It’s late at night and Jim is tired, but he doesn’t want to leave the deck since he’s fascinated by everything going on. Long John Silver begins to sing the sailor song ending, “Yo-ho-ho, and a bottle of rum!”, which recalls to Jim the tunes of Billy Bones. But Jim is soon distracted by the preparations for departure: the anchor is pulled up and they sail off.
This is another clue that Long John Silver is more closely tied to the pirates Jim met than he thought, or at least tried to convince himself. Nonetheless, these points of similarity are not strong enough to cause Jim to worry.
Mr. Arrow soon turns out to be a disappointment: he lacks authority and command, and begins to spend most of the day drunk, though no one can figure out where he gets the liquor. One night he disappears overboard, neither shocking nor saddening the others.
To be a respectable authority figure on a ship, it seems, one must be careful not to lose the respect of the other people on board—a lesson that it appears Mr. Arrow was unable to follow.
The coxswain Israel Hands begins to take on some of the mate’s duties in place of Mr. Arrow. Hands is a confidant of Silver, and shares with Jim that Silver once used to be able to fight four men singlehandedly, before he lost his leg.
Jim begins to learn more about Silver’s past and his remarkable courage: his lost leg is a sign not of weakness but rather of his eagerness to fight.
Silver himself treats Jim kindly, often welcoming him into the galley with his parrot, whom he’s named Captain Flint after the pirate, and who repeats “Pieces of eight!” (a kind of silver coin) over and over. He tells Jim that the parrot has been to Madagascar, Surinam, and Providence: he’s too fond of her even to stop her from imitating the swear words she’s picked up.
This is yet another instance of Silver’s close ties to the world of pirates, piracy, and the hunt for treasure. The parrot Captain Flint will become a kind of motif that prepares the way for or signals the presence of Silver, who exerts as much power over the parrot as over other people.
Meanwhile, Captain Smollett and Squire Trelawney fail to hide their mutual dislike. Still, the Hispaniola sails well, and most of the crew seems content, especially because they’re often given “double grog” (a rum drink), “duff” (a pudding), and there’s a barrel of apples for anyone who’d like one. The captain disapproves of spoiling the crew this way, but Jim notes that it was this apple barrel that ended up saving all their lives.
Although the squire had hired the captain, the latter is too uptight for the squire’s liking, unwilling to “spoil” the cabin crew and, the squire thinks, overly fearful. Here, though, with a bit of foreshadowing, the narrator-Jim suggests that this lack of trust was ultimately misplaced.
Jim explains that on the last night before reaching land, he decides to grab an apple. He heads to the deck, climbs into the barrel, and is about to climb back out when he hears a few significant words spoken in Silver’s voice, so he remains silent and listens.
Jim has a good deal of freedom on the ship, and his ability to roam around is matched by his quick thinking when it seems that he might have something to learn or gain by spying.