The mesoscale structure of the circulation and convection over central Caribbean Antilles islands in midsummer is analyzed. Afternoon thunderstorms are frequent over islands such as Hispaniola and Jamaica as confluent trade winds circulate over heated mountainous topography. Observational data from a rain gauge network, profiles from aircraft and radiosonde, satellite estimates of rainfall, and mesoscale reanalysis fields are studied with a focus on July 2007. A statistical decomposition of 3-hourly high-resolution satellite rainfall reveals an “island mode” with afternoon convection. Trade winds pass over the mountains of Hispaniola and Jamaica with a Froude number <1, leading to a long meandering wake. The Weather Research and Forecasting model is used to simulate climatic conditions during July 2007. The model correctly locates areas of diurnal rainfall that develop because of island heat fluxes, confluent sea breezes, and mountain wakes.