This study attempted to investigate the hydrodynamic performance of various pentamaran configurations with a focus on the interference flow around the component hulls. A computer simulation was conducted based on Michell’s thin ship theory alongside a commercial CFD computation as a comparison. Experiments in the towing tank were performed to validate the numerical calculations, resulting in some hydrodynamic characteristics on the far-field wave pattern, wave interference, wave resistance, and total resistance. Analyses on both transversal and divergent waves were performed to assess the magnitude of wave resistance occurring due to the placement of the side hull to the main hull. Analyses on both waves were also conducted to assess the magnitude of wave resistance due to the placement of outriggers. Looking at the results, numerical calculations based on Michell’s theory were in parallel with experimental data, particularly at Fn greater than .4. Michell’s theory was observed as doing a little preferable agreement with the results of experiments than CFD. Besides, flow patterns obtained numerically from Michell’s and CFD analyses appeared as identical to photographs observed in a towing tank. This investigation identified that a configuration with aligning placement of the main to side hull on the formation of arrow tri-hull, near the Kelvin angle, would cancel the wave formed by the leading hull and can be used as a practical setting to reduce the total wave resistance.