Wellingborough Redburn’s father dies, leaving his wife and children poorly provided for, although he had been a highly successful merchant and at one time a wealthy man. The young Redburn is in his middle teens, and he decides to take some of the burden off his mother by going to sea. Given an old gun and a hunting jacket by an older brother, Redburn leaves his home by the Hudson River and goes to New York to seek a berth on a ship.

A college friend of his older brother aids Redburn in finding a berth on a ship bound for Liverpool, England. Unfortunately, the friend had emphasized to the ship’s crew that Redburn comes from a good family and has wealthy relatives; consequently, Captain Riga, master of the Highlander, is able to hire the young lad for only three dollars a month. Having spent all his money and unable to get an advance on his wages, Redburn has to pawn his gun for a shirt and cap to wear aboard ship.

During his first few days out of port, Redburn believes he has made a dreadful mistake in going to sea. Redburn’s fellow sailors jeer at him as a greenhorn. He makes many silly mistakes, becomes violently seasick, and discovers that he does not even have a spoon with which to take his portion of the food from the pots and pans. His coat proves inappropriate for life at sea; it shrinks after getting wet. His fellow crewmen find the odd coat amusing and give Redburn the nickname Buttons in derisive reference to the coat’s many buttons. Most horrifying of all is the suicide of a sailor who dived over the side of the ship in a fit of delirium tremens.

As the thirty-day cruise to Liverpool from New York wears on, Redburn learns how to make himself useful and comfortable aboard the ship. When he goes aloft alone to release the topmost sails, he earns a little respect from his fellow seamen, although they never do, throughout the voyage, let him forget that he is still inexperienced and had signed on as a “boy.” Redburn finds the sea fascinating in many ways; he also finds it terrifying, as when the Highlander had passed a derelict schooner on which three corpses were still bound to the railing.

For Redburn, one of the liveliest incidents of the voyage is the discovery of a little stowaway on board the Highlander. The small boy had been on board the vessel some months before, when his father had been a sailor signed on for a trip from Liverpool to New York. The father had since died, and the boy stowed himself away in an effort to return to England. Everyone on the ship, including the usually irascible Captain Riga, takes a liking to the homesick stowaway and make much of him.

Redburn has little in common with his fellow crew members, most of whom are rough fellows many years older than he. Through them, however, he receives an education quite different from that which he had been given in school. At first he tries to talk about church and good books to them, but he soon discovers that such conversation only irritates them into more than their usual profanity and obscenity. Redburn thinks that they are not really very bad men but that they had never had the chance to be good men. Most of all, he dislikes them because they look upon anyone who cannot follow the seaman’s trade as a fool.

A long, low skyline in the distance is Redburn’s first glimpse of Ireland. He meets his first European when an Irish fisherman hails the Highlander and asks for a line. After hauling fifteen or so fathoms of the line into his boat, the Irishman cuts the line, laughs, and sails away.

When the Highlander arrives at Liverpool, Redburn decides that the English city is not a great deal different from New York. Sailors and ships are the same everywhere, with a few notable exceptions. His trips into the city, away from the waterfront, and excursions into the Lancashire countryside convince him that he, as a foreigner, is not welcome. People distrust him because of his ragged clothing, and he has no money to purchase a new outfit, even though Captain Riga had advanced him three dollars, one month’s pay, upon the ship’s arrival in port.

Redburn’s greatest disappointment comes when he tries to use for his excursions an old guidebook he had brought from his father’s library. The guidebook, almost half a century old, is no longer reliable, for streets and structures it mentions are no longer in existence. Redburn feels that the whole world must have changed since his father’s time; he sees in the unreliable guidebook a hint that as the years pass the habits and ideals of youth have to be charted anew. Each generation, he learns, has to make its own guidebook through the world.

While in Liverpool, Redburn meets Harry Bolton, a young Englishman of good family but a prodigal son. Bolton says that he had shipped on two voyages to the East Indies; now he wants to emigrate to America. With Redburn’s help, Bolton is enrolled as a “boy” on the Highlander for its return trip to New York. The two boys, traveling on Bolton’s money, make a quick excursion to London before the ship sails, but they are back in Liverpool within forty-eight hours. Redburn sees little of England beyond the port where he had arrived.

On the return trip to America, the ship carries a load of Irish emigrants. Redburn quickly feels sorry for them but, at the same time, superior to the miserable wretches crowded between the decks. The steerage passengers suffer a great deal during the voyage. Their quarters are cramped at best, and during heavy weather, they cannot remain on deck. For cooking they have a stove placed on one of the hatches, one stove for five hundred people. Worst of all, an epidemic of fever breaks out, killing many of the emigrants and one of the sailors.

Bolton has a miserable trip, and Redburn feels sorry for him, too. The English boy had lied in saying he had been at sea before. Bolton cannot bear to go aloft in the rigging, and he, in place of Redburn, becomes the butt of all the jokes and horseplay the crew devises.

After the ship reaches America, however, the voyage seems to both Redburn and Bolton to have been a good one. They discover that they really hate to leave the vessel that had been home to them for several weeks. Their nostalgia for the vessel, however, is soon dissipated by Captain Riga. The captain dismisses Redburn without pay because the lad had left his duties for one day while the ship was at Liverpool. The captain even tells Redburn that he owes the ship money for tools he had dropped into the sea. Bolton is given a dollar and a half for his work; the pittance makes him so angry that he throws it back on the captain’s desk. The two boys then leave the ship, glad to be back on land once more.