The Caribbean is one of the most tourism-intense regions of the world with rising levels of over-tourism, especially in dependent small island tourism economies (SITE). More critically, mounting socio-ecological pressures are compounded by increasing climate change and enduring social vulnerabilities, thereby challenging traditional policies and paradigms of growth and sustainability. Drawing on previous studies of inclusive development and community well-being, this research paper frames and extends the phenomenon of over-tourism from a political economic perspective. Based on a historical account of small island tourism development, an in-depth case study of Aruba is presented. Recognized internationally as the ‘One Happy Island’ and one of the most tourism-dependent small island economies, the findings yield a contextualized understanding of the complex and dynamic nature of over-tourism, and identify the main antecedents and effects of over-tourism. The study discusses the evolving economic disconnectedness, environmental decay, social inequality, and institutional failures. The findings describe the role of institutional capture and policy drift which stem primarily from political as well as market forces, and have resulted in a gradual marginalization of community well-being and agency. The paper proposes an extended conceptualization of over-tourism in small island tourism economies by explicitly recognizing that the crux of the over-tourism conundrum in SITE is political in nature and institutional by nurture. Recommendations are provided for transitioning towards community-driven development by building capabilities and pathways for innovation, internalization, and institutionalization in order to strengthen the resilience of small island tourism development.