Essentially, sustainable urbanization is a political choice. Following this proposition, this paper seeks to critically assess the policy-institutional framework that is established or being proposed to shape the urban agenda in the Caribbean. Locating the research activity within a sample of countries in the region, desk analysis of the policies and legislation corresponding to urbanization in these countries is undertaken, complemented by lesson-drawing from case studies of international experience to determine the efficacy of the region’s policy-institutional framework and the extent to which it mirrors international norms. Preliminary findings suggest that sustainable urbanization remains a concept in the Caribbean as policies and legislation either predate ideas of urban sustainability, or do not target sustainability challenges adequately. The paper is part of a larger research project on sustainable urbanization in the Caribbean and therefore is intended to initiate debate and further research towards production of policy relevant information in this area of study.