14 Best Sights in Sintra, the Estoril Coast, and the Setúbal Peninsula, Portugal

Sitting high above the city is the Castelo de Sesimbra, which was conquered in 1165 by Dom Afonso Henriques but fell back into the hands of the Moors until 1200. The castle lost importance and fell into disrepair during the next several hundred years until Dom João IV ordered that it be adapted for the use of artillery in 1648. Classified as a National Monument, reconstruction was done to restore it to its previous glory after the great earthquake of 1755. From Sesimbra, a steep marked walking trail leads up the side of the pine-covered hill to the castle grounds. Aside from the incredible views of the ocean and the city below, there is a chapel, a small museum, and a café with an outdoor patio where you can enjoy a gin and tonic or a bagaço (a clear Portuguese liquor) as the sun goes down.

For an understanding of the maritime history of Cascais, head to this modern museum. Here, the town's role as a fishing village is traced through model boats and fishing gear, period clothing, old photographs, and exhibits of curious sea creatures.

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. 

Built in a similar style to the celebrated palace at Versailles and now restored from pink to its original blue, Queluz National Palace was ordered as a royal summer residence by Dom Pedro III in 1747. Architect Mateus Vicente de Oliveira took five years to make the place habitable; Frenchman Jean-Baptiste Robillon spent 40 more executing a detailed baroque plan that also comprised imported trees and statues, and azulejo-lined canals and fountains. You can tour the apartments and elegant staterooms, including the frescoed Music Salon, the Hall of Ambassadors, and the mirrored Throne Room with its crystal chandeliers and gilt trim. 

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.

Still under the radar even among Lisboetas, Cova do Vapor is a fishing hamlet perched at the point where the river Tagus meets the Atlantic Ocean. The soft-sand beach is Caparica's closest point to Lisbon, and there are glorious views over the city's domes and towers, but its rustic beach shacks and hand-constructed wooden playground make Cova do Vapor Beach feel like another world. While crowds of surfers pack most of the Costa da Caparica, there are still vast swaths of space on the sands and gentle dunes here. Amenities: food and drink; parking (no fee). Best for: solitude; swimming; walking.

Wine-loving locals flock to this scenic family estate to stock up on its wonderful red and white table wines. It’s hidden down a long dusty track, but well worth the trip: you can take a seat at one of the outdoor tables and enjoy those excellent wines by the bottle or glass, along with the Quinta’s equally delicious homemade cheeses and preserves. Friendly goats, piglets, and ponies keep younger visitors entertained while the adults enjoy the food, wine, and beautiful views of the surrounding vineyards and the Arrábida hills.

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.

When young Lisboetas want to go to the beach, they'll often head to the Costa da Caparica, which is packed in summer and exudes a more youthful vibe than Cascais and Estoril. Formerly a fishing village, the town itself is rather lacking in charm these days, but the beachfront is lively with cafés and bars catering to a relaxed, surf-loving clientele. Avoid the crowds by heading south toward the less accessible dunes and coves at the end of the peninsula. Each beach is different: the areas nearest Caparica are family-oriented, whereas the more southerly ones tend to attract a younger crowd (there are some nudist beaches, too). Amenities: food and drink; lifeguards; parking (fee); showers; toilets; water sports. Best for: partiers; sunset; swimming; walking.

Vila Nogueira de Azeitão's agricultural traditions are trumpeted on the first Sunday of every month, when a country market is held near the center of town. Apart from the locally produced wine, you can buy several kinds of local cheeses with an amanteigado (butterlike) texture.

Visitors to this grand mansion dating back more than a century can get a peek into how local aristocracy once lived while admiring an impressive display of 18th- and 19th-century paintings, ceramics, and furnishings. The canary-yellow building makes a dramatic backdrop to the small beach next door, which is open to the public and attracts groups of swimmers and sunbathers on hot days.

Take respite from the crowds at this relaxing park next to the palacial Museu dos Condes. There's a tree-shaded spots for picnickers plus a large lawn for sunbathers (expect strolling ducks and peacocks for company). There's also a playground and a pleasant café.