Navigation system having maneuver attempt training mechanism and method of operation thereof

A method of operation of a navigation system includes: generating a maneuver instruction for a driving maneuver, the maneuver instruction including an explanation of how to turn, merge, park or operate a driver's vehicle; monitoring a maneuver attempt for a compliance to the maneuver instruction; modifying the maneuver instruction based on the maneuver attempt; assigning a driver skill grade for the maneuver attempt based on the compliance to the maneuver instruction; and generating a training feedback to improve the driver skill grade of the maneuver attempt for displaying on a device.