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This paper examines trade patterns across the Caribbean Community (CARICOM)15 Caribbean economies—and highlights how external connectivity shapes trade integration, resilience, and growth. It makes three main contributions. First, it analyzes goods trade, tourism flows, and cross-border banking linkages within a consistent gravity-model framework. Second, it presents new evidence on the role of physical connectivity—shipping and air transport—in shaping import sourcing patterns and tourism inflows, drawing on granular bilateral trade, tourism, and flight capacity data. Third, it shows that while financial connectivity matters in a global context, it is not the primary binding constraint for Caribbean economies; instead, limited physical connectivity emerges as the more decisive factor shaping trade patterns, diversification, and external vulnerabilities. Overall, the findings underscore how constraints in transport and logistics connectivity can limit economic diversification and resilience in small, open economies. The paper’s findings speak directly to a broader challenge facing small developing states (SDS): how transport and logistics connectivity shape trade integration, resilience, and growth outcomes. While the analysis focuses on the Caribbean, it has direct implications for other regions—including the Asia-Pacific—where geographic fragmentation and connectivity gaps similarly constrain economic diversification and external resilience. Presenting this work at the Annual Meetings in Bangkok would provide an opportunity to connect Caribbean experiences with those of SDS in other regions, and to foster a broader discussion on policies to strengthen regional integration and external connectivity