The research presented in the work is linked to important production of data over 10 years of activity that allowed us to trace the configuration of Italian urban settlements in the 1950s. Starting from this information, the paper puts forward a uchronian reconstruction of the physiognomy of the national territory asking if—instead of the weak urban development policies implemented for over half a century—a more purposeful method of planning and designing settlements had been chosen in the Sixties to favor their aggregation and protect the country’s huge landscape heritage. From the model used, important indications emerge for control and management of retrofit (de-sprinkling) policies of which the need has been felt in recent years, as suggested by repeated messages from European bodies, the scientific community, associations and some politicians. The uchronic scenario is constructed starting from the settlement configuration of the 1950s, developing a model of maximum aggregation for the urbanized parts that were intervened in between this period and 2000, simulating a geography that maintains the quantities of soil transformed over the last 50 years. It emerges from the processing of the data that the Italian territory would have retained its low settlement density areas almost intact at the same level as in the 50s, that is to say 73% of the entire peninsular territory. It would also have preserved a large part of its free peninsular and insular coastline at about 60–70%, against the present day 45%.
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