This article explores young peoples’ perceptions and connections to their local cultural heritage in the Scottish Western and Northern Isles. Typically considered as heritage-rich contexts, this research project sought to gain an experiential understanding of young peoples’ relationship to local cultural heritage assets; in what ways these hold value for them; and if and how they associate these and other aspects of island heritage with their own sense of identity and belonging. Set against the backdrop of increasing youth migration and depopulation in Scotland’s island communities, insights emerged surrounding cultural advocacy, outward-facing representation and, in particular, the impact of tourism – as experienced by young people living in the diverse island contexts of Stornoway, Shetland and Orkney. Drawing on evidence from three island case studies, I present a studio-based approach for creatively engaging young people in heritage focused research. This article has methodological value for practitioners and researchers seeking to amplify youth-led perspectives on cultural heritage, as well as contextual insights in the areas of relational heritage and place-based identity.