A dynamic navigation coach system is programmed to monitor and assist drivers while keeping them engaged en route to the destination. The system may provide driver navigation assistance and training that monitors user navigational skills, driving habits, and environmental factors, and provides dynamically adjustable tools to provide varying levels of navigation assistance in a game play format. The system may selectively provide navigational directions or corrections to the driver when the driver deviates from a scheduled travel route, instead of providing instructions at every driving event.