Electric bicycles and motorcycles have emerged as a possible way of improving the transportation system sustainability. This work’s aim was to quantify the energy consumption, the trip travel and the driving dynamics on specific routes in Lisbon, Portugal. Six electric and conventional bicycles and motorcycles were monitored, and a methodology to quantify the power required in each driving second was developed: Motorcycle and Bicycle Specific Power (MSP and BSP respectively). MSP and BSP allows characterizing energy consumption rates based on on-road data and to define real-world operation patterns (driving power distribution), as well as to benchmark the different propulsion technologies under the same baseline of specific power. For negative MSP and BSP modes, the conventional and the electric motorcycles and bicycles demonstrated a similar pattern. However, their behavior was different for positive modes, since electric technologies allow reaching higher power conditions. The methodology developed estimates accurately the energy consumption (average deviation of −0.19 ± 6.76% for motorcycles and of 1.41 ± 8.91% for bicycles). The MSP and BSP methodologies were tested in 2 Lisbon routes. For the electric motorcycle an increase in trip time (+36%) was observed when compared to the conventional one, while for the electric bicycle a 9.5% decrease was verified when compared to the conventional one. The Tank-to-Wheel (TTW) energy consumption for motorcycles was reduced by 61% when shifting to electric mobility, while a 30% Well-to-Wheel (WTW) reduction is obtained. For the electric bicycles, an additional energy use is quantified due to the battery electricity consumption.