As both dream and desire, the occupation of the air — flight — possesses universal, archetypal significance. At virtually every time and in nearly every place in human history, cultures across the globe have endowed flying with symbolic, metaphorical, and mystical meanings. Today, in Europe, the USA, and throughout the Western world, the myth of Icarus is regarded as the touchstone in understanding the “meaning of flight.” A symbol and statement of the power of personal liberation (and its tragic cost), Icarus dominates Western consciousness and the popular culture. But the “Icarus myth” is itself a myth (and a relatively recent one at that). By way of describing the evolution of the modern “idea of flight” our first “Destination” takes us from the temperate isles of ancient Greece to the frozen steppes of medieval Russia (with several stops in between). Thereafter, we examine the first systematic (and scientific) attempts to come to terms with the nature of the heavens in the cosmology of pre-Socratic philosophers. Our investigation then turns to to the fanciful flying devices imagined by a Renaissance genius before culminating in a description of humankind’s first physical occupation of the heavens via the lighter-than-air craft contrived by two eighteenth-century French paper makers — and the showmen and charlatans who profited in their wake.