The definition, characterization and implementation of Positive Energy Districts is crucial in the path towards urban decarbonization and energy transition. However, several issues still must be addressed: the need for a clear and comprehensive definition, and the settlement of a consistent design approach for Positive Energy Districts. As emerged throughout the workshop held during the fourth edition of Smart and Sustainable Planning for Cities and Regions Conference (SSPCR 2022) in Bolzano (Italy), further critical points are also linked to the planning, modeling and assessment steps, besides sustainability aspects and stakeholders’ involvement. The “World Café” methodology adopted during the workshop allowed for simple—but also effective and flexible—group discussions focused on the detection of key PED characteristics, such as morphologic, socio-economic, demographic, technological, quality-of-life and feasibility factors. Four main work groups were defined in order to allow them to share, compare and discuss around five main PED-related topics: energy efficiency, energy flexibility, e-mobility, soft mobility, and low-carbon generation. Indeed, to properly deal with PED challenges and crucial aspects, it is necessary to combine and balance these technologies with enabler factors like financing instruments, social innovation and involvement, innovative governance and far-sighted policies. This paper proposes, in a structured form, the main outcomes of the co-creation approach developed during the workshop. The importance of implementing a holistic approach was highlighted: it requires a systematic and consistent integration of economic, environmental and social aspects directly connected to an interdisciplinary cross-sectorial collaboration between researchers, policymakers, industries, municipalities, and citizens. Furthermore, it was reaffirmed that, to make informed and reasoned decisions throughout an effective PED design and planning process, social, ecological, and cultural factors (besides merely technical aspects) play a crucial role. Thanks to the valuable insights and recommendations gathered from the workshop participants, a conscious awareness of key issues in PED design and implementation emerged, and the fundamental role of stakeholders in the PED development path was confirmed.