The pursuit of nissology, or island studies, calls for a re-centering of focus from mainland to island, away from the discourse of conquest of mainlanders, giving voice and platform for the expression of island narratives. Yet, studying islands ‘on their own terms’, in spite of its predilection for “authenticity”, is fraught with epistemological and methodological difficulties. The insider/outsider distinction does not work all that well when it comes to islands, where hybridity is the norm. This paper seeks to extend this debate, grappling especially with the contributions of Grant McCall and Peter Hay to the sparse literature. Five dilemmas related to indigenous island geographies are presented and discussed, in a semi-autobiographical style.