This short two-week immersive course moves beyond the sun, beach and sand modalities of experiencing the Caribbean and instead helps students develop an interdisciplinary understanding of the culture, history and socio-political factors that have given rise to this dynamic region. Special attention is given to moving beyond a linguistically singular and myopic vision of the Caribbean, to one that emphasizes its complexities and contradictions through a comparative lens. While we will explore the various routes of cultural formation, we will also explore the social institutions that shaped the region and the processes of socialization and indigenization that took root. Students will gain keen insights into the importance of the Caribbean in the creation of the modern colonial world, and the forging of anti-colonial resistance to Empire. As such, attention will be given to the resistive/oppositional practices that countered the dominance of the plantation which later shaped the region’s cultural diversity and varied articulations of freedom in the aftermath of slavery.