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In this chapter, the focus shifts from ship to shore in order to explore metropolitan writing that captured the distinctive urban-littoral spaces of the Victorian port city. Forging connections between the urban ethnography of Henry Mayhew and Charles Booth, with accounts of ‘sailortown’ and its attendant ‘waterside characters’ in novels by Herman Melville (Redburn: His First Voyage), Charles Dickens (Our Mutual Friend), and James Joyce (Ulysses), this chapter reveals the urban waterfront to be an important edge space that functioned as both a working-class habitat shaped by waterside industry and an imaginative locus for a range of nineteenth-century writers. The analysis demonstrates that despite its physical location on the edge of the city, and its peripheral status within literary history, the watery city was a site for the production of new narratives of modernity at the turn of the twentieth century.