This article analyzes the temporal and spatial regimes on early modern Caribbean sugar plantations by examining ways in which slaves spent their leisure hours. Drawing from travel narratives, letters, and historical works, it discusses how slaves engaged in activities of their choice, most of which took place at night and were shaped by conditions peculiar to night time. In discussing slaves’ activities during their free time, this study argues that night time on Caribbean plantations created a particular kind of space. First, it created physical spaces that were profoundly different at night than they were by day, which to some extent levelled many of the daytime hierarchies inherent in slave work regimes. Second, time and place on Caribbean plantations merged to create entangled spaces in which the new global order dominated by the Atlantic economy, cultural expressions of that order, and the individual lives of slaves were all present.