This thesis explores the spatial interplay between the harbour and the Medieval City of Rhodes, tracing how the Knights of St. John and the Ottoman Empire shaped the island’s urban identity. By adopting a spatial-historical methodology supported by cartographic reconstructions, the study demonstrates how military, religious, and economic priorities influenced the city’s structure over time. The fortified integration of the harbour under the Knights is contrasted with the Ottoman strategy of adaptive reuse and integration into imperial trade networks. The research reveals a persistent spatial logic that transcended regime changes, manifesting in fortified architecture and religious-military infrastructure. Through original maps and analysis of historical sources, the thesis argues that Rhodes developed not only as a strategic military outpost but as a spatial palimpsest reflecting layered ideologies of control and power. This study contributes to architectural history by offering a visual and analytical framework for understanding how imperial legacies shape urban morphology in the Mediterranean context.