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 the professional data regarding to situation awareness and maneuvering strategies. We evaluate situation awareness via mental workload calculated from heart rate variability and evaluate maneuvering strategies via voyage data and videos. We respectively set some assessment points and aggregate the data for them. The results show us the levels of alert intensity for each ship handling event, maneuvering methods, or criteria in maneuvering. That is why we develop professional data which shows situation awareness and maneuvering strategies of professional navigators in numerical values and trends.