The paper explores the potentialities of telework, a topic with rich literature published since the 1970s, which has become topical again with its forced application related to the COVID-19 pandemic emergency. The paper carries out an analysis of the potential territorial impact—transport networks and geographies of living—of telework in the Italian national context. The analysis highlights the potential relevance of the application of telework in certain metropolitan areas that present urban poles where economic sectors with a high propensity for telework are centralised. This survey relates the large stock of tourist housing in the vicinity of large metropolitan areas to a potential demand arising from the change in housing preferences towards more pleasant contexts made possible by the application of telework. In conclusion, this work aims to contribute to the construction of a platform for the Italian context—lagging behind but with recent legislative measures on smart working—aimed at favouring the definition of research lines able to enhance the potential offered by the application of telework for environmental, social, and territorial sustainability objectives, and it also aims to outline possible territorial scenarios for the main metropolitan areas

This paper analyses the planning implementation conducted by the Lombardy Region, in two different inter-municipal realities, as a useful example in a local context: the Area Regional Territorial Plan Alpine Valleys and the Area Regional Territorial Plan of the Franciacorta geographical area. These two complex experiences suggest positive conditions for the implementation of policies of Urban-Rural/Mountain partnerships to reach common goals and enhance urban-rural relationships, and complex institutional/administrative frameworks for activating multi-level governance processes.