Hurricane Maria had a large impact on the U.S. Caribbean, causing massive vegetation loss and landslides with its passing on September 20, 2017. We studied the causes of the spatial variation of the vegetation loss and landslide occurrence using satellite and aerial imagery and modeling. Landscape-wide models were made that fit the observed vegetation ‘greenness’ loss (related to canopy structure as seen by satellites) and the landslide occurrence, using hurricane forces of wind and rain, as well as landscape characteristics. The model of greenness loss showed the U.S. Caribbean lost 31% of its initial greenness from the hurricane, with 51% lost from the initial in the Luquillo Experimental Forest from Hurricane Maria along with the 2-week earlier (smaller) effect of Hurricane Irma. More greenness disturbance was seen in areas with less wind sheltering, higher elevation and topographic sides. The model of landslide occurrence showed the U.S. Caribbean had 34% of its area and 52% of the Luquillo Experimental Forest area with a landslide density of at least one in 1 km2 from Hurricane Maria. Four experiments with parameters from previous storms of wind speed, storm duration, rainfall, and forest structure over the same storm path and topographic landscape were run as examples of possible future scenarios. While intensity of the storm makes by far the largest scenario difference, forest fragmentation makes a sizable difference especially in vulnerable areas of high clay content or high wind susceptibility. Resource managers should carefully manage these areas in the future. Such models could be useful in quickly predicting the effects of approaching hurricanes, especially with large hurricanes that are likely to push landscapes past their abilities to absorb the forces without disturbance.