The history of this magical place begins in the 12th century, when a chapel dedicated to Our Lady of Pena existed there. On this same site, King Manuel I ordered the construction of a monastery, the Royal Monastery of Our Lady of Pena, later given to the Order of Saint Jerome. The earthquake that struck Lisbon in 1755 left the monastery practically in ruins. Even in its dilapidated state, the Monastery maintained its activity, but almost a hundred years later, in 1834 when religious orders were abolished in Portugal, it was abandoned. The Pena Park still preserves corners that recall this period, such as the Monk's Grotto, a place where the monks practiced seclusion. Two years later, in 1836, Queen Maria II married Ferdinand of Saxe-Coburg and Gotha, a prince of the House of Saxe-Coburg and Gotha, nephew of the reigning Duke of Coburg, Ernest I, and King Leopold I of Belgium. According to the marriage contract, Ferdinand received the title of king consort.

Sintra was, in the 19th century, one of the first cradles of Romantic architecture in Europe. Its unique climate and resulting natural beauty attracted the attention of those who, moved by the landscape, dared to embellish it with dazzling architecture in Edenic harmony, conducive to the contemplation of the Beautiful and the Sublime. It is within this picturesque setting that we find, just outside the historic center of Sintra, Quinta da Regaleira. Conceived and built during the late 19th century, it reflects the sensitivity and cultural, philosophical, and scientific interests of its owner, António Augusto de Carvalho Monteiro (1848-1920), combined with the virtuosity of the Italian architect-set designer Luigi Manini (1848-1936). The culture and creativity of these two personalities resulted in an eclectic-revivalist architectural ensemble, with a particular focus on Manueline, Renaissance, Medieval, and Classical styles.