This paper explores, from a multidisciplinary viewpoint, some of the most important questions relating to the management of heritage systems on the territorial scale, such as historic cultural routes, with specific reference to the vision and approach of UNESCO. In fact UNESCO World Heritage (Batisse, Bolla 2005), which now counts more than 1000 listed sites, is facing a significant transition both in terms of its recognition procedures and of management tools, particularly with regard to the challenges posed by the 2030 Sustainable Development Agenda. Aside from the administrative aspects, which strictly depend on specific national regulations, there are other management issues of which heritage organisations should be aware and that they should be ready to question.