In this study, a partially submerged vertical cylinder is moved at constant velocity through water, which is initially at rest. During the motion, the wake behind the cylinder induces freesurface deformation. Eleven cylinders, with diameters from D = 1.4 to 16 cm, were tested at two different conditions: (i) constant immersed height h and (ii) constant h/D. The range of translation velocities and diameters are in the regime of turbulent wake with experiments carried out for 4500 < Re < 240 000 and 0.2 < F r < 2.4, where Re and F r are the Reynolds and Froude numbers based on D. The focus here is on drag force measurements and relatively strong freesurface deformation up to air-entrainment. Specifically, two modes of air-entraiment have been uncovered: (i) in the cavity along the cylinder wall and (ii) in the wake of the cylinder. A scaling for the critical velocity for air-entrainment in the cavity has been observed in agreement with a simple model. Furthermore, for F r > 1.2, the drag force varies linearly with F r. c for h = 23 ± 0.1 cm and F r −4.7±0.51 c for h/D = 2.55 ± 0.05, in good agreement with the prediction of the model. The red shaded area refers to the range of dimensionless parameters where no air-entrainment in the cavity occurs. The black dashed-doted line represents the threshold Re/F r 25 000 above which air-entrainment occurs in the wake and in the cavity.Hence, air-entrainment requires large inertial effects or strong gravity effects. It is interesting to note that the stability diagram in Fig. 9(b) is consistent with the results of Kumagai et al.[42] for horizontal cylinder translating beneath an air-water interface.