From Story Mode, press Options to open the menu and press left. This takes you to Rockstar Editor. Enter this and select Director Mode (you need to be on foot, with no cops on you, outside and not have a wanted level for this option). Pick any Actor you want and it will load into Director Mode.
Hold the Touch Pad to bring up options, one of those is location. The first location you should pick is the airport. Once you load there, repeat and go to the next location in the list. Keep doing this until you reach the last location and unlock the trophy