The relationship between rivers and cities has evolved from a natural coexistence and interdependence to a progressive relationship of segregation and disintegration. This article uses a planning experiment to explore and discuss some concerns about visual attractiveness of city–river landscapes in promoting spatial integration of cities and rivers. It presents a methodological approach integrating expert opinions and public perception questionnaires. This is a contribution to making operational an ongoing aesthetic assessment of different dimensions and viewpoints at the city scale. This approach is illustrated with a case-study in the Lisbon metropolitan area and its main assessment results are integrated in a city–river profile that can be useful in ongoing evaluation processes of river landscapes and urban planning practice.