The Caribbean has figured prominently in narratives of security, mobility, and transnational connections. Referred to as the “Third Border” in US foreign policies, and inhabiting contradictory geopolitical spaces between North and South America, the region also negotiates narratives of in-betweenness and in/security in relation to more “leisurely” pursuits, notably, tourism. By revisting Stephanie Black’s critically acclaimed documentary film Life and Debt and retheorizing the concept of critical conversations, this essay analyses the ways representations of in/security have framed media images and policy discourses of Caribbean tourism. This retheorization contributes to the development of interdisciplinary international debates on tourism promotion, inequality, and policy decision making. While geopolitics and tourism studies have largely tended to remain distinct areas of research, this particular film—and related conversations—illustrate the urgent need to exhume the interdependency of both. Antonio Benítez-Rojo’s concept of “repeating islands” is drawn on to illustrate the ways reexamining representations of Caribbean tourism and geopolitics as part of a series of interconnected and multilayered conversations opens up new possibilities for interrogating how tourism narratives have reinforced, produced, and stifled opportunities for diverse, secure, creative, and inclusive social spaces.

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