This chapter proposes the socioeconomic metabolism (SEM) and multilevel perspective (MLP) as “novel” conceptual and practical models that island policy makers can apply to analyzing the transitioning from the current island tourism to sustainable island tourism. Pandemics, such as COVID-19 and climate-related disasters pose risks that highlight a need for restructuring the dominant “sun, sea, and sand” and mass tourism, with excessive resort buildup on the coasts. These crises and disasters constantly disrupt island tourism, exacerbating the already volatile nature of the tourism industry, especially in the Caribbean. Therefore, the SEM which grounds an understanding of how the island system functions, coupled with the MLP that explains sustainability transitions, are proffered as an alternative and systematic approach to restructuring island tourism. In this regard, the models are analyzed for their application to the tourism accommodation subsector. The chapter concludes with the relevance of the models to policy makers and demonstrates how their application can minimize the risks posed by disasters and pandemics to materials and energy flows in the accommodation sector and eventually lead to sustainable island tourism.