This research examines the professional careers of yachting athletes throughout their histories of life. Using as a theoretical basis the studies of narratives, stories and storytelling, the research explores how sailors attribute meaning and narrativize their professional journeys. The study aims to understand which stories emerge from the narratives about the career trajectories of high-performance sport sailing athletes. In terms of methodological procedures, the research is qualitative and the testimonies were collected through interviews. When conducting the interviews, we sought to understand the stories related to the construction of each career, from the first contact with the sport until the moment in which a professional career started, considering the transitions experienced throughout the process. For data analysis, thematic examination was carried out, based on the proposition of five themes addressed in the different narratives: (1) stories about the origin; (2) stories about career planning; (3) stories of opportunities; (4) stories of challenges and how those were met; and (5) success stories. The several pieces of data indicate that most athletes face difficulties maintaining their professional careers while having to make ends meet. Great importance is attributed to the family and social context as influence factors, regarding the introduction to the sport. The family environment is highlighted when it comes to guidance and planning in the professional trajectory of these young sailors. It was observed that organizations and entities linked to sports are constantly present on the development of their careers in yachting. This study reveals challenges and achievements faced in the trajectory of these sailors, and thus contribute to improvements in high performance career management in the sport.