Traffic-calming measures (TCMs) are non-invasive devices designed to improve road mobility and urban areas on a human scale. Despite their potential, they have been in use for a long time and now have to deal with the latest technological innovations in the automotive field, such as cooperative driving technologies (CDTs), to improve energy efficiency in cities. The goal of this study is to explore the safety and operational performances of TCMs featuring CDTs in urban areas. An urban-scale road network close to a seaside area in the City of Mazara del Vallo, Italy, was properly redesigned and simulated in AIMSUN to assess several design solutions, where connected and automated vehicles (CAVs) have been employed as a more energy-efficient public transportation system. Preliminarily, the fine-tuning process of model parameters included CAVs and human-operated vehicles (HOVs) flowing through the network up to saturation conditions. The safety of the planned solutions was tested by using surrogate measures. The micro-simulation approach allowed us to know in advance and compare the operational and safety performances of environmentally friendly solutions involving TCMs and CDTs. These results can also support urban road decision makers in pivoting urban-traffic-calming-based design solutions featuring cooperative driving technologies toward energy efficiency transitions for smart cities.