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Sintra, Portugal

The Pena Palace in São Pedro de Penaferrim, Sintra, Portugal

Sintra is like something out of a fairy tale. A town set among the pine trees on the edge of the lush Sintra-Cascais Natural Park, Sintra was the summertime escape of European royalty and nobility and today is replete with beautiful gardens, castles and palaces to explore. The town and its hills are a UNESCO World Heritage Site, the Cultural Landscape of Sintra, and the centre, Sintra-Vila, is easily accessible from Lisbon, just a forty-minute train ride away. The English author Robert Southey referred to Sintra as ‘the most blessed spot on the whole inhabitable globe.’ On Day 3 of our Discover Portugal small group tour, we spend a full day in Sintra and on the nearby coast.

Small Group Tour

Discover Portugal

18-Day Tour · Lisbon to Porto · Small group, up to 16 travellers, solo travellers welcome

Day 3 is a full day out of Lisbon: Pena Palace early, before the crowds, travesseiros in Sintra town and Quinta da Regaleira, then Cape Roca and the coast road to Cascais.

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History of Sintra

Sintra-Vila, the heart of Sintra

During the Roman occupation of the Iberian peninsula, the people of the Sintra area were enrolled in the Galeria, one of the voting tribes of Roman citizens, and Roman remains in the town today show a Roman presence in the area lasting into the 5th century AD. Roman occupation was followed by Moorish rule, and Sintra changed hands more than once in the wars of the Reconquista. After the conquest of Lisbon in October 1147, King Afonso I, supported by the crusaders, took Sintra for good, with both the hilltop Castle of the Moors and the Moorish palace in the town below (now the National Palace of Sintra). Sintra was integrated into Christian dominions along with Almada and Palmela after their surrender. King Afonso I established the Church of São Pedro de Canaferrim within the walls of the Moorish Castle to mark his success. In the centuries that followed, Sintra became the playground of the Portuguese monarchy, who built palaces and houses in the forests.

The proclamation of a Portuguese Republic in 1910 transformed the bohemian atmosphere of Sintra. Economic development was promoted and different industries began to grow, particularly with the urbanisation of the town once a rail link to Lisbon was built. Summer travellers began to make their way to Sintra and this resulted in the building of many Portuguese summer residences. These projects benefited the town, increasing tourism and attracting notable and wealthy Portuguese residents.

Today, Sintra is one of Portugal’s most expensive and sought after real estate markets, known for its historic villas, luxury estates and impressive culinary scene. It is often named among the most desirable places to live in Portugal.

Sights to See

National Palace of Sintra

The Palacio Nacional de Sintra is the best preserved medieval royal palace in Portugal, with its structure remaining more or less unchanged since the 16th century. It has also been inhabited almost continuously since at least the early 15th century up until the late 19th century. The royal palace is the star of Sintra-Vila, the centre of Sintra, and instantly recognisable from the iconic twin conical chimneys that dominate the skyline.

The National Palace of Sintra – you can see the two conical chimneys from the kitchen

Originally, the site of the palace was a Moorish castle and the residence of the Islamic Moorish Taifa of Lisbon rulers of the region. In 1147, the village was conquered by King Afonso I, who took the castle for his own use. However, the first king to start updating and renovating the palace was King Dinis I (reigned 1279–1325). Today, the main surviving feature from his changes is the Royal Chapel. The chapel’s tiled floors and geometrically patterned wooden ceiling are some of the oldest examples of Moorish craftsmanship in Portugal (Dinis commissioned Moors living in the neighbouring village to help with the chapel).

The palace that we see today is mostly the work of King João I in the 15th century and King Manuel I in the early 16th century. King Joao I added a kitchen and the conical chimneys, the elegant Swan Room (with swans painted on the ceiling) and beautiful patios embellished with geometric azulejo tiles. King Manuel I added a whole wing to the palace (Manuel’s Wing) and the Coats of Arms Room.

The site was chosen to be a royal palace because of its proximity to Lisbon, the agricultural quality of the area, and the well-stocked hunting grounds. As a result, this is the place which Portuguese royals would have called home for more of their history than anywhere else. In the 19th century in particular, the Palace of Sintra was frequently inhabited. In 1910 it was classified as a National Monument, and it was restored from the late 1930s. Since then, it has become an important historical attraction.

Quinta da Regaleira

Quinta da Regaleira, a spectacular 20th century estate

One of the delights of Sintra is the enchanting 20th century estate, Quinta da Regaleira. Incredibly ornate and eccentric, the decorative residence exists thanks to António Augusto Carvalho Monteiro, a Brazilian-born collector and naturalist. Carvalho Monteiro amassed a great fortune in Brazil and bought Quinta da Regaleira, then an elegant summer retreat with a majestic house and chapel, from the family of the Baroness of Regaleira in 1892. Inspired by the nearby Pena Palace and the Neo-Manueline style of Buçaco Palace in Mealhada, Carvalho Monteiro hired Luigi Manini (who designed Buçaco Palace) to transform the Quinta da Regaleira. Manini’s project was completed in 1910 and the result was a design full of mysticism and theatre: a magical palace surrounded by gardens full of secret passageways and underground grottoes. It is said that hidden throughout the estate are symbols related to alchemy, Masonry, the Knights Templar, and the Rosicrucians.

