Celts have roamed this terrain, having left momentos of cromlechs and menhirs at various sites aroundthe city. The Romans called this area “The Mountain of the Moon.” Then in the 8th to 9th century, Muslims built a castle here. During Medieval times, the Portuguese royal family, overflowing with the pomp and riches from their colonial triumphs abroad, first came here to escape the heat (and stench) of the summer in Lisbon.  Beginning in the 14th century, the Portuguese aristocrats followed the royals to escape the crowds in the neighboring Lisbon beaches. Here they built impressive estates, called “quintas” (the name is derived since by law, a fifth of the land belonged to the king of Portugal.) Other signs of this aristocratic past remain: in the center of the Dr Gregorio d’Almeida square, there is a pillory which was used in the 16th century to tie up criminals.  Once  tied, the criminals would be  pelted by the population, either with vegetables or  fruits or depending on the severity of the crime, stones.

In the 184os, Ferdinand de Saxe-Coburg-Gotha, the Germanic  husband of Queen Maria the II, built an immense, almost farcical castle, combining all the luxurious elements of previous ornate and gothic masterpieces.

Sintra retained its reputation as a luxury beach escape until the 20th century. However, after the murder of the King and his heir in 1908 and the fall of the royal family shortly after, Sintra’s reputation and history was largely forgotten or at least laid to sleep for a while.