The idealised image of the Outer Hebrides includes wind swept beaches, isolated peat covered moors, and craggy mountain cliff tops abounding with wildlife. These images are reproduced in countless tourist postcards and websites to entice visitors to visit, explore, and of course spend their money on the islands. At the same these images create a certain ‘expectation’ of the islands that not only promote a particular ‘way of seeing’ (Berger 1972) the landscape, but perpetuate the dominant narrative of the ‘wild’ wind-swept islands. This visual project challenges these notions of ‘nature’, wilderness and folk heritage by accepting alternative and ‘minor histories’ (Benjamin 1974) of the landscapes. In a subversive nod to the travel postcard, this paper explores contemporary issues of island life and landscape, through unconventional illustrations of island postcards by its residents and the author These postcards are themed around contemporary Hebridean issues, including: isolation, community, landscape, and family. The project contemplates an innovative approach to the illustration, as ethnographer and critical tourist. Therefore, looking at the fragmentary constellation (Gilloch 2002) of images made about the islands that challenges the notion of a ‘wild’ romantic island place, and offering insight into how identity, place and heritage are developed within the region.