The mountain-top town of Sintra is effectively a 19th-century fever dream brought to life — a misty, candy-colored playground where Romanticist architecture meets dense, prehistoric-looking forests. I thought the inside and outside of the castle were mad-hatter surreal, and the guidebooks aren’t wrong when they say that Sintra is a must-see if you are in Lisbon… or Portugal…or the planet Earth.
Known to the Romans as the “Mountains of the Moon” due to its ethereal fog, this town served as the ultimate summer retreat for royalty looking to escape Lisbon’s heat. Sintra has its own weather. It can be 80° in Lisbon and a foggy, 60°F horror-movie set in Sintra at the same time.
Today, it’s a vibe-heavy mix of occult-themed estates and lush “secret” gardens that feels more like a movie set than a real town. In fact, “The Ninth Gate”, a 1999 neo-noir supernatural thriller directed by Roman Polanski and starring Johnny Depp, was filmed in Sintra. Based on Arturo Pérez-Reverte’s novel The Club Dumas, the film follows a cynical rare-book dealer who becomes entangled in a satanic conspiracy.
Sintra is essentially the world’s most successful mood board come to life. Long before it became a UNESCO World Heritage Site, it was a misty mountain retreat where Portuguese royalty and eccentric millionaires built their wildest architectural what-if dreams.
The “Royal Playground” Phase took place between the 12th and 18th centuries, beginning with King Afonso Henriques’s expulsion of the Moors in 1147. He liked their hilltop castle so much that he kept the over-the-top vibe. For centuries, Sintra was the ultimate summer mountain escape for royals hiding from Lisbon’s heat, an amusement park for the idle rich, like a psychedelic Monaco in the mountains.
The massive white-and-black palace is famous for its two 33-meter conical chimneys, which visitors often joke look like a medieval nuclear power plant. You should book your ticket online in advance for about $15, as they often sell out. The self-guided tour takes about an hour and is very popular. We especially liked the medieval kitchens and the rooms that were decorated with intricate Mudéjar tilework.
In the National Palace of Sintra, the king built the Gossip Room called the Sala das Pegas (Magpie Room). Legend says King John I was caught flirting with a lady-in-waiting, and when the court started gossiping, he had the ceiling painted with 136 magpies—one for each gossiping lady—each holding a banner that says Por Bem (“For Good”) to shut them up.
Next came the Romantic Fever Dream Phase in the 19th Century. In the 1800s, King Ferdinand II (the “Artist King”) decided a ruined monastery wasn’t cool enough. So he built the Pena Palace, a Crayola-colored fortress overlooking the city that looks like Disney World on acid. Ferdinand didn’t pick a specific architectural style; he picked all of them—Gothic, Moorish, Renaissance, and Manueline. It definitely reminded me of the trippy, dripping Gaudí buildings in Barcelona.
Over the front door of the Pena Palace drips the Triton, a menacing half-man, half-fish stone creature guarding the gate, just to make sure things begin gloriously weird and set the crazy tone for the rest of your visit.
Then came the Occult & Emo Phase (Late 19th – Early 20th Century). Brazilian coffee kingpin Antonio Augusto Carvalho Monteiro, also known as “Monteiro the Millionaire”, built Quinta da Regaleira, an estate for someone who thinks standard gardens are boring. Monteiro collaborated with the brilliant Italian architect and opera set designer Luigi Manini to turn his 10-acre estate into an interactive, stone-carved textbook of esoteric knowledge. The landscape is dense with symbols pulling from Freemasonry, alchemy, Rosicrucianism, and the Knights Templar.
The cornerstone of the garden is the Inverted Tower, better known as the Initiation Well, a 27-meter hole in the ground with a spiral staircase designed for secret Freemason or Templar-style rituals. You descend into “hell” (the bottom) and walk through dark tunnels to “rebirth” into the light of the gardens. The entire place is basically a playground for goths and mystics, filled with hidden grottoes, tunnels, secret passages, and Masonic symbols.
Sintra is literally overrun with wide-eyed tourons every day. It’s industrial-strength tourism. The castle tour is an orderly, slow-moving, keep-your-mouth-shut-when-inside cattle drive. But the Pena Castle is worth all the minor annoyances. And it helps that they have a steep, 15-minute walk up the driveway or through the forest trails to get there. That weeds out the slow and the lame, though you can pay to ride a shuttle if you are unable to walk up the hill, but they only run intermittently.
