Learning cities and learning regions are concepts closely interrelated and based on European initiatives and concepts of lifelong learning (Osborne et al., International Review of Education 59(4): 409–423, 2013). As the conceptualisation of lifelong learning in national contexts has taken different shapes, the same can be stated for the concepts of learning cities and learning regions that have been developed from the late 1990s on (Longworth & Osborne, 2010). Our chapter takes stock of the initiatives of learning regions and learning communities in Germany and provides a counter-narrative of the Hamburg Open Online University (HOOU) that could be perceived as a future oriented vision of a learning city, re-vitalising some of the ideas encapsulated in the concept of learning cities and including some transformative elements. Therefore, we analyse the HOOU against the framework of key features of learning cities from UNESCO (UNESCO Global Network of Learning Cities—Guiding documents, UNESCO Institute for Lifelong Learning, 2015) and provide an outlook on paths that could be taken.