The narrator knows that the captain would take all measures against his flight if he knew of it, including having other shipmates turn him in, so the narrator remains silent even though he greatly anticipates his freedom. Walking the deck one night, the narrator sees Toby, a fellow shipmate, lost in a reverie while staring overboard. Toby is a young, adventurous man, who is quiet, rarely smiles, and never speaks of his past. The narrator decides that it might be good to have a friend on his trek, so he tells Toby. Toby immediately agrees to come. They plan to creep away while on leave the next day.
The Captain has given a large portion of the crew permission to head to shore for the day, which they all plan to do. Before they go, the Captain delivers a lecture about the dangers of the cannibal natives, but everyone still wishes to leave. The narrator hides some bits of bread, a piece of calico cloth, and some tobacco in his shirt. As they are heading to shore, it begins to pour. When they reach land, the shipmen take shelter under a bamboo covering. Waiting for the rain to stop, everyone but Toby and the narrator fall asleep. These two promptly flee the hut and start ascending the mountain. The rain has kept everyone indoors and although some natives spot them, Toby and the narrator can proceed. After only a few minutes, they are high enough to clearly see the bay below. Their climb grows difficult as the trail disappears. The narrator bushwhacks a path, but branches whip their flesh and they are sweating heavily. Finally, a few hours before sunset, they reach the desired mountain ridge. Standing on it, the highest part of the island, the narrator can see all the ships in the bay below. He feels complete exhilaration at their freedom and at the beauty around him.
From their spot on the mountain, the narrator expects to see the valleys of Typee and Happar behind them, but instead he only sees elevated land. He begins to wonder how they will survive as they are hiding. He and Toby decide to assess the supplies that they brought. The narrator's bread has melted away in the rain, but he still has the calico and tobacco. Toby hid two biscuits in his shirt that morning, but they now have become an amorphous blob of yeasty flour covered with strands of tobacco. Despite its inedible appearance, the men decide to share the food equally, starting the next morning. They erect a temporary shelter in a nearby ravine for the night, but it fails to keep out the pouring rain. By morning, they have scarcely slept due to the wet and cold. They wander in order to gather warmth. When another rainstorm appears, they hide under some bushes and Toby promptly falls asleep. Watching him, the narrator decides that they are like two babes in the wood. He also realizes that his leg has become injured, possibly from a snakebite. He gets up and sees that they now are above a beautiful valley. The sight is so spellbinding that he feels overjoyed.
Waking Toby, the two men gaze into the valley and begin to wonder whether the Happars or the Typees live there. Toby promptly determines that it is the Happar valley and decides that they should go there right away, since the Happars are friendly with Europeans. The narrator is skeptical. He fears falling in with the Typees. Because of his fear, they resolve to hike around the elevated land a little longer to search for another valley. Their hike is grueling as they are tired and hungry. The next morning they eat the last small portions of their bread ball. Being now hungry, tired, cold, and injured (in the case of the narrator), they decide to head into the valley, regardless of whether it is Happar or Typee, because they truly need nourishment and shelter.
The adventure is preceded by a lecture from the captain that accurately foreshadows some of the troubles that the narrator and Toby will face. The crew dismisses this lecture as another one of the captain's tricks to deny them their liberty. We might initially dismiss it as well, since we know that the captain is a villain. Still, the captain's warnings essentially prove prescient, as the narrator soon finds himself living amongst cannibal natives who want to tattoo him.
Not too long after Toby and the narrator get out into the world, one gets the impression that the men are poorly prepared for their adventure. They have brought no warm clothes or bedding to sleep in. They brought almost no food, except what is now a disgusting ball of wet bread. Their dreams of bedding down in comfortable native groves while munching on tropical fruit now seem ridiculously romantic. They are wet, cold, and desperate. They no longer appear to be brash, adventurous men, but rather young, romantic fools. The narrator's description of them as "babes in the wood" is fitting, since in this unknown environment they have become like children who need to rely upon other people (the natives) in order to survive. The motif of childhood and regression to a state of dependency shall recur as the book continues. As the men head deeper into the valley, the narrator in particular becomes more childlike. This motif continues Melville's comparison of the European and Polynesian worlds, suggesting that the Europeans, like these two men, are not superior to the natives, because they can scarcely survive in a natural landscape—the setting in which man originally was meant to be. The regression that the narrator goes through shall be an integral part of his entry into the valley.