Castles in the Sky: Your Fairytale Guide to Portugal!

Castle, castle, fortress, castle. Swoon! Hopping from castle to castle is enough to get any traveler excited. Throw in mind-blowing medieval villages bolstered by staggering cliffs wrapped up by spectacular, sweeping views in every direction and I👏🏻am👏🏻 all👏🏻in👏🏻!
Spectacular, sweeping views from National Palace of Peña in Sintra, Portugal.
Scattered across lush grasslands, jaw-dropping seascapes and dramatic limestone outcrops, Portuguese castles comprise a small but important part of the historical heritage of the country. Did you know that there are more than 150 castles in Portugal? Well, there are. And to visit even a handful of them takes a bit of planning. By now, you might be asking yourself, “Which ones are ‘worth’ it?”
Parking is notoriously difficult and impossible to reach by bus. If you are planning a visit from Lisbon, it’s best to arrange private transportation.
The answer to this question, of course, is that it depends. How much time are you spending in Portugal? Are you traveling by car, bus or train? For purposes of this post, let’s assume you are traveling by train and simply want to maximize your time on the ground to include some of these fantastical structures in your itinerary. As with any of my posts, the ultimate purpose is to inspire your travels. Accordingly, following are my five favorite fairytale fortifications in Portugal!
Captivatingly colorful in appearance, this magical hilltop castle sits imposingly atop the highest hill above Sintra.
1. National Palace of Peña, Sintra, Portugal. Crowning the hills of Sintra is the National Palace of Peña. Captivatingly colorful in appearance, this magical hilltop castle sits imposingly atop the highest hill above Sintra. Its shape and structure are the very definition of fairytale architecture. Although the story of the palace dates back to the Middle Ages, its current appearance is owed to a relatively modern monarch.
Crowning the hills of Sintra is the National Palace of Peña.
During the 19th century, Portugal had a very romantic prince, the German-born Prince Ferdinand. A contemporary of Bavaria’s ‘Mad’ King Ludwig, the flamboyant Ferdinand hired a German architect to construct the fantasy palace of his dreams. What Ferdinand ended up with is this crazy, colorful casserole of Gothic towers, Moorish minarets and Renaissance domes. Gazing at this architectural masterpiece, it’s impossible not to feel all the Mad King vibes.

Gazing at this architectural masterpiece, it’s impossible not to feel all the Mad King vibes.

But, as with any fairytale, a word of warning: Peña is a bit hard to reach and a visit will require some deft planning. Parking is notoriously difficult and impossible to reach by bus. If you are planning a visit from Lisbon, it’s best to arrange private transportation.

Constructed during the height of the Portuguese Renaissance by order of King Manuel I, Belem Tower served to both welcome visitors and to protect Lisbon’s harbor.

2. Belem Tower. Located about five miles west of downtown Lisbon is the Belem District, a resplendent pincushion of important sights from Portugal’s Golden Age. Constructed during the height of the Portuguese Renaissance by order of King Manuel I, Belem Tower served to both welcome visitors and to protect Lisbon’s harbor. Today, it symbolizes the voyages that brought Lisbon to power. Perhaps the purest Manueline building in Portugal, this enchanting white tower is adorned with the symbols of King Manuel I’s reign, including the cross of the Order of Christ. Resembling a petite fairytale castle, Belem Tower is a must-see sight for any visitor to Lisbon.

Chock full of symbols linked to masonry, alchemy and tarot mysticism, this enchanting estate was constructed by a very wealthy and equally eccentric Free Mason.  

3. Quinta da Regaleira. Sintra is jam-packed with extravagant 19th century villas, but none are more intriguing than Quinta da Regaleira. Chock full of symbols linked to masonry, alchemy and tarot mysticism, this enchanting estate was constructed by a very wealthy and equally eccentric Free Mason. Perhaps the most bewildering of all the structures on the estate is the Initiation Well.

A destination unto itself, the Initiation Well is possibly the most famous attraction in all of Sintra and the subject of endless speculation and fascination for those interested in the Knights Templar.

A destination unto itself, the Initiation Well is possibly the most famous attraction in all of Sintra and is the subject of endless speculation and fascination for those interested in the Knights Templar. A puzzling maze of underground passageways connecting caves and wells that resemble subterranean towers, the Initiation Well is a must-see when visiting Sintra.

According to an article published by the BBC, Templar initiations at Quinta da Regaleira began with candidates entering the Initiation Well blindfolded. Holding a sword close to their heart, they would descend nine flights of stairs, the number representing the nine founders of the Templar order. Once reaching the bottom of the well, the candidate would walk into a dark labyrinth where he would symbolically and literally find his way up towards the light. If he was able to make it back through the well tower and into the sunlight, the initiate would walk across stones in water to reach the chapel where he would then be welcomed into the brotherhood.

A puzzling labyrinth of underground passageways connecting caves and wells that resemble subterranean towers, Quinta da Regaleira is a must-see when visiting Sintra.

Fascinating to imagine? Yes. Purely speculative? Yes! In short, Quinta da Regaleira was built as an escape from reality. God bless wealthy eccentrics, y’all!

The setting of a thousand years of history, Sintra National Palace was founded under Arab rule and is the sole survivor of Portugal’s medieval palaces.

4. Sintra National Palace. The setting of a thousand years of history, Sintra National Palace was founded under Arab rule and is the sole survivor of Portugal’s medieval palaces. Surprisingly, it has basically remained unchanged since the 16th century. Inhabited for nearly eight centuries by the Portuguese monarchy, all of the rooms remain furnished and very well-preserved. The largest of all the rooms, the Swan Room is a highlight of any visit.

A highlight of any visit is the Swan Room, the largest of all the rooms.

Massive, historic and beautiful, Sintra National Palace should definitely be on your list. Another compelling reason to visit: It’s convenient! Unlike some of the other palaces, it is not perched on top of a mountain or dangling over the edge of a cliff. It’s located smack in the middle of the historic town center, making for an easy walk from the train station.

One of the last great Rococo buildings to be designed in Europe, the National Palace of Queluz and its historical gardens are remarkable.

5. National Palace of Queluz. One of the last great Rococo buildings to be designed in Europe, the National Palace of Queluz and its historical gardens are remarkable. Built as a summer retreat, it was used as a discreet location to confine Queen Maria as she descended into madness.

So, that’s it. Those are my five favorite fairytale castles in Portugal! Other blockbuster attractions include Palace Duques de Bragança, the Moorish Castle and the Palace of Monserrate. And don’t worry. You certainly won’t starve to death while castle-hopping. Portugal has some of the most incredible cuisine on this Earth! All along the way, you’ll find plenty of charming cafes, wonderful restaurants and gorgeous wine bars.
Hmmm… a few castles, a little sangria, a comfy guesthouse — I can’t think of a more fabulous fairytale vacation. Can you? x Sandy
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