This article draws on “regime theory,” particularly on the concepts of cooperation, compatibility of interests, and proclivity to compromise, to examine the rise of the Caribbean Educational Policy Space (CEPS). In making this argument, with the aid of a content analysis of 26 educational policies from the 15 member states of the Caribbean Community (CARICOM), this article first locates the different policy mechanism of external effects, or policy tools, within the regional policy environment that governs and regulates education at the national level to explain how these policy tools and mechanisms have given rise to a very distinctive form of what I call educational regionalism that frames the regional educational policy space in the Caribbean. The data show that CARICOM utilized the noneconomic process of functional cooperation, and the policy tools of lesson drawing, policy externalization, and policy transfer to respond to pressures of globalization across three different policy cycles and concludes by discussing the implications of such a policy maneuver for the integrative project of economic regionalism.