Although older people are regulating their driving spontaneously as a compensation strategy for driving abilities changes, seasonality of driving habits might be associated with self-regulation of driving of older drivers. This study investigates driving habits and preliminary destination analysis from the GPS data on private vehicles of older people to discuss the usual self-regulation of driving and the present regulation. For driving habits, driving distance and frequency in January and February decrease compared to the other months, and the decrease is associated with uncontrolled external factors as climate conditions (temperature). A destination analysis of February indicates that the “other” category such as a private house, office building, station, where associated with a specific and individual purpose, decreased in contrast to the results of April. Older people may self-regulate visits family, the community, and social interests while maintaining essential activities in the present situation.