The first step was to create a list of all the places I have flown between at least once. Paging through my travel photos and diaries, I managed to create a pretty complete list. The structure of this document is simply a list of all routes (From, To) and every flight only gets counted once. The next step finds the spatial coordinates for each airport by searching Google Maps using the geocode function from the ggmap package. In some instances, I had to add the country name to avoid confusion between places.
The end result is imperfect (as Peter mentions, ggmap isn’t wrapping around), but does fit the bill for being eye-catching.