We analyze western Caribbean structural styles and depositional controls associated with Late Cretaceous–Cenozoic deformational events using a 1600-km (994-mi)-long, regional, northwest–southeast transect extending from the Cayman Trough in Honduras to northern Colombia. Different structural provinces defined along the transect include (1) the Cayman Trough and adjacent Honduran borderlands marking the North American–Caribbean transtensional plate boundary characterized by late Eocene–Holocene fault-controlled depocenters; (2) the Nicaraguan Rise that includes continental Paleocene–Eocene rocks deposited in sag basins, which are overlain by relatively undeformed Miocene–Holocene carbonate and clastic shelf deposits of the northern Nicaraguan Rise, following a Late Cretaceous convergent phase; (3) the Colombian Basin that includes thick Miocene clastic depocenters and the localized presence of Upper Cretaceous rocks overlying the basement and where much of the subsidence is likely isostatic and flexurally driven given its proximity to the subduction zone of northern Colombia; (4) the south Caribbean deformed belt, an active, accretionary prism produced by the subduction of the Caribbean large igneous province beneath the South American plate, which has deformed the Cenozoic prism and fore-arc section and produced thrust-fault–controlled accommodation space for upper Miocene–Holocene piggyback deposits; and (5) the onshore Cesar–Rancheria Basin in northern Colombia, which has recorded the uplift of its bounding mountain ranges, the Sierra de Santa Marta massif to the west and Perija Range to the east. Plate reconstructions place the various crustal provinces along the transect into the context of the Late Cretaceous–Cenozoic deformation events that can be partitioned into strike-slip, convergent, and extensional components.