Described by Kerouac as being about "man's simple revolt from society as it is, with the inequalities, frustration, and self-inflicted agonies", the 158-page handwritten manuscript was Kerouac's first novel, but was not published during his lifetime. He wrote in his notes for the project that the characters were "the vanishing American, the big free by, the American Indian, the last of the pioneers, the last of the hoboes". The novel follows the fortunes of Wesley Martin, a man who Kerouac said "loved the sea with a strange, lonely love; the sea is his brother and sentences. He goes down."

Jack began this work not long after his first tour as a Merchant Marine on the S.S. Dorchester in the late summer of 1942 during which he kept a journal detailing the gritty daily routine of life at sea. Inspired by the trip, which exemplified Jack's love for adventure and the character traits of his fellow shipmates, the journals were spontaneous sketches of those experiences that were woven into a short novel soon after disembarking from the S.S. Dorchester in October of 1942.