Few other localities, in the Mediterranean and beyond, can compete with the alluring literary reputation of the Strait of Scylla and Charybdis, the monsters from the Odyssey that have traditionally been associated with the marine passage between Calabria and Sicily. In Homer's account, Odysseus had to cross a narrow passage, on each side of which lurked a fearsome monster. The first, Scylla, was a six-headed predator whose waist was encircled by wailing, canine heads. The second, Charybdis, was a vast creature whose gaping maw could gulp mountains of water along with anything that sailed too close. 1 Homer did not provide a specific setting for the tale, but the vagueness of the epic poem and geographical clues gave rise to a tradition that identified the Strait as the setting of the myth. 2 By looking at modern written and visual accounts from the Grand Tour era, ranging from the many eighteenth to the early twentieth centuries, this chapter will illustrate how some European travellers viewed the relationship between the Homeric myth and the Strait. This relationship grew out of philhellenism and, often, from an urbanite perspective of lands they would have perceived as remote and timeless, uncontaminated by modernity and at once exotically beautiful yet subtly threatening. Focusing on a textual and visual analysis of these historical documents, this chapter traces a series of interrelated issues: first, the impact of the Greco-Roman literary tradition on inspiring reenactments of the voyage of Odysseus within the Strait. The South of Italy became the setting for erudite escapism and literary travel: within the region, striking sceneries co-existed with the disquieting rêverie of legends and myths. Second, the chapter will demonstrate how these monstrous-feminine creatures were seen to allegorize the marvels and dreads of an area characterized by