Leonardo Da Vinci's painting The Annunciation, which I recently saw in the Uffizi gallery, apart from being a stunning painting, was also a painting of a prototype for flying. Leonardo was basing his ideas on the legend of Daedalus who flew with wax wings which melted when he flew too close to the sun. Leonardo was considering the scientific possibility of a man flying and represented it in this painting. His notebooks are also full of drawings of machines using bat-like wings to fly. See this article in the Guardian which discusses the idea in more detail.