Recently identified by the editors as the Rua Nova dos Mercadores, the principal commercial and financial street in Renaissance Lisbon, two sixteenth-century paintings, acquired by Dante Gabriel Rossetti in 1866, form the starting point for this portrait of a global city in the early modern period. Focusing on unpublished objects, and incorporating newly discovered documents and inventories that allow novel interpretations of the Rua Nova and the goods for sale on it, these essays offer a compelling and original study of a metropolis whose reach once spanned four continents.