This paper investigates the maneuvering characteristics of a planing hull free to move in heave and pitch directions undergoing a steady drift test. Results assess and compare predictions from Computational Fluid Dynamics (CFD) Detached Eddy Simulation (DES) and a 2D + t strip theory models against available experimental data from Katayama et al. (2005). At high yaw angles and high Froude numbers of predictions from both models marginally deviate from the experimental longitudinal force measurements. Whereas strip theory confronts difficulties in predicting dynamic trim angle and CG rise-up when either Froude number or yaw angle increases and hence nonlinear hydrodynamics prevail, CFD generally agrees well with experimental data. The CFD model is seen to result in numerical ventilation in zero-drift cases, leading to lower pressure and a localized reduction in the skin friction coefficient. These phenomena are hypothesized to contribute to the under-prediction of trim angle and longitudinal force in zero-drift scenarios. Strip theory provides less reliable results in terms of predicting the sway forces at larger yaw angles, the yaw moment at low Froude numbers and sway forces and associated maximum pressures near the stagnation line. This model cannot capture the asymmetric pressure distribution that emerges on the bottom of the hull at large speed and yaw angles, which is likely to be one of the reasons for errors in predicting the side force. Detached Eddy Simulations demonstrate the strong asymmetric vorticity field formation on the exposed side of the hull at nonzero drift angle. This means that added masses used in the 2D + t model can cause large errors in equilibrium predictions.