Taking as a case the art-led regeneration of the derelict district of Lakkos in Heraklion town (Crete), the purpose of this exploratory study is to add to the knowledge of art produced by travelling artists as an important part of the town’s tourist offer by offering a rich contextual analysis of the mural images they produced and giving priority to their views. It adopts three data collection methods, photographic documentation (25 mural images), observations, and asynchronous email interviews with 21 traveling artists. By applying a typology in the main theme of each mural and by using travelling artists’ narratives three main groups of murals emerged, namely heritage-inspired, place-inspired and socially-inspired. The data collected are discussed in relation to the problems accrued from the gentrification of Lakkos through mural-based development. Due to limited past research, the typology that emerged from this study is only applicable to the case under study.