Sintra, Portugal—A Fairytale Come to Life

Oh, Sintra. Magical, enchanting, and straight out of a fairytale. I half-expected fairies and elves to greet us at every turn as the delicate white floaty things (the ones that drift in the wind, like they’re sprinkled by some invisible pixie?) danced around us. From the moment we arrived, I felt like I was in a dream…no, really, it was surreal. To be honest, Sintra was the top place I was itching to visit in Portugal. And it hit, let me tell you.

People always ask me what my favorite places and experiences are, and honestly, it’s nearly impossible to choose. I’ve been to almost 70 countries, thousands of cities, countless historical landmarks, cathedrals, wats, and natural wonders; each with its own special kind of magic. That said, a few standouts come to mind:

The Taj Mahal: Nothing prepares you for seeing it in person. The sheer magic and deep history blew me away.
Machu Picchu: Hiking the four-day Inca Trail to get there (during the rainy season, no less) was one of the most challenging and rewarding experiences of my life.
Base Jumping over the Swiss Alps: Jumping out of a helicopter over the Alps? Yeah, that ranks high. It was like flying—exhilarating and terrifying in the best way.
Slow Boating Down the Mekong Delta: The blend of culture, calm, and chaos makes this a one-of-a-kind experience.
Cinque Terre, Italy: Those colorful villages perched on cliffs along the coast? It’s like a postcard came to life. Hiking between towns and drinking local wine with sea views—can’t beat that.
Hiking Up and Sledding Down a Volcano in Bariloche, Patagonia: Yes, sledding down a volcano. It’s as insane and incredible as it sounds. Hiking up is tough, but zooming down on a sled? Next level.
Hiring “The Easy Riders” in Vietnam: I hired a motorcycle group to take me to my Dad’s bunker from the American War in Vietnam. Personal, emotional, and one for the books. Dad was supposed to join me in this pilgrimage of sorts but wasn’t able to make it.
Being Chased by Elephants in Botswana: The wilderness gets real when you’re being pursued by elephants. Add hippos raiding my campsite in Namibia for good measure—wild times.
Scuba Diving in Thailand, the Great Barrier Reef, and Belize: I’ve done some amazing dives around the world, but nothing compares to the liveaboard dive trip through Thailand’s Similan Islands or spending New Year’s Eve on the Great Barrier Reef. Best dive of my life. Oh, and the Blue Hole in Belize? Jaw-dropping.
Watching Lava Flow into the Ocean in Hawaii: Seeing a volcano erupt in real-time from a boat, with lava flowing into the ocean? One of the most surreal and unforgettable experiences ever.
Being Chased by Locals Wielding Machetes: Not exactly a top experience, more of a complete shit show of horror, but hey, it’s worth mentioning for the WTF factor.

And now, I can officially add Sintra to this list. There’s something otherworldly about it; like stepping into a fable. Between the misty forests, grand palaces, and enchanting atmosphere, it’s easily one of the most magical places I’ve ever been. I felt like I’d time-traveled to another realm.

It’s not just the jaw-dropping beauty. It’s the vibe here. The ancient history, the diversity of the landscapes, the culture, and the crazy thing is that once you step into Sintra’s bubble, the outside world just ceases to exist. You’re in this otherworldly place where the only thing that matters is what’s right in front of you. It’s like Alice’s Wonderland but even cooler—and Sintra really does love its Cheshire-like cats. I am still confused why there is so much art dedicated to cats here. Someone explain please.

Now, instead of staying right in Sintra, we decided to opt for a more personal experience—a cozy bed-and-breakfast-style home stay with a local Portuguese family. And wow. Their property was an absolute dream! Acres of lush, mystical forest with sweeping views of Sintra’s three main palaces. It was like being in a storybook. The place itself had this incredible old-world vibe, covered in vines and history. The family, led by the lovely Ines, welcomed us with open arms, and they even had their kids helping out with the hospitality (Yassssss).

Our breakfast spot each morning was a cozy little table for two on the deck, surrounded by nature, with sweeping views for days. Fresh eggs from their own chickens, homemade bread, juice, and coffee. It was perfection. The guest house we stayed in was basically a full-blown apartment, complete with a living room, a cozy bed, a kitchen, and these adorable windows that opened to the most breathtaking views. It was just us, the beautiful family, and the kind of tranquility you can only dream of. It quickly made the Évora hotel experience a thing of the past.

You can walk to the castles from here—it’s about 30 minutes through these enchanting forest paths. We loved the adventure, and honestly, the whole experience felt like we’d stumbled into some sort of magical hideaway. If you ever find yourself in Sintra and want something special, book this place. Thank you, Ines and family, for making us feel like royalty. Here’s the link to their stunning property—trust me, you won’t regret it: Airbnb Listing.

