The Gymnasium was one of the key monuments for the formation of urban space and identity in Greek culture, and its transformation was closely interlinked with changing concepts of cityscaping. Knowledge as well as transfer of knowledge, ideas and concepts were crucial for the spread and long-lasting importance of gymnasia within and beyond the Greek and Roman world. The contributions investigate the relationship between gymnasia and cityscapes in the Hellenistic and Roman Imperial period as well as in the eastern and western Mediterranean, revealing chronological (dis)continuities and geographical (dis)similarities. The focus in the much-neglected west is on Sicily and South Italy (Akrai, Cuma, Herculaneum, Megara Hyblaea, Morgantina, Neaiton, Pompeii, Segesta, Syracuse), while many major sites with gymnasia from the entire eastern Mediterranean are included (Athens, Eretria, Olympia, Pergamon, Rhodes). Central topics comprise the critical reevaluation of specific sites and building types, the discussion of recent fieldwork, the assessment of sculptural decoration, and new insights about the gymnasiarchy and ruler cult in gymnasia.