Subsurface float and surface drifter observations illustrate the structure, evolution, and eventual demise of 10 North Brazil Current (NBC) rings as they approached and collided with the Lesser Antilles in the western tropical Atlantic Ocean. Upon encountering the shoaling topography east of the Lesser Antilles, most of the rings were deflected abruptly northward and several were observed to completely engulf the island of Barbados. The near-surface and subthermocline layers of two rings were observed to cleave or separate upon encountering shoaling bathymetry between Tobago and Barbados, with the resulting portions each retaining an independent and coherent ringlike vortical circulation. Surface drifters and shallow (250 m) subsurface floats that looped within NBC rings were more likely to enter the Caribbean through the passages of the Lesser Antilles than were deeper (500 or 900 m) floats, indicating that the regional bathymetry preferentially inhibits transport of intermediate-depth ring components. No evidence was found for the wholesale passage of rings through the island chain.