Looking down the Initiation Well at Quinta da Regaleira

One of the most unusual attractions at Quinta da Regaleira is the Initiation Well, a subterranean tower sinking 27 metres into the earth accessible by a monumental spiral staircase. The well has never held water; it is thought to have been built for symbolic, perhaps initiatory, use, and the stairs lead you all the way to the bottom. From there, tunnels lead off through the rock. At the time of writing the visitor route runs one way, from the well to the Eastern Grotto, and the Waterfall Path is closed, so follow the estate’s signed route on the day. It is an extraordinary experience and one of the most amazing and curious aspects of the Quinta da Regaleira. Our guide to Quinta da Regaleira covers the gardens, the symbolism, timed tickets and how many steps are involved.

The Castle of the Moors

The Moorish Castle presiding over Sintra

The Castle of the Moors

The Castle of the Moors sits at an altitude of 412 metres atop a wooded hill, and with its iconic ramparts stretching down the mountain ridges, it is a striking sight. Built around the 10th century by the North African Moors during their conquest of the Iberian Peninsula, the castle was taken by Christian forces after the fall of Lisbon in 1147. Archaeological excavations at the site have uncovered the remains of a Moorish quarter, lived in from the 10th to the 12th century. Once Afonso I had taken the castle, the small Church of São Pedro de Canaferrim was built inside its walls, and while the monarchs of Portugal continuously used the castle, it was not as important as it had been during the Moorish rule.

The castle was restored in the 19th century by King Ferdinand II and in 1954 a few of the cliffs were cleared to establish a picnic area near the castle, with the hopes of encouraging tourism. Much of what remains of the Castle of the Moors is the fortified stone walls which visitors can walk along. These are connected to lookout towers that provide incredible views of Sintra and the surrounding forests.

Pena Palace

Sitting atop a verdant hill in São Pedro de Penaferrim, Sintra, the Pena National Palace is a Romanticist castle and part of the UNESCO-listed Cultural Landscape of Sintra. In 1838, King Ferdinand II (Ferdinand of Saxe-Coburg and Gotha), the husband of Queen Maria II, bought the ruined monastery on the summit and set about building a summer palace for the Portuguese royal family, with the work supervised by the German mineralogist and engineer Baron Wilhelm Ludwig von Eschwege.

Ferdinand was known for having opulent tastes and he wanted a magnificent castle built that featured all kinds of architectural styles, meaning the result was a palace that was simultaneously Neo-Gothic, Neo-Manueline, Neo-Islamic and Neo-Renaissance. It is said to have been inspired by Stolzenfels and Rheinstein castles and Potsdam’s Babelsberg Palace. Today, it is considered to be one of the grandest examples of 19th-century Romanticism.

In 1910, the royal family left Portugal after the revolution, and the palace was classified that same year as a National Monument. It was later opened to visitors, and the palace and its grounds have since been restored. The stunning Pena Park surrounds the palace and spreads out over some 85 hectares (about 210 acres). Labyrinthic in style, the park is filled with walking routes, secret paths, pavilions, lakes, ponds and exotic trees. Among its sights are the Valley of the Lakes, the Chalet and Garden of the Countess of Edla and the Pena Farm. One of the most romantic ways to explore the park is by horse-drawn carriage; at the time of writing, Parques de Sintra runs short carriage rides past the lakes, fountains and old trees, booked online, so check the current route and times before you go. For timed tickets, walking routes and what to see inside, see our visitor’s guide to Pena Palace.

The Ducks’ Residence in Pena Park

Sintra makes for a great day trip from Lisbon but there are countless sites and monuments to see if you have more than a day. As well as the historic centre, there is the national park and Sintra mountains and the coast (Praia da Adraga) is just a 20-minute drive from town. About half an hour’s drive to the north is the vast palace-convent of Mafra. We also stop in Sintra on our Spain and Portugal tour.

Seeing Sintra on our Discover Portugal tour

On our Discover Portugal tour, Sintra is Day 3, a full-day trip from Lisbon. We set out early to explore the colourful Pena Palace before the crowds build, then transfer down to Sintra town to try the travesseiros (puff pastry filled with almond cream) from the Piriquita bakery. Still in Sintra, we visit Quinta da Regaleira, with its palace, chapel, grottoes and tunnels. The day continues to Cape Roca, the westernmost point of mainland Europe, and along the coast road to Cascais for free time before returning to Lisbon. The tour is rated Level 2, Moderate, and an Odyssey Program Leader travels with the group throughout. For the rest of the route, see our Portugal travel guide.