The history of a yacht began with a sail attached to a vessel, and such yachting is the game competing for a speed by operating a yacht only though wind force, and a sports in which yachters challenge the limitations of human abilities against rough nature, and vie for human mentality and physical strength. However, due to the awareness that yachting is a luxury sports yet, it fails to get established as general public’s sport for all. Thanks to the recent increase in income and expansion of leisure time, the public concern for yachting is ever increasing through yearning for marine sports as a new sport, and as a means of diversification strategy for Olympic medals led by the government; further, with the increase in commercial value, such as mariner business related to a yacht, the concern for yachting is getting higher not only among the government, companies and yachters but also among the general public. Accordingly, it’s necessary to provide the opportunity for people to enjoy marine sports and expand the base of yachting population through revitalization of yachting and promotion of yacht industry at such a level. However, it’s difficult for the public to contact sailing yacht due to log-distance movement, expensive equipment and lots of required time, etc. Moreover, it’s necessary to obtain the Boat Operator’ License in order to run a sailing yacht according to the Water-related Leisure Activities Safety Act. Accordingly, this study is intending to propose the education & training needed for Boat Operator’s License test consequent on a scenario through a simulator that makes it possible to do basic operation of sailing yacht, and to do operation skills improvement training, and Smart sailing yacht operation license test evaluation system available in time of sailing yacht operation license test in a virtual simulation and on the actual sea.