The Caribbean–North America plate boundary in the northeastern Caribbean shows a remarkable example of along-strike transition from plate boundary–normal subduction in the Lesser Antilles, oblique subduction with no strain partitioning in Puerto Rico, and oblique subduction/collision with strain partitioning further west in Hispaniola. We show that this segmentation is well marked in the interseismic strain, as measured using space geodetic data, and in the Neogene deformation regime, as derived from geological observations. Hence, interseismic segmentation, which reproduces the geological segmentation persistent over a long time interval, is inherited from the geological history and long-term properties of the plate boundary. This result is relevant to the assessment of seismic hazard at convergent plate boundaries, where geodetic measurements often show interseismic segmentation between fully–and partially–coupled plate interface regions.