It can be said that the relationship between the maneuvering ability of operators and the navigational environment affects the safe degree of navigation in the collision avoidance situation. In order to reduce the occurrence probability of accident and to maintain the safety, it is necessary to clarify the relationship between human behavior and navigational environment. In this study, therefore, we analyzed and discussed the relationship between the maneuvering characteristics and the safety focused on human behavior as a fundamental factor of marine accidents using ship handling simulator and questionnaire. As a result, we concluded that navigational environment changes variously and the maneuvering ability of operators also varies with the navigational environment, and the ship handling characteristics strongly affect the occurrence probability of accident.