The thesis is concerned with assessing the scale and importance of the interaction between Scotland and the West Indies in the later part of the eighteenth century. In analysing the symbiotic relationship between a metropolitan region and a colonial sphere, this study seeks to further the on-going reappraisal of British imperial activity. Within the West Indies, the thesis focuses particularly on Jamaica and on the Windward Islands, which were ceded to Britain in 1763. For Scots, the new opportunities in the Windwards were especially attractive. In this period, Scots formed a significant, and disproportionately large, part of the white population and tended to conduct their affairs in networks based on ties of kinship or local association. These were essentially transatlantic, and were often based on pre-existing networks which were extended from Scotland to include Great Britain and its Atlantic empire. In addition to facilitating all aspects of the Scottish-West Indian interaction, the networks helped to forge new, concentric identities within a imperial framework. The thesis considers this transoceanic interaction by examining a number of key themes. The two opening chapters discuss the Scottish and Caribbean contexts in which the thematic chapters. The first of these is concerned with the structure of Scottish affairs on the plantations, and the next examines the role of Scots in medical practice. Two further chapters assess the political implications of the Scottish presence, one in a West Indian context, the other from a British imperial perspective. Chapter seven reviews Scottish mercantile activity. The final chapter looks at the nature and direction of the repatriation of people and capital from the Caribbean to Scotland.