Systems and methods for ranking routes based on driving complexity are provided. The systems and methods may generate routes for a user based on factors indicative of difficulty levels of the routes (for example, based on the types of road features that exist on the route, among various other factors). The difficulty levels of the generated routes may then be used to automatically select, by a navigation system of a vehicle, a route that is suitable for the user based on their driving experience level. Alternatively, the routes may be presented to the user via the vehicle or a mobile device for selection by the user. The systems and methods may also be dynamic in that the difficulty levels of the routes may be adjusted as the user gains more driving experience.