This paper investigates Herman Melville’s quest for spiritual stability and certainty in his novel Moby-Dick. The analysis establishes a philosophical tradition of doubt towards the Bible, outlining the philosophies of Thomas Hobbes, Benedict de Spinoza, David Hume, Thomas Paine and John Henry Newman. This historical survey of spiritual uncertainty establishes the issue of uncertainty that Melville writes about in the nineteenth century. Having assessed the issue of doubt, I then analyze Melville’s use of metaphorical charts, which his characters use to resolve this issue. Finally, I present Melville’s philosophical findings as he expresses them through the metaphor of whaling. Here, I also scrutinize Melville’s depiction of nature, as well as his presentation of the dichotomy between contemplative and active questing, as represented by the characters Ishmael and Ahab.