Port cities and coastal towns represent specific settlements in which the mutual relationship between communities, economic activities, and use of marine and natural resources is evident. Such tension has led to a rich cultural and landscape heritage stratification along the coast and the consequent recognition of its intrinsic value. On the contrary, the out-of-control expansion of settlements and infrastructures, as well as the extractive dynamics of the industrial-type economy, have threatened and endangered the coastal ecosystem within the balance of its anthropic and natural assets. Tourism represents a vital development driver and an opportunity for an economic shift in southern Mediterranean coastal areas; however, by re-proposing the same territorial exploitation logic based on land consumption, pollution, and economic disparity, tourism can generate unsustainable regional development. The evidence from the literature helps characterize sustainable development for tourism, which was then investigated, as well as the tourism and cultural policies of the Puglia Region, where tourist uses of the coastal heritage are particularly evident. The coastal planning tools adopted in Puglia were examined to explore the relationship between tourism development’s effects and the territory’s specific features and coastal landscape. The results make it possible to define guiding criteria for the monitoring and ex-post evaluation of the impacts of tourism and cultural planning in coastal and port cities, integrating evaluation into public decision-making processes.