The kids were bubbling with excitement as we checked into our hotel the night before. They dashed into the room with the bunk beds and claimed it as their own in a heartbeat. They climbed in eagerly, only to be met with disappointment: a steady drip from the ceiling had soaked the upper bunk bed, and even the lower bed was damp. The front desk did not have any other comparable room to offer. We ended up on the couch, and any attempt to resolve things with the front desk the next morning was met with apathy. There was no offer for a discounted stay or even a complimentary breakfast. It was a disappointing start, to say the least, and it set us back a bit the next morning.
Still, we pressed on straight to Sintra. Sintra and Cascais were both summer retreats for the Portuguese royal family. While Cascais offered the royal family the sea, Sintra offered mountains and hills to beat the summer heat. Parking at Sintra attractions is restricted, so we left the car at the nearest mall and hopped on public transport.
Our first stop: the vibrant and whimsical Pena Palace.
Perched dramatically atop a hill, Pena Palace looks like a castle out of a kid’s coloring book. With its bright yellow and red façade and mix of multiple architectural styles, it was truly a sight to behold. The views of the Sintra mountains from up there are just as breathtaking. Commissioned by King Ferdinand and completed in 1847, it served as a royal residence for decades. It’s said that Queen Amélia, the last queen of Portugal, spent her final night in the country here before going into exile.
Cheered by the riot of color and the views, we hopped into a tuk-tuk for our next destination: Quinta da Regaleira. We hadn’t known much about it other than its UNESCO World Heritage designation, but it turned out to be the highlight of the day.
What a place.
Designed by an eccentric Freemason, this estate is part labyrinth, part castle, and entirely wonder. Everything there seems to have a secret, a passage that leads somewhere unexpected, a ground-level structure that reveals another dimension when viewed from a different angle.
The most famous of these is the Initiation Well: a deep spiral staircase that descends into the earth like an inverted tower. Whether it was ever used for real rituals or simply built for enchantment, we’ll never know. It seemed like art at its purest, not built for a purpose, but there to titillate, to enchant, and to question.
We crept down in hushed silence, but the magic didn’t stop there. At the bottom, we found a rough stone path that wound its way through a cave, eventually opening up to a magical waterfall and a sunlit lake. This lake, the caves, and the waterfall seemed to have existed forever, but each element was intentionally crafted for awe.
Secret passages, hidden doors, clock towers, and structures where one level morphs into another, Quinta da Regaleira was less a building and more a riddle. It was, without question, one of the most captivating places we’ve ever explored.
Our final stop was the Monserrate Palace, another Romantic masterpiece with Moorish, Gothic, and Islamic influences. A central fountain served as the focal point of the antechamber, with elaborately arched hallways spreading out like spokes on a wheel. It felt calm and regal, a softer counterpoint to the earlier grandeur.
By then, we were worn out. After a long wait to catch an Uber back to our car, we made one last stop at the mall for a simple dinner, and a sweet reward: travesseiros, a local specialty. These pillowy pastries, filled with almond and egg cream and dusted with sugar, were the perfect end to the day.
We still had a long drive ahead to Albufeira, three hours of excellent roads that we could speed through. It had been a busy day, and we didn’t even realize how quickly time passed as we recounted the highlights together.