This Element will reevaluate the relationship between monasticism and the city in late antiquity and the early Middle Ages in the period 400 to 700 in both post-Roman West and the eastern Mediterranean, putting both of those areas in conversation. Building on recent scholarship on the nature of late antique urbanism, the authors can observe that the links between late antique Christian thought and the late and post-Roman urban space were far more relevant to the everyday practice of monasticism than previously thought. By comparing Latin, Greek and Syriac sources from a broad geographical area, the authors gain a birds' eye view on the enduring importance of urbanism in a late and post-Roman monastic world.