A Day Trip To Sintra, Portugal: A Week In Portugal V.2

Pena Palace in Sintra, Portugal

Another day, another search for early morning coffee. There was a tour group departing in the lobby and I saw they had a little coffee set-up waaay in the back, so I snookered some coffee from there. I have no idea if this coffee was always here before the breakfast hour, or if I was stealing it from a tour group, but I really didn’t care. No one wants to deal with me pre-coffee. They can fight me for it. And, besides—I need to perk up for my day trip to Sintra, Portugal!


Quinta da Regaleira & Pena Palace In Sintra, Portugal

In typical fashion for this hotel, the coffee spot looked largely neglected by the staff and shit was everywhere—used coffee cups, empty sugar packet trash, all strewn about. There was very little left of pretty much everything, but I’m not too proud. I scrounged the ever-loving hell out of that cup of coffee.

Our Sintra, Portugal tour company emailed me that they’d be running late for pick-up. Our guide, Philippe, was flustered upon arrival and opened the door to the van to let us in, only to find it wasn’t his van. We drove around the city doing a couple of pick-ups and ended up with quite the international group. A young Korean kid, an Australian Muslim kid working in London (Samir), an Indonesian girl working in Paris, and a young Romanian couple expecting their first child. 

Not Part Of “The In Crowd” Anymore…

There are a couple of countries the natives are beyond excited that you’ve visited, and Romania is one of them. In my experience, Romanians are usually shocked and grateful when they hear you’ve visited their country… and liked it. Like… super happy, or I wouldn’t even mention it. Bosnians are another group. The woman of the couple was actually from Transylvania, which is a particularly cool area. 

At any rate, given our crowd, it started to dawn on me that I’m no longer the young, energetic traveler that I once was. But I am so excited and happy that these kids are out discovering the world, most of them solo. And they just seemed like really nice people.

They would later be planning drinks that evening and getting some food together. …I am no longer part of the cool kid crowd and did not receive an invitation. Nor did my dad. Little did they know I could probably teach them a thing or two about Global Debauchery. Just sayin…


If you’re a first-time Gate 1 customer, you’re eligible to receive $50 off an escorted tour to Portugal. (Or any other country they offer escorted tours in.) Just provide them my name and account number when booking and voila! Reach out via the Contact form, if interested, and I can provide you the necessary info.

The Microclimate That Is Sintra, Portugal

Now, Philippe told us that Sintra, Portugal is actually a microclimate, but I didn’t truly understand what that meant until we got there. What it meant was that, while it’s 90 degrees every day in Lisbon, it’s cold, rainy, and so foggy you can’t see fifty feet in front of you in Sintra.

We couldn’t see Pena Palace at all until we actually went there later that afternoon. Pena Palace is fairly famous and, if you admire travel photos at all, you’ve probably seen this one—a bright red and yellow tiered fairytale castle in the mountains of Portugal. If you get a good day, there’s incredibly picturesque views from all angles of it, but… not for us on this day.  

Slick Cobbles & Pillow Pastry In Sintra, Portugal

The town of Sintra, Portugal—our first stop—is in the mountains and, periodically, in the little streets, they have intricate little fountains with spring water that you can just drink straight from. It’s a small little town and, given the dampness, the cobbles were super, super slick.

Philippe recommended we try the famous Sintra pastry in town, the “travesseiro.” My dad and I already had a good breakfast and has initially opted out, but the kids told us we absolutely had to try one, so we did. I didn’t regret it. Good thing about having some youngsters there to encourage you. Travesseiro translates to “large pillow” and it’s a rectangular, flaky pastry of almonds and cream with sugar on top. Dreamy.

Sintra, Portugal’s Fairytale Home, Quinta Da Regaleira

Next up was Quinta da Regaleira. This spot is a super impressive mansion with gorgeous gardens. Also very fairytale-like. Lots of incredible details in the Manueline style, a big architectural style in Portugal. There’s an amazing staircase there that I was looking forward to taking a picture of.

Supposedly, the owner way back when was part of the Free Masons and a bunch of the features in the gardens were built in the name of the Free Masons, the staircase being one of them. Philippe mentioned the Illuminati here, like… legit Illuminati. So weird. Super secret society.

Car Accidents & Chaos

Our next two stops were a bit of a let down—Cabo da Roca and Cascais. The drive over was a solid half hour on super winding roads. The guide told us to let him know at any time if anyone was feeling car sick. …We were in the back row. But all was fine.

