The paper addresses the narrative that qualifies micro and remote islands as lands of freedom, suggesting that they can also be lands of despotism. Philosophers from Plato to Aristotle, to Thomas More, to Montesquieu and Rousseau have claimed that micro polities, preferably insular, represent the ideal society, where everyone is actively engaged in public affairs and pursues common good. Literature has represented islands as lands of freedom, opportunity, challenge, success, adventure, redemption, away from the corruption of Europe. However, in the nineteenth century a new narrative has emerged in fiction, which abandons this idyllic approach: islands as lands of despotism. Islands are interpreted as lawless lands, characterised by rivalries between individuals. Moving from these contrasting suggestions from literature and philosophy, the paper discusses the constitutional arrangements of Commonwealth Caribbean and Pacific micro states, in order to investigate where they stand with respect to the dialectic freedom/despotism.