The main areas of Picturesque Travel during the second half of the long eighteenth century were the Lake District, Wales, Scotland and the Isle of Wight; of these locations the Isle of Wight has been the least reviewed. This study examines Island-centred historical and topographical material published 1750-1840 in conjunction with journals and diaries kept by contemporary visitors. The available archive is examined within a framework of the developing aesthetic theories of the period that surrounded the picturesque and rise of antiquarian interests, supported by more recently proposed systems of analysis. The systems and practices of viewing the Island are considered. Foremost here are the kinds of hierarchies used by the topographers in their descriptions; were they based on man made constructions, landscape qualities or status of the individual? Further to this, the study examines the ways in which contemporary diary and travel notes inform us of the Island and conclusions that can be drawn of the attractions and alterities that the Island presented to such a wide and varied group of people. Viewing, Recording and Consumption are common threads that run throughout this discourse. The Island is identified as a location of alterity; which provided alternative social conditions for visitors and residents from the mainland. The rural cottages, villas and mansions, built as retreats during this period are considered within this context. This study, which is not exhaustive, will begin to correct the recent neglect of academic interest and show that the Island could have a higher profile within eighteenth century cultural studies.