The Caribbean region is highly vulnerable to multiple hazards. Resultant impacts may be derived from single or multiple cascading risks caused by hydrological-meteorological, seismic, geologic, or anthropological triggers, disturbances, or events. Studies suggest that event records and data related to hazards, risk, damage, and loss are limited in this region. National Disaster Risk Reduction (DRR) planning and response require data of sufficient quantity and quality to generate actionable information, statistical inferences, and insights to guide continual policy improvements for effective DRR, national preparedness, and response in both time and space. To address this knowledge gap, we review the current state of knowledge, data, models, and tools, identifying potential opportunities, capacity needs, and long-term benefits for integrating Earth Observation (EO) understanding, data, models, and tools to further enhance and strengthen the national DRR framework using two common disasters in Jamaica: floods and landslides. This review serves as an analysis of the current state of DRR management and assess future opportunities. Equally, to illustrate and guide other United Nations Disaster Risk Reduction (UNDRR) priority countries in the Pacific region, known as Small Island Developing States (SIDS), to grapple with threats of multiple and compounding hazards in the face of increasing frequency, intensity, and duration of extreme weather events, and climate change impact.