The purpose of this study is to analyse data from the marine pilots’ bio-sensor readings to determine how experience affects their biometrical response during the port approach. The experiences play a significant role in the participant’s decision-making process and correlate with the repetitions. Through the repetitions of the experimental task, the participants gain experience, which correlates with the biometrical response, e.g., heart rate, electrodermal activity, etc. After exposing the two experience-distinct groups of participants to the same simulated port-approaching task, their collected biometric data is analysed and discussed. The results show that biometrical readings of the less experienced participants typically vary compared to that of the experienced participants, who take the simulated task more seriously. The study also yields insight into the workload process, involving disturbing factors during the task.