The idealization of the figure of the “true sailor,” always a professional, has paralleled the development of pleasure sailing since the second half of the nineteenth century as leisure boating has had a hard time finding legitimacy among professional sailors. A selection of iconic professional seamen is studied here, including the fisherman, the naval officer and the ocean racer. This paper investigates the way in which the figures of these “real seamen” and the debatable issues of contemporary pleasure sailing relate.