The Netherlands Leeward Antilles volcanic island arc is an ideal natural laboratory to study the evolution of the Caribbean-South American plate boundary. The Leeward Antilles islands (Aruba, Curacao, and Bonaire) are located offshore western Venezuela, within the obliquely convergent diffuse plate boundary zone. Outcrop analysis, microthermometry, and 2D marine seismic reflection data provide evidence of three generations of regional deformation since the Late Cretaceous. Outcrop analysis of structural features, including faults, joints, and veins, characterizes the kinematic history of the islands. Fluid inclusion analysis of quartz and calcite veins coupled with apatite fission-track dating provides the island exhumation history. Finally, marine reflection seismic data processing and interpretation of newly acquired data elucidates offshore structures to integrate with our onshore results. The oldest regional deformation, resulting in both ductile (D1) and brittle (F 1) structures, is attributed to displacement partitioning along the arcuate Caribbean plate boundary. Associated crustal thinning initiated island exhumation, at a rate of 0.18 km/my, from a maximum burial depth of 6 km in the Late Cretaceous (∼89 Ma). Coeval with D1/F1 deformation and exhumation, stretching of the island arc resulted in extensive basin rifting that separated the island blocks. At ∼55 Ma, a change in the relative motion of the Caribbean plate altered plate boundary dynamics. Displacement along the right-lateral Caribbean transform fault and Oca - San Sebastian - El Pilar strike-slip fault system created a wrench tectonic regime within the diffuse plate boundary zone. A second generation of brittle structures (F2) developed while the islands were at a maximum burial depth of 2 km during the Paleocene/Eocene. Since ∼45 Ma, continued motion along the strike-slip fault systems and oblique plate convergence resulted in the youngest generation of structural features (F3). Regional tectonics control the ongoing steady-state exhumation of the islands at a rate of 0.04 km/my. Most recently, the northeast escape of the Maracaibo block also drives deformation within the diffuse plate boundary zone. Overall, the Caribbean-South American plate boundary geometry has evolved with diachronous deformation, from west to east, accompanied by 135° of clockwise block rotation during collision and accretion of the Leeward Antilles since the Late Cretaceous.