Upon reaching Chile, Masefield suffered from sunstroke and was hospitalized. He eventually returned home to England as a passenger aboard a steam ship, rather than as a crew member.

In 1895, Masefield reluctantly returned to sea, at the urging of his Aunt, on another windjammer destined for New York City. However, the urge to become a writer and the hopelessness of life as a sailor in achieving that goal overtook him, and in New York, Masefield deserted his ship. As a 17 year old in a strange country, unable to secure employment, he traveled through the country side, taking whatever job he could find including farm labour. Often, he was forced to sleep outdoors, under the stars, without much to eat.