A wakefulness maintaining apparatus includes: an awakening stimulation controller that controls an awakening stimulation device to generate a cold air wind for maintaining a wakeful state of a target person; and a characteristic feature specification unit that specifies a characteristic feature of the target person. The awakening stimulation controller changes an air wind stimulation condition based on the characteristic feature of the target person specified by the characteristic feature specification unit. The air wind stimulation condition includes at least one of a region of the target person which the cold air wind generated from the awakening stimulation device hits, an air volume of the cold air wind, a temperature of the cold air wind, and an air blowing period of the cold air wind.