Even within the legend theories there are variations, but one common thread is woven through out, that of the "Once Upon A Time" theme.
This legend, that is staged with familiar romantic overtones, in one form or another continues to play an intricate part in the history of this archipelago...
Ana's father has pledged her to a nobleman of much higher rank, though he is fully aware that Ana had fallen "madly" in love with Machin. Her father has the wedding date brought forward, and Machin is thrown into prison.
Machim somehow escapes and the young lovers flee and board a ship for France. Their voyage to France is met by a storm, that sends their ship drifting at sea. After fourteen days, and only by the Good Graces of God, they come ashore in a beautiful wooded bay on an uninhabited island.
The lovers accompained by members of the crew and loyal servants, spend three "happy" days on the island. When they decide to return to the ship, another storm appears and the ship is destroyed.
A frail and weary Ana despairs, and dies in the arms of her lover of a broken heart. Machin, grief-stricken, buries his beloved Ana and places wreaths of flowers on her grave. Within days Machin also dies.
Legend continues this version of the tale by noting that the remaining surviving members of the crew and servants bury Machin next to his beloved Ana. They then build a makeshift raft and attempt to sail back to England, only to crash on the Moroccan coast, where they are captured and imprisoned.
Their accounting of the events as told to fellow prisoners reach the ears of nobles in Portugal. It is these accounts that "ignite" Portugal's interest in future exploration of this region
It is further noted that the wooded island mentioned in this version is said to have been the Island of Madeira.
Further documentation records that the Castilians as early as 1342 had taken part in expeditions to the Canary Islands. All that would be needed to bring these expeditions into waters from which Madeira, Porto Santo or the Desertas might be seen would be a small deviation from the direct route which leads to the Canaries.
Still another source, a 1351 Genoese map, shows an island called "isola della Lolegname," translated as "Island of Wood."
These are but a few of the facts that some historians believe help displace the theory that two of Infante D. Henriques' (Henry the Navigator) squires actually discovered the islands of Madeira and Porto Santo, in 1418.
It is now believed by many that Prince Henry simply ordered his squires to settle these already known, but uninhabited islands.
Two of Prince Henry's veteran knights, Joao Goncalves Zargo and Tristao Vaz Teixeira, were sent in 1418, to explore the seas off Guinea.
Their ships ran into ferocious storms and were swept away to an island where they found shelter, and which they named Porto Santo. After exploring the island they established that it would be suitable for settlement.
Though, as they fixed their gaze on the distant horizon, they immediately became intrigued by the sight of a "large strange cloud" of what appeared to be smoke. Fearful that this might be the "end of the world" as they knew it then, they decided not to investigate.
At last the decision was made that they would return to Lisbon, and attempt to convince Prince Henry that they should be given the opportunity to settle this island, they called Porto Santo. For would it not be an ideal "stopping off" point for future Portuguese exploration of the region?
With their "formulated game plan" in hand they prepared to return to Lisbon. Half of the crew remained on the island, while the two squires and the remaining crew members set sail for Lisbon.
Upon arriving in Lisbon, their meeting with Prince Henry proved most favorable and with his approval, plans were made to return to Porto Santo.
On the return voyage in 1420, they were accompanied by another squire, an Italian named, Bartolomeu Perestrelo, who was interested in the economic possibilities of the new land.
As they approached Porto Santo they were once again, intrigued by the "strange cloud" that could be seen on the horizon. After coming ashore on Porto Santo, they could no longer refrain from investigating this strange sight. With a handful of crew members, Zargo and Teixeira set out to explore the source of this sighting.
As they grew near, they could see that it was not "smoke" but a fine mist that engulfed an entire island. An island densely populated with timber. Once they set foot on shore they named the island..." Ilha da Madeira"...Island of Wood.
When the news of Madeira reached Prince Henry, he entrusted the responsibility of populating the islands to his three squires. They were to share the same objectives, making these islands a prosperous Portuguese colony.
The three were granted governorships. The eastern portion of Madeira, with its "administrative center" (concelho) in Machico was given to Tristao Vaz Teixeira. Joao Goncalves Zargo was granted the western portion with its concelho in the city of Funchal. Finally the island of Porto Santo would be developed by Bartolomeu Perestrelo.
Going about accomplishing the colonization of Maderia and Porto Santo was by no means an easy task.