The assesment of the safety of ship's transit in a curved narrow channel consists of the maneuvering safety determined by the chance of running aground, the maneuvering difficulty determined by ship's workload, and shiphandler's subjective evaluation. In this study to examine the correlation between shiphandler's subjective evaluation and the maneuvering risk, the real-time and full-mission shiphandling simulator in the Korea Marine Training & Research Institutes(KMTRI) was utilized. On the conning bridge of the shiphandling simulator, 50 experienced masters conducted the modeled vessel of 60,000 deadweight tonnage along the designed channel under 3 different environmental 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 s possible to assess and analyze theoretically the correlation between the shiphandler's subjective evaluation and maneuvering risk under each environmental condition by quantifying the data obtained from the test. 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 designed channel. ② In the area of the curvature of the designed channel, maneuvering risk sincreases sharply with the danger of running aground under the environmental condition of current and wind coming from the stern.