Is there a relationship between sustainability strategies and the financial efforts for their realization? This is a particularly complex question considering that sustainability has generated an intense academic and political debate. In order to contribute to the debate, the authors investigate the existence of the relationship between the strategies of local authorities in terms of sustainability and their translation into financial commitments. To this end, firstly, the paper shows the results of research that explores the sustainability strategies of a sample of the 20 Italian regional capital cities, through the content analysis of their Performance Plans. Secondly, the authors present their elaboration of financial data related to the main dimensions of sustainability (environment and territory management, welfare area, and economic development). Finally, they discuss the relationship between the two aspects surveyed (strategies and expenditures committed to sustainability) highlighting critical perspectives also for future research. Briefly, the conclusions underline: a) great autonomy in formulating strategies, highlighted by the different programming documents analyzed; b) the main terms related to sustainability are rarely used; c) particular importance, from a financial point of view, was given to the environmental and welfare sustainability dimensions both in relation to the total current expenditure committed, and in terms of financial implementation. The expenditure impact for economic development is much lower, while the average level of financial implementation of the same is higher; and d) a discrepancy between the limited strategic consideration of the sustainability dimensions and the considerable amount of financial commitments related to sustainability.