What follows will begin by introducing the two writers who are our subjects (Peter Martyr d'Anghleria and Francisco Cervantes de Salazar) before we consider their varied approaches to the indigenous settlements of the Caribbean and Mesoamerica. Their accounts of these villages and cities will then be contrasted with their depictions of Spanish urban foundations. This examination reveals how the Roman colonial city could be used to understand the cities of the New World and to model Spanish imperialism in these lands. This in turn demonstrates the usefulness of the ancient city as a tool for thinking about colonial cities in later centuries