An experimental study on drilling of stainless steel is conducted using TiAlN coated drills and HSS twist drills with several cutting conditions; feed rate, spindle rotational speed, and dry/wet cutting. The effects of number of hole on the thrust force are examined by cutting force measurement. The flank wear of the drills and the change of hole diameter are quantitatively observed using a vision system. It is found that the thrust force in drilling with TiAlN coated drills decrease under dry and wet machining, whereas the flank wear resistance is improved.