Remote monitoring and control systems are being used with more frequency, but the characteristics of situational awareness and decision-making from remote locations are largely unknown. Remote operators’ sources of information differ from on-board sources greatly in terms of perspective, field of view, and available data type (qualitative or quantitative). This study focused on clarifying the cognitive effects of first- and third-person perspectives on ship handling. A working hypothesis was formulated based on the findings of visual information processing and previous studies and tested using a developed ship handling simulator. The results revealed that: (1) the cognitive characteristics of the first-person perspective make it more effective in safely guiding ship handling than does the third-person perspective, and (2) the deviation in cognitive characteristics is prominent where collision can be easily avoided. The findings will aid the development of on-board and remotely piloted vessels and ensure the safety of their crews.