We were barely awake when we rolled out of the Moxy Lisbon City at 6:45AM—one of those mornings where the sky is still deciding what color it wants to be and you’re already negotiating with your legs about the day ahead. By 7:00, we were clutching caffeine at a Starbucks in downtown Lisbon, quietly pretending we were energetic people.
The drive to Sintra felt like slipping into another world—misty hills, winding roads, and that slightly ominous “you’re about to climb something” energy. We pulled into what looked like a victory parking spot—third car in the closest lot. Felt smug for about 12 seconds.
Then we asked where Pena Palace was. The woman didn’t speak. She just pointed… up.
And that was it. That was the moment our day turned into a StairMaster documentary. I will tell you Kellie never once said anything about the totality of my blunder of ‘the walk’. She was actually proud of her fit level, so was I:) This was very reminiscent of the Pilgrimage hike Justin and I did on the Kansai Peninsula in Japan a few years ago.
There’s something humbling about realizing a palace was deliberately built on top of a mountain. Not a hill. A statement. We started up the wooded path, and it just… kept going. Forty-five minutes, 5,000+ steps, 51 flights—before 9:00AM. Before breakfast had even decided if it wanted to stay with us.
Somewhere around step 3,200, I’m pretty sure we entered a different time period.
And honestly, it makes sense. Pena Palace was built in the 1800s by King Ferdinand II as a Romanticist fever dream—bright colors, wild architecture, mixing Gothic, Moorish, and Renaissance styles like he just couldn’t pick a favorite. It’s basically Europe’s most extravagant Pinterest board.
Inside, it feels like royalty lived there… but also maybe got lost a few times.
Outside, the views stretch forever—if you can catch your breath long enough to notice.
From there, we wandered down through the Castle of the Moors, which is older, moodier, and built by the Moors in the 8th–9th century. It’s all stone walls and dramatic ridgelines—like something out of a fantasy movie where someone is definitely about to defend something.
By the time we reached Sintra Historic Center, we had earned lunch in a way that felt deeply personal. Quick shopping, food that disappeared faster than it arrived, and a brief moment where we considered not going back uphill again.
We did it anyway.
Back up we went to Quinta da Regaleira—which feels less like a property and more like someone built a secret society playground and forgot to explain it.
The highlight: the Initiation Well. A spiraling, underground tower that looks like it was designed for mysterious rituals—and actually kind of was. It ties into Masonic symbolism and initiation rites, because apparently regular gardens weren’t interesting enough.
Walking down into it feels like descending into a story you don’t fully understand but are happy to be part of. The caves, tunnels, hidden pathways—it’s all slightly surreal, like Sintra decided to lean fully into being magical and never looked back.
Eventually—eventually—we made it back to the car, legs officially filing complaints. The drive out to Praia D’El Rey Marriott Golf & Beach Resort felt like a slow exhale.
We walked down to the beach where the Atlantic was putting on a full performance—big waves, endless horizon, that salty air that makes everything feel earned. After a day of climbing castles, standing still felt like an achievement.
Dinner was one of those meals where you don’t say much because everyone’s too tired and too happy. And then the hot tub. And the sauna. And that moment where your legs finally forgive you… a little.