Regional integration is both necessary and problematic. This study used the case of the Caribbean Community (CARICOM) to illustrate the complexities of regionalization in the contemporary era. This region was chosen given its uniqueness as a micro region in the developing world. The central hypothesis of the study is that the realities in the new economic and political order are pushing CARICOM toward deeper integration. Yet, despite the external incentives to integrate, the adversarial political culture within member states is slowing down the pace of integration. This qualitative study combined the historical, case study and comparative methodologies to interrogate the problem. The theoretical guide for the study combines the New Regionalism Theory, which distinguishes between regional integration in the developed and developing worlds and inter-governmentalism, which focuses on the implications of domestic politics on regional integration. The dissertation draws on the experiences of other regional projects, in particular the European Union, to create a broad framework to understand regional integration praxis. The study concludes that there is a complex interrelationship between globalization, regionalization and democratization. The study also found that in the case of the CARICOM, the emerging regional space is being shaped by the push-pull dynamics of integration. The dissertation offers possible scenarios for the future of the Caribbean integration process and recommendations for the way forward