The British West Indies and its sugar industry emerge at the heart of wealth and power by the middle of the eighteenth century. When assessing this devel-opment and analysing how it connected Britain and the Americas there is the tendency to concentrate on those who made fortunes. This has shaped our understanding of the quality of life engendered and nature of the societies that were created on both sides of the Atlantic. Less emphasis is placed on the full range of the experiences of those who migrated temporarily or permanently to the region in the quest for fortune. The people involved included not just large and visible investors such as planters, merchants, bankers, manufacturers and members of government, but as Eric Williams noted in Capitalism and Slavery, members of the middle and working classes. This discussion shifts the focus from the “big planters and merchants” and exposes hidden lives and less visible people who became entangled in an increasingly compilated network, which supported movement from different groups in the society between both sides of the Atlantic world. By focusing on Scotland, with emphasis on the highlands and islands, this paper develops Williams’ contention that sugar and enslavement also affected the lives of “everyday people”. African enslavement made the British West Indies a land of opportunity not just for white planters and merchants, but also for white men from middle and lower-income groups.