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.