Life on board merchant marine ships is very tough, very male, and isolated from much of the rest of the world by language, culture, and usually a large expanse of sea. This article presents data that show that leadership in this environment is full of aesthetic appreciation that is often relational, arising in interaction with others’ appreciation, and also full of strongly felt emotion. Those who exercise leadership on merchant marine ships (captains, chief engineers, first officers) turn out to have strong views on the importance of understanding aesthetics and emotions in discharging their responsibilities. We illuminate these leaders’ aesthetics and emotions about the sea and ships by comparing and contrasting them with those of a professional seascape painter