Sintra Town

Sintra town is absolutely captivating, bursting with energy and charm at every turn. The narrow, steep streets are packed with local boutiques selling everything from handcrafted jewelry to colorful Portuguese tiles, unique clothing, and every kind of souvenir you could ever dream of. It’s like stepping into a postcard…until you’re driving, that is. Trust me, if you get stuck on the wrong one-way street, you’ll find yourself in a never-ending loop around the castles that adds 20 minutes to your trip each time. Just ask us how we know—yeah, we got caught in that maze more than once! ( Sorry Honey! My bad)

But the detours were all part of the adventure, aren’t they always? It all about the journey, not the destination (or so they say, ha).

The town itself feels like a blend of old-world charm buzzing with warm energy. Portuguse pastelarias, gelato spots, wine bars, and restaurants line the streets, serving up everything from local delicacies to the best damn lasagna we’ve ever had. No joke, it was that good.Now, mind you it was at an Italian restaurant, but the food was superb The frommagio bread still has me drooling. We’re talking cheesy, melt-in-your-mouth perfection that you wouldn’t expect to find in Portugal, but there it was, blowing our minds in the middle of this historic town.

The city center opens up to a plaza with stunning views of the Palácio Nacional de Sintra . As we devoured a plate of cheese and charcuterie and sipped on my new favorite, Vinho Verde, live musicians serenaded the crowd. The ambiance was on point. This place has…yup, you guessed it, a vibe, babe.

The local Sopa de legumes (simple vegetable soup) was also out of this world—I loved it so much I went back the next day for round two.

There’s something about Sintra that makes every experience feel a little more magical, even if you’re just walking down the street or sipping a glass of wine. You feel like you’re part of an old story, and honestly, it’s hard to put into words just how special this place is.

The Palaces & Castles We Visited

Pena Palace

Perched high up in the hills of Sintra, this vibrant palace boasts an cornucopia mix of yellows, reds, and blues. Wandering around, you get this mash-up of architectural styles. The views from the palace are next-level. You’re looking out over all of Sintra, the forests, the ocean in the distance. It’s surreal. It’s like stepping into a dreamscape. The palace is also a UNESCO World Heritage Site (You know how much we love those).

“Built in the mid-19th century, Pena Palace is one of the most important examples of Romanticism in Portugal, commissioned by King Ferdinand II. Originally a monastery in ruins, King Ferdinand decided to transform it into a royal summer residence. The palace’s eclectic mix of architectural styles—Gothic, Renaissance, Moorish, and Manueline—is a reflection of the Romantic spirit of the time.” Information taken from this site.

We loved wondering around the palace grounds and gardens, discovering unique and colorful finds around every nook and cranny. We took our time and explored the entire grounds and palace itself.

Getting into the palace was an experience in itself. The line to get inside was like a theme park ride. It was long and winding, and we were packed in tighter than the sardines they love so much here in Portugal. Honestly, the whole one-way shuffle through a maze of rooms, with zero personal space, wasn’t my favorite. I’d have been just as happy exploring the outside and palace grounds. But, once inside, the rooms were insanely ornate—jaw-dropping detail in every corner.

My personal highlight? The moment I touched one of the canopy beds and got absolutely screamed at by the security guard. Honey was mortified. I swear I didn’t even realize I was touching it until I heard the security guard shouting at me. Oops. Total instinct. Sorry Honey, once again, my bad.

Moorish Castle

This one’s old…like, 8th-century old, built by the Moors when they were ruling Portugal. It’s perched up on the Sintra hills because for defense purposes. Honey sat this one out so I was on my own to explore. She was still under the weather and didn’t feel like trekking all the way there and then climbing the thousands of steps. I get it, believe me.

The wind was whirling, whistling and whipping me and my hair around like crazy but it was absolutely energizing to be in that place. I could FEEL the energy pumping through me and I felt so…alive. It was a social and unique experience, one that I will never forget. I loved this place. It was damp, cold, and misting, it was giving me Game of Thrones vibes.

Did you know that Sintra literally has its own micro climate? I just found that out and it truly is remarkable is just a few miles away the sun was shining, no wind, and it was about 20 degrees warmer.

The Moorish Castle is one of those places where you can practically feel the centuries of history under your feet, and the views were absolutely killer.

Quinta da Regaleira

This place is basically the playground of António Augusto Carvalho Monteiro, a super rich guy with a thing for alchemy, Freemasonry, and Knights Templar conspiracies (sound like my kind of dude).

Built between 1904 and 1910, he turned it into a massive estate full of secret tunnels, hidden symbols, and the iconic Initiation Well, which people say represents a journey of self-discovery. It’s a mix of Gothic, Renaissance, and Manueline architecture, and it feels like you’re literally walking through a Da Vinci Code novel.

The Initiation Well was the top site for us in Quinta da Regaleira. It isn’t just some ordinary well. It’s more like a mystical spiral staircase that descends deep into the earth. We learned that was never meant to hold water but instead served as a symbol for secret rituals, representing a journey into the depths of the soul. (First Chapel of Bones, now this? Weird, awesome, and creepy. We love it.) You can walk down the winding stairs, and basically descend into another world, with each step revealing more of its mystery.