Aspects of the disclosure relate to a system and method for electronically monitoring and using data indicative of driver characteristics based on sensors. For example, the system may determine an origin associated with a user, a destination associated with the user, and a desired arrival time at the destination. A driving characteristic computing device of the system may determine an estimate for a duration of a trip from the origin to the destination. Based on the estimate for the duration and the desired arrival time at the destination, the driving characteristic computing device may determine a recommended departure time from the origin for the user. Based on sensor data, the system may determine a departure time from the origin for the user. The driving characteristic computing device may compare the departure time to the recommended departure time, and a value of a property of insurance for the user may be determined based on the comparing.