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

The most visited attraction in the area around Cascais is the forbiddingly named Mouth of Hell, one of several natural grottoes in the rugged coastline. Located just 2 km (1.2 miles) west of town, it is best appreciated at high tide or in stormy weather, when the waves crash high onto the surrounding cliffs. You can walk along the fenced paths to the viewing platforms above the grotto and peer into the abyss. A path leads down to secluded spots on the rocks below, where fishermen cast their lines. The bleakly beautiful spot is where English occultist and magician Aleister Crowley faked his own suicide in 1930, shocking onlookers when he appeared at a Berlin art gallery three weeks later. A white plaque at the site marks the intriguing occasion, together with the text of the "suicide note" he left behind.

This salt-encrusted headland—crowned by a whitewashed convent surrounded by 18th-century pilgrim rest houses—is the southwestern point of the Setúbal Peninsula, marked by a red-and-white lighthouse. It's a ruggedly beautiful spot, where the cliffs rise hundreds of feet out of the stormy Atlantic. To the north, unsullied beaches extend as far as Caparica, with only local roads and footpaths connecting them. It's a good spot for hiking, with marked trails leading down to some clearly visible dinosaur footprints.

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.

Occupying the entire southern coast of the Setúbal Peninsula is the Parque Natural da Arrábida, dominated by the Serra da Arrábida—a 5,000-foot-high mountain range whose wild crags fall steeply to the sea. There's profuse plant life at these heights, particularly in spring, when the rocks are carpeted with colorful wildflowers. The park is distinguished by a rich geological heritage and numerous species of butterflies, birds, and mammals (you might spot foxes and mongoose, and even wild boar). The park is a favorite destination for bikers, hikers, horseback riders, and adventure-sports enthusiasts. There are also some lovely hidden beaches for those prepared to put in the footwork.

This small fishing village is a popular destination for Lisboetas, who appreciate the beautiful beaches, whose wonderfully clear blue-green waters and white sands create a dramatic contrast with the green, pine-covered hills. A handful of good fish and seafood restaurants offer terraces with views out to sea. Due to the high number of visitors, cars are banned mid-June to mid-September, but free buses run here from Setúbal to Portinho da Arrábida and other picturesque beaches. Parking can be difficult even outside peak season.

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.

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.

This 15th-century Church of Jesus, perhaps Portugal's earliest example of Manueline architecture, was built with local marble and later tiled with simple but affecting 17th-century azulejos. The architect was Diogo de Boitaca, whose work here predates his contribution to Lisbon's Mosteiro dos Jerónimos (Jerónimos Monastery). Six extraordinary twisted pillars support the vault; climb the narrow stairs to the balcony for a closer look at the details, which would soon become the very hallmark of Manueline style. Outside, you can still admire the original, although badly worn, main doorway and deplore the addition of a concrete expanse that makes the church square look like a roller-skating rink. The church's original monastic buildings and Gothic cloister—on Rua Balneário Paula Borba—house the Museu de Setúbal, a museum with a fascinating collection of 15th- and 16th-century Portuguese paintings, several by the so-called Master of Setúbal. Other attractions include azulejos, local archaeological finds, and a coin collection.

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. 

A favorite destination for runners, hikers, cyclists, and triathletes, Sintra-Cascais Natural Park is renowned for its well-marked trails across the forest-covered slopes of the Serra da Sintra. It's also known for its wild beaches, towering sand dunes, and its abundant flora and fauna The bleakly beautiful Cabo da Roca and its lighthouse mark the continent's westernmost point and are the main reason that non-athletes make the journey to Sintra-Cascais Natural Park. The cliffs tumble to a frothing sea below, and on the cape a simple cross bears an inscription by Portuguese national poet Luís de Camões.