The assesment of the safety of ship's transit in a curved narrow channl consists of the maneuvering safety determined by the chance of running aground, the maneuvering difficulty determined by shop's workload, and shiphandler's subjective evaluation. In this study to examine the correlation between shiphandler's subjectice evaluation and the maneuvering risk, the real-time and full-mission shiphandling simulator in the Korean Marine Training & Research Institutes(KMTRI) was utilized. In the conning bridge of the shiphandling simulator, 50 experienced masters conducted masters conducted the modeled vessel of 60,000 deadweight tonnage along the designed channel under 3 different envrinmental conditions. The findings were as follows: (1) The frequencies of stress levels, work difficulties, vessel controllability and overall workload of shiphandlers are similar irrespective of environmental conditions and they are able to be represented as shiphandler's subjective evaluation. (2) It is possible to assess and analyze theoretically the correlation between the shiphandler's subjective ecaluation and maneuvering risk each environmental cindition by quantifying the data obtioned from the tests. The results are as follows: ① As the degree of maneuvering risk increases, the shiphandler's subjective evaluation increases sharply near the curvature area of the desgined channel. ② In the area of the curvature of the designed channel, maneuvering risk increases sharply with the danger of running aground under the environmental condition of current and wind comung from the stem.