There are records of people doing this as far back as the eleventh century: Oliver of Malmesbury, an English Benedictine monk studied mathematics and astrology, earning the reputation of a wizard. He apparently build some wings, modeled after those of Deadalus. An 1850's history of Balloons by Bescherelle describes the legend of his experiments. "Having fastened them to his hands, he sprang from the top of a tower against the wind. He succeeded in sailing a distance of 125 paces; but either through the impetuosity or whirling of the wind, or through nervousness resulting from his audacious enterprise, he fell to the earth and broke his legs. Henceforth he dragged a miserable, languishing exisitance, attributing his misfortune to his having failed to attach a tail to his feet."
In 1178, a 'Saracen' of Constantinople undertook to sail into the air from the top of the tower of the Hippodrome in the presence of the Emperor, Manuel Comnenus. The attempt is described in a history of Constantinople by Cousin, and recounted in several 19th century books on Aerial Navigation. "He stood upright, clothed in a white robe, very long and very wide, whose folds, stiffened by willow wands, were to serve as sails to receive the wind. All the spectators kept their eyes intently fixed upon him, and many cried, 'Fly, fly, O Saracen! Do not keep us so long in suspense while thou art weighing the wind!' The Emperor, who was present, then attempted to dissuade him from this vain and dangerous enterprise. The Sultan of Turkey in Asia, who was then on a visit to Constantinople, and who was also present at this experiment, halted between dread and hope, wishing on the one hand for the Saracen's success, and apprehending on the other that he should shamefully perish. The Saracen kept extending his arms to catch the wind. At last, when he deemed it favorable, he rose into the air like a bird; but his flight was as unfortunate as that of Icarus, for the weight of his body having more power to draw him downward than his artificial wings had to sustain him, he fell and broke his bones, and such was his misfortune that instead of sympathy there was only merriment over his misadventure."
In the late fourteenth century there are reports of partial success by
an Italian mathematician Giovanti Dante. He is said to have successfully sailed over
a lake, but then attempted to repeat the trick in honor of a wedding.
"Starting from the highest tower in the city of Perugia,
he sailed across the public square and balanced himself for a long time in the air.
Unfortunately, the iron forging which managed his left wing suddenly broke,
so that he fell upon the Notre Dame Church and had one leg broken. Upon
his recovery he went to teach mathematics at Venice."
According to Stephen Dalton, in The Miracle of Flight, "Four years later, John Damian, Abbot of Tungland and physician of the
Scottish court of King James IV, attempted to fly with wings from the
battlements of Stirling Castle." He is also not credited with being the first to fly.