This study examines the dynamics of late spring rainfall (the Early Rainy Season, ERS) in the Caribbean region, in hopes of identifying mechanistic-based predictors for low-frequency climate modulations of the system. The subtropical Caribbean rain-belt develops in May as seasonal warming proceeds. By July, the rain-belt retreats north apparently following the westerlies and their vigorous synoptic disturbances. Daily climatology data suggest a physical definition of the Caribbean ERS as mid-May to mid-late June. Based on an examination of daily loops for several seasons, we hypothesize that rainfall occurs quasi-randomly throughout tongues of air with sufficiently high (above 45–50 mm) precipitable water (PW). These moist airmasses are brought north from the deep tropics by low-level southerlies, and typically bent over into SW-NE bands by latitudinal shear of the westerlies. The low-level flow that transports PW tongues is partly induced by upper-level synoptic disturbances in the westerlies, but also involves the gentle persistent flow around a geographically anchored Panama Low. While forced ascent is sometimes active ahead of these upper-level troughs, convective and mesoscale processes can produce rain wherever PW is sufficient. In summary, we hypothesize that rainfall hinges largely on the Lagrangian statistics of moist air tongues. Comparison is drawn between the Caribbean rain-belt and its East Asian counterpart (Meiyu-Baiu), and other mechanisms and diagnostics from that literature are discussed. Statistical prediction exercises, based on mechanistically chosen predictors, could both test hypotheses and aid local agricultural interests in the region.