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The Italian National Strategy for Sustainable Development plays an important role in the national implementation of the 17 Goals for sustainable development set globally through the 2030 Agenda of the United Nations. The achievement of such goals in Italy is linked to the strategic choices and objectives established at the national level. The purpose of this work is to monitor the performance of the 20 Italian regions in 4 of the 5 areas of the Agenda (People, Planet, Prosperity, Peace) over a period of time ranging from the implementation of the National Strategy to the post-pandemic. To do this, a set of representative indicators was created and a geographical sustainability assessment tool (SSAM) was used, which operates through a multicriteria analysis model perfectly integrated into a GIS environment. The results showed a strong regional variability and a radicalized North-South gap. Moreover, the monitoring between the different years (2017-2019-2021) showed the initially positive impact of the strategy, mainly due to the Planet dimension, but also the negative one that COVID-19 caused to all the regions, with different intensity depending on the dimensions considered.