The actual personality and character of islands as liminal spaces, at once local and global, at once national and cosmopolitan, may depend significantly on the dynamics of their port (and often capital) cities. By looking at what happens in the spaces of potential cultural exchange and brokerage in such locales—including working waterfronts, markets and commercial transactions, coastal tourism establishments and activities, religious rituals and celebrations—one gets a better sense of whether and how islands, in spite (or because) of their smallness, can be ripe for human conviviality, multilingualism, tolerance and a peace based on prosperity. In contrast, it is when island societies develop a narrow, exceptionalist and special definition of themselves—including pillarised notions of their own, internal island communities in terms of race, ethnicity and nationhood—and become convulsed by questions of identity, that they reduce their appeal as ‘welcoming societies’ and instead become the strategic bulwarks, flanks and edges of hard borders.