Electric Vehicles (EV) adoption targets have been set by governments from countries throughout Europe, related to the European goals, for the decarbonization of the road transport sector. The change for electric vehicle technology can be challenging to EV users for a number of reasons such as battery autonomy, time to charge the vehicle, and the different driving conditions. The work in this paper aims to study how users from Madeira and Porto Santo islands deal with the challenges of EV adoption. Furthermore, this paper also studies the role of the orography in the Regenerative Braking System technology integrated into electric vehicles. To assess such information, an online questionnaire was prepared and sent out to the electric vehicle community of both islands. The main results of this study show drivers’ preference to charge the vehicles at their household and that users are satisfied with the vehicle’s technology. Also, users’ battery range anxiety did not seem to have a significant impact. Moreover, from the drivers’ point of view, there is still the need to study the role of orography, while using the regenerative braking system.