This exploratory study explored the factors underlying the perceived driving difficulties of older drivers with mild cognitive impairment (MCI) in comparison with controls of similar age, using an extensive questionnaire to assess their relative importance. Each group reported distinct patterns of perceived difficulties, indicating driving situations which may warrant special attention on the part of road designers and road safety engineers. Consideration of challenging driving situations might also have a role to play in the design of fitness-to-drive assessment tools, training programs, and/or vehicle technologies for older drivers.