Relatively little scholarship has compared the ecological impact of acute climate-related events versus chronic human pressures. Despite mounting pressures from climate change and rapid tourism development across the Caribbean, even less research has assessed the relative impacts of biophysical versus anthropogenic pressures on the region's island landscapes. We compare the effects of an extreme climate event in the years immediately following Hurricane Mitch in 1998 relative to thirty years of rapid urbanization and tourism development on Roatan, Honduras. Results from a random forest classifier applied to thirteen Landsat Thematic Mapper (TM) and Operational Land Imager (OLI) scenes, indicate that between 1985 and 2015 urban area increased by 982.8 ha (227.7%), with 224.1 ha (-19.1%) of mangroves converted to urban areas. This compares to a 37% (384.9 ha) decrease in mangroves immediately following Hurricane Mitch. Mangroves in protected areas have fully recovered since Mitch, demonstrating their resiliency. Despite being illegal, mangrove deforestation across all unprotected areas accelerated to accommodate increasing urban area. Given that mangroves provide vital protection to an island's coastline and represent a major carbon-sink, and that extreme hurricanes in the Caribbean are projected to double in the coming decades due to climate change, this research suggests that rapid urbanization and tourism development in the Caribbean may decrease island ecosystem resiliency to environmental stressors.