This paper examines historical and future changes in normalised damages resulting from climate-related natural disasters for the Caribbean. Annualised damages of USD824 million are shown to be non-stationary over the historical period 1964 to 2013. Perturbations of (i) sea surface temperatures (SST) in the tropical North Atlantic (TNA) and (ii) the Atlantic multi-decadal oscillation (AMO) appear to be associated with historical damages. Both the TNA and AMO are known modulators of hurricane activity and rainfall amounts in the Caribbean. Indicative future damages are determined using (i) cumulative distribution functions (CDFs) of perturbed climate states and (ii) an artificial neural network (ANN) model of damages using projected TNA values and the state of the AMO derived from an ensemble of five coupled model intercomparison project phase 5 (CMIP5) global climate models (GCMs) run under the RCP 4.5 scenario. Estimates of future damages are determined when global mean surface temperatures (GMST) reach and exceed 1.5 °C above preindustrial levels. Annual normalised damages may potentially increase to at least USD1395 million or close to double for 1.5 °C. At 2 °C, higher damages may occur; however, large uncertainty across all GCMs prohibits the identification of significant difference between 1.5 and 2 °C. Significant differences in damages do, however, exist for at least two of the GCMs for the two climate states. The robustness of the results is discussed in light of a number of issues, including limitations associated with the data.