Notions of a learning city or learning region have captured the imagination of countries across every continent. In Africa, however, the implementation of this idea has been stubbornly sluggish. This chapter explores the ideology and rationale for learning cities with reference to the idea′s rapid evolution during the new millennium and the multitude of practical examples from around the world. The African context is discussed in relation to literature that has so far emerged from the continent. The chapter starts with some reflections on early, but abortive attempts to develop learning cities and regions in southern Africa and some of the reasons why these efforts have apparently not succeeded. It concludes with some lessons learned from the wider literature and the potential applicability of those lessons for Africa.