This dissertation studies interlocking representations of travel and drugs in contemporary American, British, and Canadian novels, exploring how those thematics alternately destabilize and assuage subjectivity, genre, and the perception of space. Following a prefatory chapter, Chapters Two and Three serve as a two-part introduction. The first part articulates a theoretical lens I designate by enclosing the word “tripping,” a colloquialism for a drug experience, in quotation marks. Through this lens, I examine travel and drugs in contemporary fiction indebted to sixties counterculture. In Chapter Three, I examine the work of William S. Burroughs and Aldous Huxley, contextualizing their mid-twentieth-century travel and drugs as foundational to later twentieth-century “tripping.” Chapter Four treats Huxley’s novel, Island, as a revision of the foundations I outline in the previous chapter; his instantiation and critique of utopia via “tripping” help conceptualize the psychedelic experience as protective spatial movement – physical mobility instead of psychedelic fungibility – in the service of preserving a stable sense of self. Chapter Five discusses Alex Garland’s The Beach, in which drugs reveals the limitations of utopian thought by underscoring the paradoxical notion of immobility hidden within the supposed freedom of mobility. In these novels, Huxley and Garland depict travel as a key to the process of rendering psychedelic intoxication knowable in familiar terms. Chapters Six and Seven, in exploring Hunter S. Thompson and Robert Sedlack, shift toward defamiliarizing conventional modes of travel using some of the radical possibilities of drug intoxication. Chapter Six examines Fear and Loathing in Las Vegas, a text which, instead of attempting to understand inassimilable drug experiences by spatializing the drugged mind, explores mind-alteration as a way of understanding the postmodern space of Las Vegas that emerges following the demise of the counterculture. Chapter Seven constructs a reading of Sedlack’s The African Safari Papers, examining ways its representation of self-conscious tourism, inflected by intoxication and Thompson-inspired excess, deploys the figures of the shaman and of animals to complicate conventional understandings of tourism. Thompson and Sedlack explore how the subjectivities of domestic and global tourists are reshaped by, rather than resist, the radical alterity introduced by the drug experience.