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The development of electric vehicles (EVs) as part of the electrification of the transportation sector plays a significant role in energy transition to a low-carbon and highly renewable society. The use of EVs has been promoted through the development of inclusive strategies for electromobility in the recent years. Apart from actions directed and funded by the European Union, national strategies have also been employed to support electromobility. Such a strategic plan has already been enacted by the Hellenic Ministry of Environment and Energy, funding municipalities to prepare siting and sizing plans for electric vehicle chargers. In this paper, the final study of this strategic plan for the municipality of Heraklion in Crete is used as a case study to investigate the effect of EV chargers on the operation of the Cretan power system. Their selected siting points are evaluated by performing a power flow analysis at the level of 150 kV. Thus, they are aggregated in each 20 kV/150 kV distribution substation of the electrical grid with the aim of investigating their effect on substation loading and transmission line losses. Generally, extensive fast charging should be avoided to minimize the risk of sudden stress of the existing cities' grids and control strategies should be implemented to mitigate the need for upscale substation equipment or even postpone reinforcements. [ABSTRACT FROM AUTHOR]