The PNRR represents an unprecedented opportunity for urban regeneration and territorial planning in Italy, particularly at the municipal and metropolitan levels. Despite controversies related to its design, management, and fund allocation, it has allowed cities to complete complex projects and innovate governance structures. However, challenges remain, including an imbalance in funding distribution favoring capital cities and a lack of a clear regulatory framework for metropolitan governance. The research highlights how the plan has redefined the role of Metropolitan Cities (MCs), positioning them as intermediaries between national and local scales. The MC of Bologna has played a coordinating role, consolidating local proposals into three major projects focusing on mobility and housing. In contrast, the MC of Florence adopted a thematic approach, emphasizing accessibility, sustainability, and housing inclusivity. The PNRR’s interventions have reinforced MCs’ strategic planning functions while also challenging their governance structures. This shift has implications for the interaction between municipal, metropolitan, and national planning, shaping the future of urban regeneration in Italy.