Cities are at the centre of the debate to mitigate climate change. A considerable number of cities have already made commitments to sustainability transitions through the introduction and integration of green strategies. Moreover, in the past few years, Europe has witnessed an increase in the development of smart cities and advancement towards creating more sustainable cities. At the moment, an innovative concept in smart city development involves Positive Energy Districts (PEDs) that further encourage districts and cities to become carbon neutral. This paper looks at the five cities of Maia, Reykjavik, Kifissia, Kladno and Lviv that are a part of an ongoing H2020 project. The purpose of the paper was to understand the status quo of energy transition in these five cities as they embarked on the PEDs journey and identify associated challenges and benefits that PEDs brought to each city. The information was collected through a knowledge gap survey, City Vision 2050 workshop, discussions during the City Forum and individual interviews with city representatives. Cities across Europe and beyond may find themselves in a similar situation, and therefore, this paper also provides brief set of checkpoints to prepare new cities for the PED journey, thus enabling them to transition towards PEDs more efficiently.