Historians have often assumed that the development and dissemination of a clarified geography of the afterlife was central to late medieval eschatological preoccupations, albeit that they have differed on a central question, the causes and chronology of Purgatory’s emergence as a space. This essay reconsiders that geography and pays special attention to Purgatory, but it focuses on continued disagreement about its nature, with questions persisting about where purgatorial punishment happened, where purgatory (or purgatories) might be, and what the places of pain looked like to the eye of visionaries. The essay also explores how these different conceptualizations were able to co-exist in late medieval imaginations, noting that Protestant divines identified in this diversity a weakness of Catholic teaching about the fate of the dead, drawing attention not only to the unscriptural origins of Purgatory but also to the varied and sometimes contradictory stories retailed about just what and where it was.