Sail training is described as an educational endeavour where participants are required to adapt to an unfamiliar physical and social environment, acquire new skills (maritime and domestic), and confront personal challenges (e.g. going aloft, dealing with seasickness). It shares many of the philosophical underpinnings of adventure education, where personal and social growth is believed to be achieved through challenge and working as a team. Sail training has a focus on educational experiences "through" the sea rather than "for" the sea--thus practitioners need a combination of maritime and people management skills. This study looks at the motivation of crew to engage in sail training, the challenges they face, and what they believe would assist them to perform their role. This study contributes to the growing research on the professional development needs of 'incidental' outdoor educators and makes recommendations to address some of the challenges they face.