The paper, through the study of the main maps and historical imagery, intends to describe through pictures  the fortified city of Gallipoli alongside the evolution of the Mediterranean coastal landscape  and, specifically of the Salento peninsula. Starting from the analysis of the Piri Reis map, a specific selection of depictions shows how the city with its castle, its fortifications and its ancient port overlooking the Ionic coast, was always identified as territorial landmark; it has been geographically recognizable since the first maps and views, both for the structure intended to protect from incursions from the sea and for the commercial exchanges with other mediterranean countries. From the analysis of images made at different times and for different purposes, it appears that the Gallipoli has always been seen as a center of primary importance in the fortified coastal landscape, like it still are today. In spite of the progressive urban growth, the phenomena of conurbation and the transformations of the coasts caused by coastal anthropization remain fully recognizable in their original structure and in their inseparable relationship with the marine and terrestrial landscape.