Caribbean plantations and the forces that shaped them—slavery, sugar, capitalism, and the tropical, sometimes deadly environment—have been studied extensively. This volume turns the focus to the places and times where the rules of the plantation system did not always apply, including the interstitial spaces that linked enslaved Africans with their neighbors at other plantations. The essays also explore the lives of “poor whites,” Afro-descendant members of military garrisons, and free people of color, demonstrating that binary models of black slaves and white planters do not fully encompass the diversity of identities before and after Emancipation. Employing innovative research tools and integrating data from Dominica, St. Lucia, the Dominican Republic, Jamaica, Barbados, Nevis, Montserrat, and the British Virgin Islands, these essays offer a deeper understanding of the complex world within and beyond the sprawling sugar estates.