In his youth, Richard Henry Dana Jr. rebelled against the conventions of his upper-class New England upbringing when he signed on as a common sailor on a merchant ship bound for Alta California. The notes of his travels describe the strenuous life at sea, a captain’s sadistic streak, a crew’s mutinous tendencies, and California’s multicultural fur trade economy. First published in 1840, Dana’s travelogue Two Years Before the Mast became an unofficial guide for emigrants traversing the largely unmapped far western territories in the wake of the Mexican-American War. Connecting Dana’s widely-read narrative to current developments in the discipline, this article discusses strategies of visualizing literature and includes an exercise in ‘discursively mapping’ actual and imagined spaces and mobilities of the text. Considering strategies and toolsets from the digital humanities as well as theories such as Lefebvre’s concept of representational space, the article reflects on the methodological and practical pitfalls brought about by the visualization of spatial imaginations as part of a more digitally literate and spatially conscious American Studies.