The maneuvering skills such as situation awareness and maneuvering strategies are essential for safe navigation. However, there is no clearly established training method for improving them in the education of inexperienced navigators, and their improvement is dependent on the experience of maneuvering on the company’s vessels, which is why we need to develop a new educational program which ensures passing down them to inexperienced navigators. The purpose of this study is to develop the program of objective structured navigational education and training for inexperienced navigators. It helps them objectively to learn and train the maneuvering skills of professional navigators via quantitative data and to evaluate their acquisition status in simulator education. In this research, we develop useful training scenarios for constructing the program. We create six training scenarios via questionnaire survey for twenty professional navigators regarding avoiding maneuvers and evaluate their usefulness via survey with questionnaire and interview in the simulator experiment using four of the six training scenarios. The results of the experiment survey indicate that each scenario is appropriate difficulty of level for educational purpose, has various educational contents about maneuvering skills, and hardly needs to be improved. That is why we develop useful training scenarios for the new educational program.