An information system comprising: an in-vehicle terminal that is mounted on a vehicle, the in-vehicle terminal including a running history acquisition unit that acquires a running history of the vehicle; a communication unit that transmits the running history acquired by the running history acquisition unit to the server in association with a driver of the vehicle and receives driving assistance information distributed from the server; and a driving assistance unit that performs driving assistance of the driver according to a driving skill-level of the driver for each of driving skill elements, based on the driving assistance information received by the communication unit; and a server that communicates with the in-vehicle terminal, the server including a running history database in which a running history of the vehicle, received from the in-vehicle terminal, is stored for each driver, a driving skill-level determination unit that determines a driving skill-level of the driver for each of driving skill elements, based on the running history stored in the running history database and a driving difficulty level predefined for each driving skill element, a driving skill-level database that stores, for each driver, the driving skill-level determined for each of the driving skill elements by the driving skill-level determination unit, and a distribution information control unit that distributes to the in-vehicle terminal driving assistance information based on the driving skill-level stored in the driving skill-level database. an in-vehicle terminal that is mounted on a vehicle, the in-vehicle terminal including a running history acquisition unit that acquires a running history of the vehicle; a communication unit that transmits the running history acquired by the running history acquisition unit to the server in association with a driver of the vehicle and receives driving assistance information distributed from the server; and a driving assistance unit that performs driving assistance of the driver according to a driving skill-level of the driver for each of driving skill elements, based on the driving assistance information received by the communication unit; and a running history acquisition unit that acquires a running history of the vehicle; a communication unit that transmits the running history acquired by the running history acquisition unit to the server in association with a driver of the vehicle and receives driving assistance information distributed from the server; and a driving assistance unit that performs driving assistance of the driver according to a driving skill-level of the driver for each of driving skill elements, based on the driving assistance information received by the communication unit; and a server that communicates with the in-vehicle terminal, the server including a running history database in which a running history of the vehicle, received from the in-vehicle terminal, is stored for each driver, a driving skill-level determination unit that determines a driving skill-level of the driver for each of driving skill elements, based on the running history stored in the running history database and a driving difficulty level predefined for each driving skill element, a driving skill-level database that stores, for each driver, the driving skill-level determined for each of the driving skill elements by the driving skill-level determination unit, and a distribution information control unit that distributes to the in-vehicle terminal driving assistance information based on the driving skill-level stored in the driving skill-level database.