Research on entanglements of power inquires into the multiple positions from which power of domination and resistance are exercised across time-spaces. This paper discusses the dominating efforts of colonizers (Europeans, Yucatecans, Mexicans and US-Americans) to territorialize the Mexican Caribbean in order to anchor it to global patterns of accumulation. The hegemonic power to grid, survey and discipline a region that for a long time was conceived as “empty space” becomes entangled with the resistance power exerted by indigenous Maya and local ecosystems. These entanglements of power have converged in contemporary Akumal to produce a geometry of spatial segregation in which Mestizo and Maya workers are segregated by government and businesses from spaces designated for tourist use. My findings show that spatial inequality has been constructed along a pattern of increasing globalization, local reconfigurations of local power positions, and the trans-nationalization of space. In Akumal this pattern could only be imposed by reinterpreting space, through tourism, from the logic of a resource to be exploited, to the logic of a good to be preserved and enjoyed in-situ. Local resistances to this hegemonic pattern have managed to delay and sometimes bend some of its spatial outcomes. The latest of these bends led to the creation of Akumal Pueblo. An analysis of the detailed genealogy of this bending reveals that a great source of resistance power to alter hegemonic spatial outcomes resides in human agents whose identities were formed autonomously, that is, squarely outside the region’s entanglements of power, but who have chosen to re-signify them in order to fully embed themselves within these entanglements.