Maritime transportation consists of various situations such as navigation in the ocean, ship handling at harbor entrances, cargo handling and mooring in harbors. Generally, ships are built for the purpose of currying people and materials upon the seas. In order to accomplish the mission, a ship must be built to withstand the rigors of heavy weather and waves. In particular, the safety of ship motions at the entering/departing harbor and mooring under the effects of waves is very important for ship operation from the viewpoint of marine engineering. Therefore, safety and efficiency during entrance, departure, and mooring are extremely important aspects in the evaluation of ship operations from viewpoints of ship motions. However, the ship motions near a harbor entrance are not observed or studied as much. In this paper, to evaluate the difficulty of ship operations, field observations were performed using a new observation system with high accuracy in typhoon seasons, and grasp was done concerning about the time series characteristic that ship motions change rapidly within a harbor. Namely, such observations enable the quantitative safety evaluation under the effects of waves during ships entering and departing harbors in heavy weather.