About halfway through the drive, the van slammed on its brakes and I heard a loud crack in front of us. A car had stopped super quickly and the car behind it (the one directly in front of us) rear ended the shit out of the first guy. When everyone got out of their cars, the first guy turned out to be a super old man. So sad, but he seemed okay.

Adding to the chaos was a dog barking like crazy, so initially, I thought someone braked for a dog and maybe it got hit. Thankfully, no. The dog was fenced in on the side of the road. But it was total chaos for a few minutes. Continuing on…

Cascais, Portugal

Quick Stops In Cabo Da Roca & Cascais

Cabo da Roca is a gorgeous cape with lots of cliffs over the ocean. Lots of surfers come here. But, when we got there, it was completely mobbed with bikers. Yes, bikers. And there was so much fog, you couldn’t get a very good view. Too bad because it looks incredible.

Cascais is a really lovely little seaside resort town. Really colorful, cobbled streets, enclosed little beach. The town itself wasn’t a letdown, but the timing was. We only had an hour and we had to get lunch while we were there. Found a small Irish pub that didn’t look mobbed and grabbed some fish and chips. Super adventurous and super Portuguese, I know. But we were on a time crunch. 

Pena Palace, The Highlight Of Sintra, Portugal

Last, but not least, was Pena Palace. We drove back to the Sintra area for the afternoon and made the hilly hike up to the palace. It looked really beautiful, but it was Sunday and there were so many people. Also really foggy. And raining on our hike.

Lots of yellow and red and—my favorite part—it had a chapel steeple that was green, black and white tile. Just a really nice detail on the red and yellow castle. I guess one color of the castle was a monastery and the other color was the castle part way back in the day. 

Lisbon’s Time Out Market & Our Portuguese Dinner

On the drive back, Samir told us about “Time Out.” I had zero idea what this was and he looked at me a little quizzically. Yes. I’m old and out of touch. I’m embarrassed. But he was super kind about it. Supposedly, it’s a magazine. But it has a spin-off concept of marketplaces filled with Michelin-starred chefs. And, wouldn’t you know, they happen to have a Time Out Market right here in Lisbon.

We wouldn’t make our way there that night because… we’re old, but we did stop by a Yelp place a couple of blocks over with lots of stairs on the way—Restaurante Duque. Small place, decent food. Tomorrow, we’ll be exploring more of Lisbon, on foot this time. Looking forward to digging in.

Lisbon’s Alfama & Bairro Alto Districts

So, today was a mixed bag. We walked up into Alfama (Old Town). So many stairs, so many hills. Our first stop was Castelo de San Jorge, the big castle that overlooks Lisbon. Wouldn’t you know the entrance Google Maps takes you to was closed, so we had to do even more walking to get to the other side. Nice views of the city and a fun, quick little exploration. Funny enough, we ran into Samir almost as soon as we got there, who told us all about how Time Out was and that we should definitely check it out.

Churches & Coffee, Miradouros & Lunch

Our next stops were Sao Vicente de Fora and Santa Engracia (two churches that were supposed to have great interiors), but… both were closed. We’d learn the next day that everything in Lisbon is closed on Mondays, which sucks since both locations were about a mile walk each. Probably something I should’ve researched before we walked all the hell the way out. I’m such an amateur. On the upside, we did stop at a little park with some nice street art and grab some coffee on the way. Ended up Ubering back to Alfama to save some energy.

Stopped off at the Santa Luzia miradouro (a picturesque city viewpoint)—which we’d actually already been past, but didn’t know at the time—and decided to grab lunch. Super tasty. My dad got a caprese salad with a homemade iced tea, which he thought was delicious. I got some sort of traditional garlicky beef dish. Also delicious. 

The Street Art of Bairro Alto

Made our way over to the Bairro Alto district to see Igreja do Carmo, some ruins that were supposed to be super cool. Not sure whether this was open or not, but we didn’t ultimately end up going in. It didn’t look like much on the outside, but when I Googled it later, it was something I’d wanted to see. Oh well. 

Finished the day with a stroll through some Botanical Gardens (of which there are many in Lisbon). Getting there was yet another hike and a wrong turn on my part took us through a really cool street art area. When we got back on track, Google Maps had taken us to another closed entrance. Pretty place, though. Once we finally got there. 

Dinner was a sad Uber Eats order. So tired. Overall, not the best touring day I’ve ever had, but I was glad to get out and about and on the ground in Lisbon. There are so many hills. And it’s so hot. I can’t say that enough. Another day trip tomorrow to explore some medieval villages.

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