This book analyses the evolving engagement of the United States and Cuba, along with the impact of this relationship on Cuba-CARICOM relations and the Caribbean. Through a Caribbean perspective, the chapters discuss the implications of the U.S.-Cuba relationship economically, institutionally and developmentally. Based on the findings of their research, the authors provide policy recommendations to CARICOM on potential areas for enhancing relations between CARICOM and Cuba, drawing on fieldwork and interviews with policymakers, academics, non-governmental organizations, and regional experts.