The general thesis of this contribution is that metropolitan cities—mostly port cities, also characterized most of the time by a relevant historical-architectural landscape—can reduce their agglomeration diseconomies if they adopt a ‘circular’ model of organization. The ‘territorialized’ model of circular economy is the ‘circular city’ model, which puts its centre with its suburbs, its historical centre with the port, and the consolidated city with the suburban territory in virtuous relationships. This chapter focuses on the multidimensional benefits of the circular economy and circular city model from an evaluation perspective, identifying an analytical list of indicators emerging from operational practice and the scientific literature. A multidimensional and multicriteria assessment method is used in the metropolitan city of Naples, Italy, to support the planning process for development of the port area from the perspective of the circular economy and circular city model. The originality of this assessment consists, on the one hand, in assuming evaluation criteria emerging from the strategy of the European Green Deal and, on the other hand, in focusing on the integration of the indicators proposed by the World Health Organization related to the Health Impact Assessment in a perspective that integrates environmental, economic and social impacts assessments.