It has been conjectured, but on insufficient evidence, that the Phoenicians discovered Madeira at a very early period. Pliny mentions certain Purple or Mauretanian Islands, the position of which with reference to the Fortunate Islands or Canaries might seem to indicate Madeira islands. Plutarch (Sertorius, 75 AD) referring to the military commander Quintus Sertorius (d. 72 BC), relates that after his return to Cadiz following a military reverse in Mauretania, "he met seamen recently arrived from Atlantic islands, two in number, divided from one another only by a narrow channel and distant from the coast of Africa 10,000 furlongs. They are called Isles of the Blest." The estimated distance from Africa, and the closeness of the two islands, seem to indicate Madeira and Porto Santo.
There is a romantic story, of doubtful truth, to the effect that two lovers, Robert Machim and Anna d'Arfet, fleeing from England to France in 1346, were driven off their course by a violent storm, and cast on the coast of Madeira at the place subsequently named Machico, in memory of one of them. On the evidence of a portolan dated 1351, preserved at Florence, Italy, it would appear that Madeira had been discovered long previous to that date by Portuguese vessels under Genoese captains.
In 1419 two of the captains of Prince Henry the Navigator, João Gonçalves Zarco and Tristão Vaz Teixeira, were driven by a storm to the island called by them Porto Santo, or Holy Port, in gratitude for their rescue from shipwreck. The next year an expedition was sent to populate the island, and, Madeira being described, they made for it, and took possession on behalf of the Portuguese crown.
The islands started to be settled circa 1432 or 1433. In September 23, 1433, the name ILHA DA MADEIRA (Madeira Island or "island of the wood") appears in a map, by the first time, in a document.
In 1921, the Austro-Hungarian Emperor Charles I was deported to Madeira, after an unsuccessful coup d'état. He died there one year later.
In 1976, following the democratic revolution of 1974, Portugal granted autonomy to Madeira.