<p>The present study examines the critical sociological and economic characteristics and the aspirations of students belonging to Generation Z, commonly called Gen Zers, who aim to become seafarers by enrolling in the Merchant Marine Academies (MMAs) of a traditional maritime nation, Greece. Benefiting from generational studies and the literature on marine education and training (MET), our study empirically explores the sociological background, motivations, and approach to seafaring among Generation Z students who choose to pursue a career at sea. The research is based on an analysis of a database containing 2,833 survey responses from first-year Gen Z students enrolled in Greek MMAs collected during the first months of the three latest academic years (2020–2023). The findings reveal that Gen Zers make calculated career decisions, placing greater importance on factors such as professional stability and security and career development opportunities, with family tradition playing a less significant role than in the past. Given their reliance on the digital world, Gen Zers consider internet access to be a critical factor in selecting an employer. The large number of female students is also a defining characteristic of Gen Zers, creating prospects for increasing the participation of women in the traditionally male-dominated profession of merchant marine officers.</p>