Currently, there is a growing consensus that the use of more sustainable urban freight transportation has the potential to offer major energy and efficiency benefits which can be achieved through the appropriate combination of cargo bikes and the integration of drones into the urban logistics system. This study presents the results of a stepwise regression analysis that examines the role, benefits, and impact of electric vehicles such as e-bikes, cargo bikes, and drones for intermodal freight transportation in five Greek cities to support the green logistics paradigm. The results show that between routes of almost equal length, the most bicycle-friendly routes, such as routes along pedestrian areas or residential streets, should be avoided, as they reduce delivery speed and increase delivery costs in terms of energy and time expenditure. In addition, priority roads, which usually have higher traffic speeds and more trucks, are preferred by cyclists due to the quality of the road surface, even though the feeling of safety is lower on such roads. Finally, regarding drones, energy consumption is relatively low in the 0–5 mph and 6–10 mph wind speed ranges, indicating efficient energy use. In the 11–15 mph and 16–20 mph wind speed ranges, energy efficiency is significantly lower than the battery capacity, indicating that the cargo drone exhibits excessive energy consumption under these conditions.