Research and policy analyses on island development commonly assume perspectives emphasising characteristics that distinguish island development from development in continental contexts, while drawing upon development theories advanced and honed in continental contexts (Clark 2009). Consequently, island development is widely understood in terms of policy choices conducive to either gentrification (growth, regeneration, reinvestment) or decline (decay, degeneration, disinvestment). We argue that this approach builds on a myth that poses a false choice propagated by and supportive of powerful interests, and suggest there are alternatives to this false choice that involve neither dystopian decline nor the normalised utopia of externally driven investor-oriented development. In so doing, we draw on two bodies of literature: gentrification research that casts light on uneven development and the false choice assumption; and research on commons and commoning that expounds alternatives to the ‘regenerate (read gentrify) or decline’ imperative. Gentrification research relevant to critiquing the false choice between regeneration and decline is first briefly presented, followed by an overview of island gentrification. We then consider commons and commoning as alternatives to this false choice. We finally narrow in on a small set of examples, drawn from island settings, where practices are geared to navigate development between gentrification and decline, highlighting the environmental and social advantages of such developmental pathways.