This paper seeks to examine the attitudes of millennial maritime students when it comes to career planning and proactive behavior, in order to efficiently, effectively develop each students’ potential, and direct the activities of decision-makers (maritime companies and educational institutions). This research was based on a purposefully developed conceptual model and empirical research conducted on a sample of 308 students from Montenegro and Turkey. The research relied on a referential career engagement scale. The relevance of the hypotheses was tested by means of SEM model, logistic regression, Kruskal-Wallis test and eta coefficient. The results obtained show that proactive behavior of maritime students is a consequence of their attitudes established concerning career development. However, the attitudes of students vary depending on their country of origin and the year of their studies. Thus, through the influence on attitudes these two factors indirectly affect the proactive behavior of students. This emphasizes the posibility to foster students’ proactive behavior regarding maritime career planing through effectively management of public policies of the country, especially those related to the educational system. These findings explain the relationships between the students and their career planning and proactive behavior, strengthening the students’ competitivity on the market. Therefore, the paper provides a significant contribution in offering insights to decision-makers and the creators of educational policies.