When a high-speed body with cavity passes through water-air free surface and exits water, its mechanical environment and dynamic characteristics change significantly due to the great difference in density and viscosity between water and air. With focusing on this problem, the Computational Fluid Dynamics (CFD) method is applied to perform numerical calculation on the process of this vapor-liquid-gas flow during the water exit of a high-speed cylinder, with the Volume of Fraction (VOF) multiphase flow interface-capturing techniques and the overset grid technology. After the verification and validation of the CFD model through mesh convergence study and a water-entry experiment, cavity evolution and flow characteristics including pressure and velocity distribution during the water exit are analyzed. The effects of different initial velocities on the pressure distribution and drag characteristics of the cylinder are investigated. Calculated results show that the cavity collapse during water exit causes strong pressure fluctuation on the cylinder; when the cylinder exits water enveloped in a supercavity, the pressure distribution on its wall surface and surrounding water region is relatively uniform, and the drag changes gently, and thus the cylinder has good motion stability.