Experimental studies of air entrainment by breaking waves are essential for advancing the understanding of these flows and creating valid models. The present study used three-dimensional simulations of a bow wave to examine its air entrainment process. The simulated waves were created by a deflecting plate mounted at an angle in a super-critical free surface flow. Since the air entrainment process is closely coupled with breaking wave dynamics, the present study included both air entrainment and free surface measurements. Measurements of the free surface wave were obtained from the simulated bow waves at two scales, and also from the bow wave created a towed wedge model. Contact line and bow wave profile measurements for the different experiments were compared, demonstrating the similarity of the experimental simulations to the towed model experiments. The plunging wave jet shape was measured in the larger scale stationary model and towed model experiments and used to calculate the jet thickness, velocity, and impingement angle. The bow wave profile data from the towed model experiments were used to investigate the scaling on the plunging wave face, and their wavelength, frequency, and velocity were measured. The primary mechanisms for air entrainment were the impact of the plunging wave jet and individual droplets in the splash region on the free surface. The air entrainment process was observed in the larger scale stationary model experiments, and the air bubbles were entrained in spatially periodic bubble clouds. Due to the shallow depth in these experiments, measurements of only the larger bubbles in the initial stages of air entrainment were obtained. An impedance based void fraction meter, developed specifically for the purpose, was used to measure the void fractions and bubble size distributions beneath the wave. The bubble cloud size and void fraction increased with downstream distance. There were indications that the surface disturbances control the periodicity of the bubble clouds. Namely, the surface disturbances divide the plunging liquid jet sheet into a series of plunging wave jets, each entraining air into a separate bubble cloud beneath the free surface.