A transportation management system can maintain a set of driver logs for drivers operating throughout a given region, where each driver log indicates driving characteristics of a respective driver. The system can determine a destination for the respective driver operating a vehicle from an initial location to the destination, and determine a set of routes between the initial location and the destination. Based at least in part on the driving characteristics of the respective driver, the system can determine an individualized risk value for the respective driver for each route of the set of routes, and select an optimal route from the set of routes based, at least in part, on the individualized risk value for each route.