Near-surface winds around the mountainous Caribbean islands contribute to orographic lifting and thermal diurnal rainfall that requires mesoscale analysis. Here, a new perspective is presented via high-resolution satellite and reanalysis products. Singular value decomposition is applied to 5 km cold-cloud duration satellite data to understand the leading mode of seasonal hydro-climate variability and its regional controls. The spatial loadings reflect wet islands in a dry marine climate, while temporal amplitude is modulated by the large-scale zonal circulation. When summer-time trade winds weaken, daytime confluence around Caribbean islands enlarges, gathering and lifting more moisture. In addition to the static geographic forcing, transient easterly waves impart the majority of marine rainfall between June and September. Higher resolution products capture the thermal orographic effect and reveal upward trends in island rainfall and soil moisture over the satellite era, while lower resolution products miss this effect. The climate of mountainous Caribbean islands is trending toward increased runoff and soil moisture.