Urbanization increases imperviousness and reduces infiltration, retention, and evapotranspiration, frequently aggravating urban flooding due to greater runoff and higher and faster discharge peaks. Effective strategies to mitigate flood risks require a better understanding of the watershed dynamics and space to reverse the negative impacts. However, often cities do not have proper data sets to feed mathematical models that would be helpful in mapping water dynamics. Attempts to reduce flood risks have been made for decades by means of structural interventions but were frequently designed within the logic of a local scale, using limited available spaces and often merely shifting flooding downstream. Therefore, assessing urban floods requires a modeling approach capable of reflecting the watershed scale, considering interactions between hydraulic structures and urban landscape, where best practices and non-structural measures aim to improve community flood resilience through the reduction of social and financial costs in the long run. This paper proposes an integrated approach to analyze low impact development (LID) practices complemented by non-structural measures in a case study in southern Italy, supported by mathematical modeling in a strategy to overcome a context of almost no available data and limited urban open spaces.