Renewable energy communities (RECs) aim at achieving economic, environmental, and social benefits for members and for society. This paper presents a roadmap for the design, operation, and monitoring of renewable energy communities in Italy, fundamental to guide and orient any stakeholder involved in the decision-making process of a REC. The roadmap is inspired by the Deming Cycle, also known as Plan-Do-Check-Act, which provides a framework for continuous improvement and standardization of the procedures. To demonstrate the practical application of the roadmap, a real case study is presented for Italian energy communities, making full adoption of data derived from official databases and using a real urban district as a case study. The findings of phase I in the “do” stage of the roadmap indicate that the REC could lead to a decrease in carbon emissions of roughly 38% and could support 51 to 67 families through REC’s revenues, depending on the installed PV capacity. Furthermore, both physical self-consumption and virtual self-consumption schemes assist in the sustainable transition of the built environment, where consumers have a significant impact on the electrical markets. Therefore, these results validate the roadmap’s effectiveness in promoting an informed design and implementation of RECs while guiding energy, social, and political decisions.