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

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) azulejo tiles from the 15th and 16th centuries. The ceiling of the Sala dos Brasões is painted with the coats of arms of 72 noble families, and the grand Sala dos Cisnes has a remarkable ceiling of painted swans.  Bilingual descriptions in each room let you enjoy them at your own pace.

This estate, 6 km (3½ 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 biggest draw in Sintra, this colorful palace is a glorious conglomeration of turrets and domes awash in bright 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 Wilhelm Ludwig von Eschwege, to build the palace 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 swans glide the mystical surrounds. Portugal's last monarchs used 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 palace walls, peek into turrets, and refresh at one of two on-site cafés. A path beyond an enormous statue (thought to be Fernando II himself, forever guarding the park and the palace) on a nearby crag leads to the Cruz Alta, a 16th-century stone cross 1,732 feet above sea level, with stupendous views.  Buy timed tickets in advance and arrive at least an hour before your designated tour time; you will either have to take a shuttle bus or make the 30-minute uphill trek to the palace from the park entrance.

A 10-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 favorite 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.

The battlemented ruins of this 10th-century castle still give a fine impression of the fortress that finally fell to Christian forces led by Dom Afonso Henriques in 1147. Panoramic views from the serrated walls explain why the Moors chose the site. It's visible from various points in Sintra itself, but for a closer look follow the steps that lead up to the ruins from the back of the town center (40 minutes going up, about half that coming down). No cars are allowed, but you can save your legs by catching Scotturb Bus 434 or taking a tuk tuk ride from town. The castle is walkable from the Palácio da Pena, since it's accessed from the same road and its entrance is somewhat below that of the Palace park.

The entrance to this extraordinarily austere convent, 13 km (8 miles) southwest of Sintra, sets the tone for the severity of the ascetic living conditions within. From 1560 until 1834, when it was abandoned, eight friars—never any more, never any less—prayed in the tiny chapel hewn out of the rock and inhabited the bare cells, which were lined with cork in attempt to maintain a modicum of warmth. Impure thoughts meant a spell in the Penitents' Cell, an excruciatingly dark space.

Barack Obama and the late Queen Elizabeth II have been among the famous faces peering from the windows of this modern museum dedicated to the workings of 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 19th-century palace was featured in Roman Polanski’s The Ninth Gate. It initially belonged to the Biester family and was kept as a private residence until 2022, when it opened to the public for the first time. Much of the decor has been kept in its original form, from the ornate wooden staircases to the painted ceilings with floral motifs. The highlight, however, is the large windows that look out into Sintra’s hills. Take a stroll around the surrounding gardens, and you’ll spot the town’s major sites rising in the distance.