What happens when an eccentric, wealthy, Romantic-era mystic with interests in Templar and Masonic symbolism hires a set designer to create his dream castle? In the case of António Augusto Carvalho Monteiro and his Italian architect, Luigi Manini, you get the wild estate of Quinta da Regaleira in Sintra.

That’s the five-story palace, and in many ways, it’s the most normal element on site. Because things get a lot stranger from here, starting with the most famous feature on the property: the Initiation Well.

Into the Depths

To be clear, this is not really a well at all — it’s nine levels of fifteen steps each, winding down in what may be a reference to the Divine Comedy’s descent into hell.

Monteiro was fascinated with symbols and secrets. As best we know, he ran a secret organization, perhaps related to the Knights Templar. If the rumors are true, new initiates would walk down these stairs on the night of their induction, blindfolded and carrying swords next to their hearts. Once they made it to the cross at the bottom, they’d end up in a creepy network of tunnels and caves.

Fortunately, the tunnels are now nicely paved and lit. But back in the day, initiates would have had to stumble through a damp labyrinth in the dark.

It wasn’t just these initiates who faced this kind of darkness — the whole Quinta da Regaleira property is a warren of caves and grottos.

Some of the tunnels lead to lakes, some run into stairs that go to other levels of the property, and some simply dead end. All of the tunnels are covered in stones brought in from an area by the sea, to give the illusion of being in a very different underground world. And if you’re feeling brave, you can still wander through these wet, pitch-black grottos.

If the legends are true, once the initiates braved the darkness, they emerged at a waterfall lake — which they would then cross using a series of stepping stones (you can probably imagine the symbolism related to walking on water) …

… before walking downhill to the Quinta da Regaleira chapel.

Into the Light

The chapel was deeply steeped in symbolism, both outside and indoors. As you can see, the floor mosaics in the chapel highlight the Cross of the Order of Christ, a Templar cross successor.

Manini designed the property with a bevy of to take visitors up into the light.

Indeed, Quinta da Regaleira has a higher tower-to-acre ratio than most places I’ve seen.

If you want to continue the ascending and descending metaphor, there are stairs in all sorts of places.

So Many Symbols

What other symbols might you find here? Well, there are ibises (which are connected to the human soul and the afterlife) …

… the Eye of Providence …

… lions (traditional Knights Templar symbols of power and courage) …

… dragons (guardian beings) …

… and Christian iconography galore.

Of course, while we know for certain what some of these symbols mean (Noah’s Ark is pretty clear), we can’t be sure about most of this. There’s a lot of dicey speculation out there about symbology. And the fact is that neither the owner nor the architect of Quinta da Regaleira left information about why they included various elements of the palace or the park. It could be symbolism, but some of it may just have been whimsy.

Curious Creatures

After all, there’s a lot more out there, from dogs …

… to frogs …

… to whatever these things might be.

In any case, Quinta da Regaleira is well worth a visit. You’ll be surrounded by dozens (maybe hundreds) of other tourists — this is one of the most popular palaces in Sintra — but it’s an incredible and unusual place.

Inspiration Beyond the Quinta da Regaleira in Sintra

• Planning a bigger trip? Compare all of Sintra’s palaces in my complete guide to help choose the best ones for your visit.
• For more palaces, explore Monserrate Palace, one of Sintra’s most romantic estates — or dive into the history of the National Palace of Sintra, right in the heart of town.
• Starting from Lisbon? Don’t miss my guide to 14 fun things to do in Portugal’s capital.