In an era when progression is at the fore front of most territories agenda, the Caribbean still seems to be struggling for understanding. This book aims to propose the hindrance imposed upon regionalism's progress within the Caribbean. A nationalistic approach was taken to capture the lack of regional integration, against the establishment of the Caribbean Single Market and Economy (CSME). Additionally, free movement and the connotations behind recent data surrounding barriers set between Barbados and Jamaica illustrates the disparities between the institutional processes versus the practical implementation of cross regional movement. This area of focus captures any connected implications, and highlights the progress made among other states whose restricted movement of individuals once existed. Arguably the barriers which exist stem more so from a societal shift which has enhanced the mental borders of autonomy, and it is time for the Caribbean to embrace the benefits of a comprehensive cohesion as a means to progress regionally.