The panel traces itineraries of enslavement and contestation across the Greater Caribbean in the eighteenth and nineteenth centuries. It aims to connect and compare enslaved persons’ experiences of movement and spatial politics across entangled, but also significantly different, spaces - from eighteenth-century Colombia to nineteenth-century Spanish Florida, Jamaica and Cuba. It considers the maritime trading routes and transport technologies that framed such experiences and the political practices that arose from this entangled slave-trading. It also follows both “paths of enslavement” and “ways of freedom” deep inland, across land-based transport infrastructures connecting plantations and other rural terrains to the complex, shifting social geographies of expanding port cities, with their new carceral spaces and forms of spatial resistance. In so doing, this panel seeks to highlight how the coerced movements and contestatory mobilities that shaped the Greater Caribbean were most apparent at the granular level.