The Republic of Trinidad and Tobago is an archipelagic Small Island Developing State (SIDS), situated on the southern end of the chain of Caribbean islands. Several factors such as climate, topography, and hydrological characteristics increase its susceptibility and vulnerability to flooding which results in adverse socio-economic impacts. Many Caribbean islands, including Trinidad and Tobago lack a flood risk assessment tool which is essential for a proactive mitigation approach to floods, specifically in the Caribbean due to the incommensurate flooding events that occur because of the inherent characteristics of SIDS. This research focuses on the problem of flooding using susceptibility analysis, vulnerability analysis and risk assessment for the island of Trinidad, whilst also presenting a repeatable and appropriate methodology to assess these risks in regions that have similar characteristics to Trinidad. This is especially useful in Caribbean countries because of a lack of internal human capacity to support such efforts. Flood hazard indexes (FHI) and vulnerability indexes (VI) were generated for this study using subjective and objective weighting technique models to identify regions that are affected by flooding. These models were Analytical Hierarchy Process (AHP), Frequency Ratio (FR) and Shannon’s Entropy (SE). Comparative analyses of the three models were conducted to assess the efficacy and accuracy of each to determine which is most suitable. These were used to conduct a risk assessment to identify risks associated with each Regional Corporation of Trinidad. Results indicate that FR is the most accurate weighting technique model to assess flood susceptibility and risk assessment in Trinidad, with an Area Under the Curve (AUC) of 0.76 and 0.64 respectively. This study provides an understanding of the most appropriate weighting techniques that can be used in regions where there are challenges in accessing comprehensive data sets and limitations as it relates to access to advanced technology and technical expertise. The results also provide reasonably accurate outcomes that can assist in identifying priority areas where further quantitative assessments may be required and where mitigation and management efforts should be focused. This is critical for SIDS where vulnerability to flooding is high while access to financial and human resources is limited.