5 Best Sights in Sintra, Sintra, the Estoril Coast, and the Setúbal Peninsula

Barack Obama and Queen Elizabeth II have been among the famous faces peering from the windows of this modern museum dedicated to the workings of the mass media. Inside a handsome building with wrought-iron balconies, it combines interactive exhibits such as a giant touch-screen tablet highlighting world-changing events with thought-provoking examinations of how the media has covered various topics, including Portuguese soccer luminary Cristiano Ronaldo. The bright exhibits and interactive devices should keep younger visitors occupied for an hour or so.

This estate, 4 km (2½ miles) west of Sintra, was laid out by English gardeners in the mid-19th century at the behest of a wealthy Englishman, Sir Francis Cook. The centerpiece is the Romantic-style, three-dome Palácio de Monserrate, which combines Gothic and Indian architectural influences with Moorish touches. The gardens, with their trickling streams and waterfalls, are famed for an array of tree and plant species, with notable species clearly marked and identified. 

The enormous twin chimneys rising out of Sintra Palace are among the town's most iconic landmarks. There has probably been a palace here since Moorish times, although the current structure dates from the late 14th century. It is the only surviving royal palace in Portugal from the Middle Ages and displays a combination of Moorish, Gothic, and Manueline architecture. The chapel has Mudéjar (Moorish-influenced) azulejos from the 15th and 16th centuries. The ceiling of the Sala das Armas is painted with the coats of arms of 72 noble families, and the grand Sala dos Cisnes has a remarkable ceiling of painted swans. The Sala das Pegas (magpies) figures in a well-known tale about Dom João I (1385–1433) and his dalliance with a lady-in-waiting. The king had the room painted with as many magpies as there were chattering court ladies, thus satirizing the gossips as loose-tongued birds. Bilingual descriptions in each room let you enjoy them at your own pace.

The biggest draw in Sintra, this Disney-like castle is a glorious conglomeration of turrets and domes awash in pastels. In 1503 the Monastery of Nossa Senhora da Pena was constructed here, but it was badly damaged by the devastating earthquake that struck Lisbon in 1755. The monastery remained active in the ruined building, but it was abandoned when religious orders were expelled from Portugal in 1834. In 1836, the ruins were purchased by Maria II's consort, Ferdinand of Saxe-Coburg and Gotha. Inspired by the Bavarian castles of his homeland, Ferdinand commissioned a German mineralist and mining engineer, Baron Eschwege, to build the castle of his fantasies, in styles that range from Arabian to Portuguese Gothic. Work was finished around 1860, by which time he was Fernando II. The surrounding park is filled with trees and flowers, as well as hidden temples, grottoes, and the Valley of the Lakes, where black swans sit regally. Portugal's last monarchs used the Pena Palace as a summer home, the last of whom—Queen Amélia—went into exile in England after the Republic was proclaimed on October 5, 1910. Inside is an ostentatious and often bizarre collection of European furniture, ornaments, and paintings. Placards explain each room. Visitors can walk along high castle walls, peek into turrets, and finally reward themselves with a drink and a snack at one of two on-site cafés. A path beyond an enormous statue (thought to be Ferdinand II himself, forever guarding the park and the palace) on a nearby crag leads to the Cruz Alta, a 16th-century stone cross 1,782 feet above sea level, with stupendous views.

A five-minute walk along the main road past the tourist office takes you to one of Sintra's most intriguing privately owned mansions. Quinta da Regaleira was built in the early 20th century for a Brazilian mining magnate with a keen interest in Freemasonry and the Knights Templar (who made their 11th-century headquarters on this site). The estate includes gardens where almost everything—statues, water features, grottoes, lookout towers—is linked to one or the other of his pet subjects. Spookiest of all is the 100-foot-deep Poço do Iniciático (Initiation Well)—an inverted underground "tower." Audio guides in English are available at reception.