Tropical cyclones are natural events that transform into natural disasters as they approach and reach land. In 2017 alone, tropical cyclones caused an estimated $215 billion in damage. While MODIS data are regularly used in the analysis of hurricanes and typhoons, damage studies typically focus on just a few events without providing a comprehensive overview and comparison across events. The MODIS record is now sufficiently long to enable standardization in time, allowing us to extend previously developed disturbance methodology and to remove dependency on land cover datasets. We apply this new approach to detect the impact of both droughts and hurricanes on the four largest Caribbean islands since 2001. We find that the percentage of disturbed land on the four islands varies from approximately 0–50% between 2001 and 2017, with the highest percentages coinciding with major droughts in Cuba, and Hurricane Maria in Puerto Rico. We demonstrate that (1) Hurricane Maria resulted in significant disturbance across 50% of Puerto Rico (4549 km2), and (2) gradual recovery started about 2.5 months after the hurricane hit. While our approach focuses on the identification of damage arising from hurricanes, it is also capable of identifying the damage from droughts. This approach ultimately enables a better understanding of the combined effects of these two natural hazards across island landscapes.