This essay shows how the institution of punishment by criminal transportation was entangled with the aesthetics of sublime transport introduced into English literary parlance by Boileau’s 1674 translation of Longinus’ Peri Hypsous, which would later become, in English, On the Sublime. Through readings of two early-eighteenth-century literary touchstones in the narration of criminal transportation—Daniel Defoe’s Moll Flanders (1722), and John Gay’s Polly (1729)—the essay argues that the tension between transport and transportation in these texts reveals emerging literary-critical anxieties about “modernity” and the perceived arrival of contemporary economic limitations on the aesthetic and ethical features of the sublime. Within early-eighteenth-century literary engagements with transportation emerge possibilities of a resistance to or a reappropriation of this commodification through the transporting capacities of literary form.