To maintain situation awareness (SA) when exposed to emergencies during pilotage, a pilot needs to selectively allocate attentional resources to perceive critical status information about ships and environments. Although it is important to continuously monitor a pilot’s SA, its relationship with attention is still not fully understood in ship pilotage. This study performs bridge simulation experiments that include vessel departure, navigation in the fairway, encounters, poor visibility, and anchoring scenes with 13 pilots (mean = 11.3 and standard deviation = 1.4 of experience). Individuals were divided into two SA group levels based on the Situation Awareness Rating Technology (SART-2) score (mean = 20.13 and standard deviation = 5.83) after the experiments. The visual patterns using different SA groups were examined using heat maps and scan paths based on pilots’ fixations and saccade data. The preliminary visual analyses of the heat maps and scan paths indicate that the pilots’ attentional distribution is modulated by the SA level. That is, the most concerning areas of interest (AOIs) for pilots in the high and low SA groups are outside the window (AOI-2) and electronic charts (AOI-1), respectively. Subsequently, permutation simulations were utilized to identify statistical differences between the pilots’ eye-tracking metrics and SA. The results of the statistical analyses show that the fixation and saccade metrics are affected by the SA level in different AOIs across the five scenes, which confirms the findings of previous studies. In encounter scenes, the pilots’ SA level is correlated with the fixation and saccade metrics: fixation count (
p
= 0.034 < 0.05 in AOI-1 and
p
= 0.032 < 0.05 in AOI-2), fixation duration (
p
= 0.043 < 0.05 in AOI-1 and
p
= 0.014 < 0.05 in AOI-2), and saccade count (
p
= 0.086 < 0.1 in AOI-1 and
p
= 0.054 < 0.1 in AOI-2). This was determined by the fixation count (
p
= 0.024 < 0.05 in AOI-1 and
p
= 0.034 < 0.05 in AOI-2), fixation duration (
p
= 0.036 < 0.05 in AOI-1 and
p
= 0.047 < 0.05 in AOI-2), and saccade duration (
p
= 0.05 ≤ 0.05 in AOI-1 and
p
= 0.042 < 0.05 in AOI-2) in poor-visibility scenes. In the remaining scenes, the SA could not be measured using eye movements alone. This study lays a foundation for the cognitive mechanism recognition of pilots based on SA via eye-tracking technology, which provides a reference to establish cognitive competency standards in preliminary pilot screenings.