This chapter delves into the notion of the learning city as an aspirational construct, rather than a fixed depiction of existing urban environments, and it raises the question of whether the learning city continues to be a social and political goal that is actively pursued. The global expansion of learning cities, as demonstrated by initiatives such as the PASCAL EcCoWell Cities programme and UNESCO’s International Learning City platform, indicates a gradual yet perceptible manifestation of the envisioned concept. However, it is important to exercise caution to avoid reductionist methodologies that favour utilitarian learning objectives, thus jeopardising the long-term viability of the system. This study ultimately contributes to the academic discourse on learning cities by investigating their evolution and complexities, with an emphasis on the progress of learning cities in Italy. Particular attention is directed towards the city of Lucca, with a focus on its political development, obstacles, and possibilities.