We arrived in Sintra around 9, as the palace was just opening, and long lines were already forming. The palace tour lasted about an hour. If you go, get there as early as you can, because by 10 the place is overrun and you will end up waiting and waiting to get in. The tour is fun and interesting, but they keep you moving because they have so many people to get through the place. I stopped right at the start, in the dining room, to examine the ornate blue-and-green table, and was immediately told to giddyup-go.
Three million people visit Sintra each year. That comes out to 8,000 people a day crammed into a pretty small area. So, be prepared. Here’s what you need to know when you are planning your visit.
Advance Booking is Mandatory: You need to purchase timed-entry tickets for many of the attractions well in advance. Do not try to buy them on the day of your visit, or you risk waiting up to 3 hours or selling out.
The Microclimate: Because of its high elevation, Sintra is consistently about 5–9°F cooler than Lisbon. It is prone to heavy fog, even when the rest of Portugal is sunny.
Transportation & Driving: Do not rent a car to drive up Sintra’s narrow, winding hills. Parking is incredibly scarce, and many historic streets restrict private vehicle access. Instead, take the train from Lisbon and use the local tourist buses (such as the 434 and 435) to navigate the attractions.
Don’t try to wing it on your own. Take a tour!
The Medieval town of Sintra is also ten pounds in a five-pound sack. It sits below the castle like a mini-maze of stone shops and houses, and there is a relentless crush of people looking for Chinese-made Portuguese souvenirs. I can’t imagine living there. In fact, I’m sure they hate the tourons. We asked a police officer for directions, and he intentionally sent us in the wrong direction while never looking up as he played with his phone.
That said, the town has some interesting attractions worth noting.
The Cantinho Lord Byron (also known as the Lord Byron Café) is Sintra’s primary gathering spot dedicated to the celebrated English poet. This establishment functions as a cozy tavern and wine bar where fans and visitors celebrate Byron’s legacy and his description of Sintra as a “glorious Eden”.
During World War II, neutral Sintra was a hive for international spies. British agents who operated discreetly from the Penha Longa Resort tried to intercept German codes while tourists snapped photos nearby. Netflix is probably working on a clever series about the place right now.
The Convento dos Capuchos, or “Cork Convent”, is a 16th-century monastery where monks lived in tiny cells lined with cork for insulation — a medieval version of eco-friendly smart housing.
The Alto do Chá (Tea Hill) viewpoint wasn’t just named for its views; it was the site of Portugal’s first experimental tea plantation in 1883. Driven by King Ferdinand II’s romantic and cosmopolitan vision to transform the mountain landscape into an exotic oriental retreat. To evoke a far-eastern atmosphere, the area was designed using 13th- and 14th-century Cantonese illustrations as inspiration. It featured a winding network of paths that climbed granite cliffs, decorative ponds, cascades, and an original water-and-irrigation system. Growing at roughly 1,500 feet above sea level, the tea plants thrived in the cracks of rocky outcrops, benefiting from Sintra’s misty, humid mountain climate.
Everyone has heard about the Initiation Well at Quinta da Regaleira, but there is actually a second, less famous “Unfinished Well” (Poço Imperfeito) on the same grounds that is connected to a hidden, subterranean network of rock-lined tunnels that snake beneath the estate’s gardens. The straight staircase of the Unfinished Well never reaches the surface, symbolizing earthly imperfection. And trying to navigate either of the wells in the dark at night, which is how the rituals were carried out, would have been terrifying.
We spent a few hours roaming aimlessly around Sintra after the trip around the magic palace. We ate a lousy lunch on the grand patio of the Café Paris, located in the city square and offering outstanding people-watching, and then we did the obligatory pilgrimage to Casa Piriquita for a Travesseiro (“Pillow”) pastry. The original bakery has been using the same secret recipe since 1862. So while the United States was tearing itself to shreds in a bloody Civil War, the people of Sintra were concocting pastries. How’s that for a little perspective?
By two, we were back in the heavenly tour van and heading through Sintra-Cascais Natural Park on the Portuguese Riviera, one of the 13 Natural Parks of Portugal. Although it was designated a Natural Park by the Portuguese Government only in 1994, it has been protected since 1981. The park includes the Serra de Sintra Mountain Range and extends to the coast and Cabo da Roca, continental Europe’s westernmost point. The rocky headland was enshrouded in a thick fog at three in the afternoon, and when we stood at the monument, the land was bathed in sun, but the ocean was nowhere to be seen, even though we could hear it crashing against the rocks right below.
We were only an hour west of Lisbon, but it seemed a world away.
And that, my friends, is how Portugal rolls. It challenges the senses and always keeps you coming back for more.
