform, it is today a major tourist attraction. Like most tourism destinations of the twenty-first century, image capture has become an integral component of visitor experience. Although at first it would seem that Port Arthur oozes images, there are particular locations, themes and views that reverberate through time and space. Reflecting on the theme of repetition, this visual essay seeks to elucidate how the paradox at the heart of Port Arthur’s representation might be used as a creative force or channel for the construction of new kinds of landscape encounter. Using a process of digital photomontage/collage, the essay explores the proposition that creative practice may play a role in activating and re-presenting heritage landscapes.