Island development is widely understood in terms of policy choices conducive to either gentrification or decline. The authors argues that this approach builds on a myth that poses a false choice propagated by and supportive of powerful interests, and suggests 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, they draws on two bodies of literature: gentrification research that casts light on uneven development and false choice assumption; and research on commons and commoning that expounds alternatives to the 'regenerate or decline' imperative. They also focuses on a small set of examples, drawn from island settings, where practices are geared to navigate development between gentrification and decline, highlighting environmental and social advantages of such developmental pathways. The gentrification of an area is characterised by both a marked upward shift in occupancy in terms of class and socio-economic position, and associated reinvestment in the built environment.