While enrolled at the Sailing Cadet school, Masefield attended a class instructed by "Wally" Blair, who, with his skill at spinning tales and relating stories of the sea, kindled and encouraged further Masefield’s desire for story telling. In fact, many of Blair’s stories were included in ‘Mainsail Haul’, a collection of prose written by Masefield and published in 1905.

In 1894, at the age of 16, Masefield boarded the Gilcruix, as an apprentice. The four masted ship’s destination was Chile, which entailed a voyage around Cape Horn. Interestingly, one of Masefield’s duties aboard the Gilcruix was to make daily entries into the ship’s journal.

Masefield’s first voyage brought to him the experience of sea sickness and a taste of the renowned fierce weather sailors generally encounter ‘rounding the Horn.’ He recorded his experiences of sickness and the conditions aboard the ship while sailing through the extreme weather ( he later vividly described the fury of a storm while rounding Cape Horn in a later poem, ‘Dauber’), however it was obvious from his journal entries that he delighted in viewing flying fish, porpoises, and birds unknown to him, and was awed by the beauty of nature, including a rare sighting of a nocturnal rainbow on his voyage.