Inspired by Édouard Glissant’s and Marta Aponte Alsina’s critical-creative work, this book explores how Puerto Rico’s affective archive of Caribbean relations, from the nineteenth century through the twenty-first, has envisioned and embodied decolonization and sovereignty in relation to the archipelagic, the sea, and Caribbean regionalism. The book’s transdisciplinary archive includes historical figures and their legacies; political and activist thought, textuality, and action as performative interventions; and performance and live arts pieces, objects, materialities, and texts as political/activist actions. Affect, Archive, Archipelago begins by delving into the historical-political figures of Ramón Emeterio Betances, Luisa Capetillo, and Pedro Albizu Campos. It then encounters the work of the live arts collective Agua, Sol y Sereno; the political/activist work of Amigxs del MAR, Comuna Caribe, Mujeres que Abrazan la Mar, and Coalición 8M; and Teresa Hernández’s transdisciplinary artistic trajectory. Finally, stemming from the book’s argument and the immediate historical-political-affective context of Puerto Rico’s summer 2019 rebellion (Verano Boricua), the book offers some reflections and proposals for furthering decolonial, sovereign, archipelagic, and reparatory horizons for Puerto Rico