This paper critically examines the possibilities of education for social transformation (EST) in the context of the Caribbean Community (CARICOM). This is a region with a history of colonialism and embodies some of the central dilemmas of globalization, such as inequality and environmental precarity. Thus, conceptually, EST holds great promise for social justice and environmental sustainability. The paper argues, however, that EST can be relevant to the region only if it takes account of the enduring deep-seated legacy of asymmetries of power, exploitation and inequality in the broader society and within the education system resulting from colonialism and now exacerbated by globalization's processes. Using postcolonial theory as the analytical frame, the paper highlights these challenges to EST in the context of the Caribbean and also identifies educational principles for EST to be a catalyst for social transformation in the region.