The Lagrangian separation distance between the endpoints of simulated and observed drifter trajectories is often used to assess the performance of numerical particle trajectory models. However, the separation distance fails to indicate relative model performance in weak and strong current regions, such as a continental shelf and its adjacent deep ocean. A new skill score is proposed based on the cumulative Lagrangian separation distances normalized by the associated cumulative trajectory lengths. This skill score is used to evaluate surface trajectories implied by Global HYCOM hindcast surface currents as gauged against actual satellite-tracked drifter trajectories in the eastern Gulf of Mexico during the 2010 Deepwater Horizon oil spill. It is found that the new skill score correctly indicates the relative performance of the Global HYCOM in modeling the strong currents of the Gulf of Mexico Loop Current and the Gulf Stream and the weaker currents of the West Florida Shelf. In contrast, the Lagrangian separation distance alone gives a misleading result. The proposed dimensionless skill score is particularly useful when the number of drifter trajectories is limited and neither a conventional Eulerian-based velocity nor a Lagrangian-based probability density function may be estimated.