This special issue is concerned with how smallness, proximity and connections have shaped, and still shape, the history of the Lesser Antilles in the Eastern Caribbean from European colonisation in the fifteenth century onwards. The relatively small size of the Lesser Antillean islands, and their close proximity to one another, set in motion exchange and connections between communities. Smallness and overexploitation through export crop agriculture, however, also exposed islanders to resource scarcity. Indeed, with European colonialism came lifeways that were decidedly unsustainable, both in the short term and also, in a certain sense, in the very long term. Thus, for centuries, islanders living on small islands, in close proximity and with a limited resource base, have turned towards their neighbours across the sea. They have crossed formal and informal borders to carve out places for themselves and their loved ones. It is this long history of islanders living on small islands, often marked by exploitative economic systems, which is the theme of this special issue.