The history of Madeira begins with the discovery of the islands by Portugal in 1419. There is no record of anyone living on the islands at that time. Portugal began colonizing the island in 1420.
Pre-Portuguese times
Pliny mentions certain Purple Islands, the position of which with reference to the Fortunate Islands or Canaries might seem to indicate Madeira islands. Plutarch referring to the military commander Quintus Sertorius , relates that after his return to Cádiz, "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, which is much smaller than Madeira itself, and to the north east of it.

Tenth- or eleventh-century fragments of mouse bone found in Madeira, along with mitochondrial DNA of Madeiran mice, suggests that Vikings also came to Madeira , prior to colonisation by Portugal.

There is a romantic tale about two lovers, Robert Machim and Anna d'Arfet in time of the King Edward III of England, 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 cointained in the Medici Atlas dated 1351, preserved at Florence, Italy, it would appear that Madeira had been discovered long before that date, possibly by Portuguese vessels under Genoese captains.

Portuguese discovery
In 1419 two captains of Prince Henry the Navigator, João Gonçalves Zarco and Tristão Vaz Teixeira, were driven by a storm to the island they called Porto Santo, or Holy Harbour, 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, together with captain Bartolomeu Perestrello.