Italy, as an EU member state, is subject to the Macroeconomic Imbalances Procedure. The aim of the paper is to evaluate the development of the external macroeconomic imbalances of the Italian economy, as well as its synchronization with other EU countries, between 2013 and 2022. The required results are obtained using the furthest neighbor agglomerative method of cluster analysis, with the resulting dendrogram. The main conclusion to be drawn from the cluster analysis is the identification of a significant long-term mutual similarity in the development of external macroeconomic imbalances in Italy and France, as well as with core EU countries in 2014, 2017 and 2022, but not in 2020. Both countries experienced similar structural problems, including labor market mismatches, persistent structural unemployment, and low cost competitiveness of the corporate sector, high income inequality, and large redistributive programs that were offset by fiscal deficits. Throughout the period under review, Italy experienced significant negative changes in its export market share. This was mainly due to increased labor costs, declining labor productivity, the Italian economy’s strong dependence on tourism, and the impact of the Covid-19 pandemic, escalating inflation levels and rising energy prices. This information can be an important indicator for early warning of adverse economic developments.