Lisbon:
Lisbon is the perfect place to wander aimlessly and get lost in a maze of hilly, cobblestone streets. Throw in a bunch of colossal stone churches, historic monasteries, tons of killer miradouros (viewpoints) skirting the city, and inhaling your weight in custard tarts, and your stay here is pretty much complete.
We gave ourselves four days in the city, which was the absolute perfect amount of time to soak up the vibe before mapping our way to the coast.
The Big Kahuna Day Trip: Sintra’s Castle Hype
Sintra is the undisputed heavy hitter of day trips outside of Lisbon, and it’s a super easy 30-minute train ride from the city. Just outside the main town grid sit the famous castles—Palácio da Pena, the Moorish Castle, and Quinta da Regaleira—all highlighted by UNESCO as World Heritage Sites.
To get up to them, you first have to navigate through the main town of Sintra, which is honestly a European Disneyland-like clusterfuck packed with massive hordes of tour buses and package tourists. But once you break free from that main town circus, a real outdoor treat awaits.
The walks around the lush green hills surrounding the palaces were a highlight, and it was killer exercise navigating those massive inclines while taking in the incredible views. Exploring them, I kept thinking to myself: if Tony Montana had owned a castle like this up in the hills of Sintra instead of living out in Miami, he would have been completely protected from the wrath of Sosa. The castles are must-see if you are in Lisbon.
Eating and drinking alcohol seem to be the premier daily activities in Lisbon. If you ask any local for advice on what to do, they rarely point you toward a museum or a historical ruin. Instead, they immediately steer you to their favorite place to eat and drink.
The seafood out here is amazing and unbelievably cheap. Barbie has been on an absolute mission to devour every single octopus caught in the Atlantic Ocean, as long as it’s perfectly grilled and swimming in garlic, olive oil, and a bit of parsley. They serve it up with these incredibly soft boiled potatoes that you can crush with your fork right into the plate to mop up every last drop of that garlic oil.
While we hit up plenty of traditional seafood joints lining the back alleys, our absolute go-to spot was the Time Out Market at Mercado da Ribeira. The place is fantastic—a massive food hall featuring about 30 high-end stalls manned by the top chefs in Lisboa. It was so good we could have easily eaten every single meal there.
In fact, that’s where Barbie had her absolute best grilled octopus experience, courtesy of Chef Marlene Vieira. It was so good she went back for a doubleheader. The big question remains: will flashpacking Barbie pull the trigger on a historic triple-header when we pass back through Lisbon before our flight out to Israel? My money is on yes.
The King of Tarts and the Egg Custard Trap
The signature dessert that is completely ubiquitous in every single bakery around town is a tiny, warm, handheld custard egg tart called a pastéis de nata. They are quite tasty, but a word to the wise: down these bad boys in strict moderation. If you gorge on them, they have the distinct potential to give you a serious case of the runs.
Now, I know the official Loose Stools Index was technically put out to pasture, but let’s just say there were some short-term internal fireworks when I failed to obey my mother’s golden rule of “eat in moderation.” Instead, I leaned hard into my dad’s philosophy of “fuck it, eat what you want” and proceeded to down these succulent little gems every single day. Worth it? Absolutely.
The undisputed king of the Portuguese egg tart is Pastéis de Belém, located about a 15-to-20-minute tram ride outside the city center in the riverside neighborhood of Belém. Going there is a dead ringer for the legendary Café du Monde experience in New Orleans. It has that exact same high-energy, historic atmosphere and classic serving style. I paired my tarts with their super sweet, freshly squeezed OJ, which was the ultimate beverage choice to wash down the sugar. Barbie wasn’t a huge fan of the egg texture, but I thought they were first-rate.
After packing away a few tarts, you can check out the massive monastery right nearby. It was hot as shit outside the day we went—not Southeast Asia humid hot, but still, really damn hot. We opted to pass on the indoor tour, choosing instead to cool out under a shady tree in the nice green park across the street, watching the world go by with the locals while admiring the impressive monastery architecture from a safe, breezy distance.
Chiado Neighborhood: Living Like The Honeymooners
Our Airbnb was stationed right in the centrally located Chiado district. The narrow, one-way cobblestone street our apartment sat on felt like a living episode of the old TV show The Honeymooners.
Residents would hang out over the railings and literally converse and yell to each other right across the street from their balconies. The gap was so narrow you could practically reach across to your neighbor’s flat to borrow a stick of butter or a couple of eggs. It was a real trip.
Chiado is easily Lisbon’s trendiest neighborhood—the spot where everyone meets up for a morning espresso, an afternoon shopping stroll, or a pre-dinner drink before hitting the neighboring nightlife strip of Bairro Alto. It was the perfect home base, and once again, Airbnb delivered an amazing, immersive experience. I am thoroughly convinced you simply cannot get that same local feeling staying in a sterile hotel room.
Thru the Binocs:
Portugal has a hilarious architectural quirk that you have to experience to believe: it feels like you can almost never pull a public door open from the inside; you can only push them. It’s one of those small daily physics riddles you just have to get used to. So much for holding a door open for an old lady, because logistically and ergonomically, it’s damn near impossible.
[The Tiny Bathroom Blueprint]
┌───────────────────────────┐
│ [Urinal 3] │
│ [Urinal 2] │
│ [Urinal 1] <───┐ │
├─────────┐ │ │
│ DOOR │ ── PUSHES INTO │
│ (INWARD)│ PISSER #1 │
└─────────┴─────────────────┘
Entering a public bathroom in a local tavern is an entry-level challenge that requires Cirque du Soleil levels of flexibility. Because the bathrooms are uniformly tiny, when you push the entrance door inward, the door literally bangs straight into the back of the guy currently using the urinal closest to the entrance.
There could be three perfectly good urinals lined up in there, but because of the tight clearance, it is physically impossible to squeeze past the first guy to get to the empty spots until he finishes up, zips up, and vacates the premises. It’s a total bathroom standoff!
But hey, that’s all part of the charm. Now, we are officially packing up and heading toward the laid-back fishing villages and beaches on the west coast to get our beach groove on.
The Verdict: One and Done
Don’t get me wrong, Lisbon was great to see, but I honestly just do not understand the massive appeal of this city as a top-tier digital nomad hub to hunker down in long-term. Sure, the food was spectacular and the local people were incredibly nice, but I think one solid visit was more than enough for us. We walked the hills, crushed the tarts, and checked the boxes, but we have no burning desire to return. For our style of slow travel, it’s time to trade the concrete hills for the coastline and the sea.
Big Doug & Barbie Drop Out of Society 