Since its creation in the 1990s, the concept of a digital city has greatly evolved: moving from a mere digital conception to a specific territorial approach that focuses on the interconnections between the digital and the physical. Portuguese digital cities are an example of this evolution, as they are currently developed, mainly in a local e-government structure aiming to enable local actors to embrace sustainable development, the exercise of citizenship and the formation of a knowledge society. This paper discusses the study of two Portuguese digital cities, in light of the emerging concept of intelligent cities. But questioning whether a digital city can be considered intelligent. We conclude that digital cities contribute to the development of the urban/regional intelligence, therefore setting the ground for a more advanced city based on participation, learning, innovation, creativity and competitiveness.