A system for automatically constructing a flight plan that aligns with a boundary line is provided. The system has a controller that is configured to: automatically select a set of geographical (geo) coordinate waypoints along a boundary line using waypoints from the geographical database responsive to flight crew input; refine the set of geo coordinate waypoints using a calculated turn initiation distance and a turn completion distance for every waypoint; further refine the refined set of geo coordinate waypoints based on the course change between waypoints; generate a set of courses and distances between waypoints through computing, for each set of two consecutive waypoints in the further refined set of geo coordinate waypoints, the course and distance between the two consecutive waypoints; and construct the flight plan based on the waypoints in the further refined set of geo coordinate waypoints and the set of courses and distances between waypoints.