This dissertation focuses on three authors who came of age in the 1980s, Earl Lovelace, Milton Murayama, and Ntozake Shange, reading their novels set respectively on Trinidad, Hawai‘i, and the Sea Islands, as postplantation expressions. My definition of the postplantation builds upon the work of Édouard Glissant, especially “Closed Place, Open Word” where he delineates three phases in literary production from the Plantation: the first is chiefly oral and appears as an “act of survival,” the second is an attempt to justify the Plantation system and is marked by “delusion,” and the third phase is written by descendants of the Plantation in a “passion of memory.” It is this third phase that I call the postplantation. Here, several generations after the system’s collapse, writers return to the plantation as a way to process its legacy. An integral part of this process for the authors studied here is the use of Creole languages developed on the plantation and still spoken today. This dissertation’s specific contribution is to show how the history of the plantation is central to contemporary island discourse. My comparative study of novels about Trinidad, Hawai‘i, and the Sea Islands untangles the effect of the plantation in each of these locations: the legacies of racial and sexual trauma, poverty, and the power structures that continue to replicate the plantation, but also the culture and language that emerged in triumph from this dehumanizing system. My readings of the postplantation illustrate how despite writing about three seemingly very different locales, Lovelace, Murayama, and Shange are engaged in similar efforts to reclaim a local culture, language, and history denied in the plantation’s violent trajectory. The emerging field of island studies, archipelagic approaches to literature, and studies of vernacular in world literature speak to the significance of this doctoral study.