All parts of the Caribbean were shaped by similar forces, including race-based chattel slavery, sugar, capitalism, and the tropical and sometimes deadly natural environment. Within these commonalities, however, is also a great deal of diversity. Large sugar plantations populated by hundreds of enslaved Africans rightfully receive a great deal of attention from archaeologists, historians, and the public. The authors in this volume, however, use innovative techniques and perspectives to reveal the stories of places and times where the rules of this system did not always apply. Collectively, the chapters focus on the spaces in-between, alternate views of plantation landscapes, and the complex dynamics at play in the days following slavery. The authors assess these threads through the analysis of lesser known contexts, such as Dominica, St. Lucia, and the Dominican Republic, and the reexamination of more familiar places, like Jamaica and Barbados. Despite grueling work regimes, and the social and economic restrictions of slavery, people held in bondage carved out places at the margins of plantation societies. In similar fashion, the lives of poor whites, soldiers, and free people of color demonstrate that binary models of black slaves and white planters do not fully encompass the diverse landscape of Caribbean identities before and after Emancipation. The studies in this volume employ innovative research tools to integrate data from a variety of historical and archaeological sources to better understand these alternate stories within and beyond the sprawling sugar estates.