This study deals with drilling kinematics by planetary mechanism, adopted tool performances and cutter wear phenomena. Recently lightweight materials such as CFRP or titanium alloy are widely used as structural materials in aviation and aerospace industries for the purpose of mass reduction. Although these materials have characteristics of lightweight and high strength, they are regarded as difficult-to-cut materials. Planetary mechanism drilling is one of effective drilling methods for difficult-to-cut materials. The advantages of planetary mechanism drilling are short machining time, high-quality drilled holes and long tool lifetime. In this study, three types of tools for the planetary mechanism drilling were developed on the basis of kinematics of the cutting edges. Through the experimental results of tool wear or cutting edge observation, cutter performance of the tools and tool lifetime were made clear.