Numerous structural, tectonic, and geometric aspects of the Eastern South Caribbean Plate Boundary Zone are assessed or reassessed in the light of seismic reflection data, field studies from 2000-2007, heavy mineral analysis, updated interpretation of seismic tomography, seismicity, GPS data, and refined plate kinematic constraints for the Cenozoic. We show that the Cretaceous passive margin of northern South America was transformed to a north-facing, slowly convergent margin in the Late Maastrichtian, and that the collision between the Caribbean and South America was a collision of two convergent margins above an intervening, "doubly subducting" Proto-Caribbean oceanic lithosphere. The new assessments are iteratively integrated to create semi-quantitative palinspastic reconstructions for 5, 10, 25, 31 and 42 Ma, on which paleogeographies are developed. The origin of key sandstone units are considered, due to their importance as major reservoirs, as well as the implications of the kinematic and dynamic modeling for structural timing. The primary collision between the two plates was completed by 10 Ma, with subsequent motion being essentially E-W strike slip, the deformations of which are driven mainly in a bow-wave model of transcurrent simple shear.