Feeling forsaken and friendless and like a "boy el [whom] nobody loved," Tom decides to turn to a life of crime. He meets Joe Harper, "his soul's sworn comrade," and they begin to lay their plans and decide to include Huck Finn as a member of their gang of pirates. Huck, having no qualms about which life of crime is the best, readily agrees, and the three plan to meet that night.
When they meet at the appointed place, each boy identifies himself by his assumed pirate name; then they "borrow" (or capture) a small log raft to take them to Jackson's Island where they make camp. The following afternoon, the boys hear an unusual sound--a "deep, sullen boom came floating down out of the distance"--and see a ferry crowded with townspeople. Tom realizes that "somebody's drowned." After spending a few moments wondering who, the boys realize that the townspeople think they have drowned. All three are excited and overjoyed at the thought that they are the center of attention and will be the envy of all of their companions. When Joe vaguely hints that maybe they should go home because of the grief their families must be feeling, Huck and Tom ridicule him. When Huck and Joe go to sleep, however, Tom writes two notes; he leaves one note in Joe's hat; he keeps the other note and wends his way to the sandbar.
The reasons for the escape to Jackson's Island are varied. Tom feels depressed and dejected because of Becky Thatcher's rejection of him. Joe Harper's situation is similar: He is depressed because his mother punished him for throwing out some cream--a crime of which he is innocent. (Later, in fact, his mother will despair after Joe is "dead" because she remembers throwing out the cream herself.) Like Tom, Joe wants to escape "civilization," but he is also the first to tire of the island and the first who wants to return to his family. For Huck Finn, who has no responsibilities and no one to notice that he is gone, one place is as good as another.
Each boy assumes a pirate name, and these names come from books that Tom has read. Twain makes a subtle, albeit important contrast from the natural common sense intelligence of Huck Finn to the acquired fanciful ideas that Tom Sawyer gets from his books. Tom, for example, has idealized ideas about what pirates look like and how they act--based on the various books that he has read. Tom shares his knowledge of pirates (gained from his book reading) with the other boys. He explains how pirates capture and burn ships, take and bury treasure, and kill the men and carry the women away to their island. When Tom points out that pirates also wear gaudy clothing and gold, silver, and precious jewels, Huck looks at his rags and faces the reality that he "ain't dressed fit for a pirate."
The first day on the island is one of the most glorious days in the boys' lives, one lived to the fullest. But at night, Tom and Joe, who have basically the same upbringing, have guilty consciences over stealing food for the outing. Even though they say their bedtime prayers (something Huck would never bother with), their consciences do not let them sleep. Their conscience is an ironic contrast to their boastful talk of capturing ships, stealing, killing men, and kidnapping women. In contrast, Huck Finn has no pangs of conscience. He feels no qualms about having lifted (stolen) certain items; he feels no compunction to live by the rules of a society that has made him an outcast. He has had a marvelous day because he is getting more to eat than he usually gets in the village. For Huck, this life on the island is an idyllic existence, especially since neither he nor Tom have any thoughts of the grim aspects of the grave robbery and the murder of Dr. Robinson. On this island, there is no feeling of terror and no talk of superstitions.
When Tom awakes the next morning, he feels himself at one with nature; he thrills merely watching the antics of birds and even insects. When Huck and Joe awake, their day is filled with natural joys and contentment; a sense of quiet joy pervades their lives--"here was a delicious sense of repose and peace in the deep pervading calm and silence of the woods." The realization that their raft has floated away makes them realize that they have truly escaped from society and are isolated and abandoned. Twain has thus presented the perfect life. However, soon the sounds of thunder turn into cannon fire and the mood drastically changes. A ferryboat descends upon them, bringing the society from which the boys have escaped. When the boys realize that the ferryboat is searching for them--everyone believes they have drowned--they initially like the idea of being cried over and of causing suffering to those who have been mean to them. It is not long, however, before Tom and Joe are concerned because they know how their families must be are grieving. Huck, who has no family, does not share this concern.
Chapter 14 ends with Joe wanting to return home only to be talked out of it by Tom. Tom himself waits for his friends to sleep and he quietly slips away, and the chapter ends with this mystery.