Caution is a second-generation ace pilot desperately trying to bury his past and the memories of his father— a daredevil barnstormer who perished trying to wow crowds and killed Caution's mother from the shock. Now Caution has worked his way up the ladder as an ultra-efficient, ultra-conservative general manager of a small airline struggling to make ends meet. When the US Post Office puts its international delivery service up for grabs to the first airline that can successfully circumnavigate the globe and outperform every other airline, Caution's boss presses him into competing for the contract. Against his better judgement, Caution throws his name to the wind, risking the hazards of the round-world air race. Joined by a fiery blonde stunt flyer as his female co-pilot, he begins the journey only to discover that a rival airline is trying to sabotage their every move.