Provided is a driving assistance apparatus that assists driving of a vehicle. The driving assistance apparatus includes: a training data generator that stores a traveling route traveled by the vehicle according to a driving operation of a user in a training traveling mode, and generates training data for a target route based on the traveling route. The training data generator generates the target route by connecting, for example, between a first point and a second point on the traveling route, in a case where a difference in orientation of the vehicle at the first point and the second point during training traveling is less than a first threshold and distance between the vehicle at the first point and the vehicle at the second point during the training traveling is less than a second threshold.