The present study of Guana Island in the British Virgin Islands draws upon archaeological, archival, and architectural evidence to examine the material and spatial aspects of everyday life on the social, geographic, and economic margins of the British Empire between 1717 and 1845. Guana's settlers were yeoman farmers, formerly indentured laborers, and fishermen displaced from other parts of the Caribbean who came to the Virgin Islands for the opportunity to seek their own fortunes in the small island territories initially forsaken by sugar planters as ill-suited for large scale sugar cultivation. Arriving with them, and with increasing frequency over time, were enslaved Africans forced into laboring in the cotton and sugar fields, on fishing boats, and as domestic servants. The present study seeks to better understand how the experience of eighteenth-century Virgin Islanders, both free and enslaved, compared to their counterparts in larger and wealthier Caribbean sugar colonies through a detailed study of households on Guana Island through time. Between the early eighteenth and mid nineteenth centuries, Guana's households underwent substantial transformations in response to the expansion, contraction, and variation of the Virgin Islands' plantation-based economy. Those transformations included measurable changes in settlement patterns, household composition, built environment, and household industry. At the local scale, the archaeological evidence illustrates how colonial processes are frequently tied to the economic use of the land; while at the regional scale, the archaeological evidence highlights the range experiences within the British Caribbean. The evidence presented herein also complicates long-held assumption that Guana's colonial history was limited to the island's occupation by Quakers. Indeed, Guana's eighteenth century settlement occurred earlier, lasted longer, and included a greater number, and wider variety, of people than previously understood.