The first few entries of this diary are designed to get you caught up to speed with how we got here. As of publishing this article (April 20th), we received our visa.
Entry 1: Winter, Wars, and More
We flew Ryanair out of Wroclaw.
Only direct flight to Lisbon. Not exactly glamorous, but it got us there.
Landed, picked up the rental car, and the first thing that hit me was how close the airport is to everything. Seven minutes from the rental counter to the Sheraton. That’s it. In most European cities the airport is a 45-minute train ride from the center.
Lisbon’s is practically in the city.
Kinda cool actually.
Hotel was nice. Good view. We checked in, got settled, and I remember thinking — OK.
This could work.
We had a late meal in the hotel restaurant and settled in for the night…
Carcavelos
The next morning we drove out to Carcavelos to visit a friend.
He’s someone I’d known through internet circles since about 2016-2017 — back when I was running my first business, a blog that eventually led to two ebooks and a small audience.
Never met in person. Internet friends. Internet is a powerful thing.
He’d been living in Carcavelos for twenty years at that point, married to a local. He was also a client of my staffing agency, HireUA.
The drive out was the first real surprise.
The freeways around Lisbon are four lanes wide. Big, proper motorways.
But they go straight up and straight down, twisting through hills with the kind of gradients you’d expect on a mountain pass. Not a highway. It’s like someone built a freeway on a roller coaster.
Carcavelos itself was different. Beach was beautiful — wide sand, blue water, February sun that made me forget how much I despised the winters in Eastern Europe.
We walked around. It was nice. I didn’t love that there were no bike paths, and that coastal road wasn’t something I could see myself risking my neck to ride on.
But nice and “I could live here” are two different conversations.
Cascais
An Entrepreneurs Organization member I knew had been generous enough to invite us to his apartment over the ocean. Beautiful property. Beautiful area. Cascais has this polished, international feel to it — expats everywhere, good restaurants, European money mixed with old Portuguese charm.
Maryna and I both had high expectations for Cascais.
And at first glance it looked seriously promising.
But there was one major issue.
We wanted a house.
Not an apartment.
A proper home with outdoor space for our daughter to run around. Not an apartment. Not a flat with a balcony. A house.
And the problem was that none of those areas really seemed to click. The houses in the Cascais area required a drive to get anywhere. Literally, you can’t do anything unless you got in a car.
And, I don’t know how to explain it, but if we were going to be in a “city” (I do understand Cascais is obviously not Lisbon), we wanted some walkability.
And it just wasn’t it. I’ve lived abroad for 10 years. I know what clicks with me and what doesn’t. And it just didn’t click with us.
The next day we stayed in Lisbon and did the tourist thing. Walked around Parque Eduardo VII, let the kiddo watch the planes…
Walked around, ate well, took the metro. I wanted to test what daily life would actually feel like if we lived here. Not the vacation version — the Tuesday afternoon version.
The litmus test for me was:
How would I feel with Maryna and our daughter riding this solo, by themselves, at 9pm?
The answer was:
Not terrible…but also, not great.
I know that sounds picky. But we were coming from Wroclaw, which is the 41st safest city in the world (Lisbon is 99th). The trams are clean. The metro in the capital of Warsaw is spotless. Poland’s public transit is truly excellent.
Lisbon’s metro didn’t feel the same. Not dangerous. Just not the same level. And when you have a toddler, and your hands are always busy and “situational awareness” tends to be overridden by screaming and unhappy child…well, it matters.
And really, it’s ironic looking back, writing this over 1 year later. I don’t have a single authentic photo of the metro…probably because my hands were busy elsewhere — and definitely not watching my pockets.
Now, really, I need to stress this — this doesn’t mean Lisbon isn’t safe.
It’s still not the same as walking around downtown Los Angeles at night. But, it’s a major Western European capital city. You won’t get gunned down in cold blood, or beaten for your iPhone, but you do need to watch your pockets and be aware of petty crime.
That said, that wasn’t the dealbreaker…
The dealbreaker was the hills.
Lisbon’s Hills…The Real Problem
I’d heard about Lisbon’s hills. Everyone talks about Lisbon’s hills.
They’re charming.
They’re part of the character.
Sure, maybe if you’re playing tourist for a week, I could see the charm.
For daily life — they’re lunacy.
These aren’t the rolling hills I grew up with in Northern California and San Diego. These are straight-up, 15%-20% gradient climbs on narrow cobblestone streets.
And I kept thinking — how would I push a stroller up this? How would my wife walk to the grocery store and back without it feeling like a workout?
The answer was…you wouldn’t.
You’d drive everywhere.
And driving in Lisbon is its own kind of miserable.
Cascais, Round 2
We took one more trip back out toward Cascais.
This time we drove some of the international schools. We made the assumption we’d try to find a house somewhere and would have to drive. I wanted to see the route, feel the commute, understand what the daily logistics would look like.
And it just simply wasn’t for us.
We booked train tickets to the Algarve.
The tracks were winding. I had no idea trains could turn that much. It was stuffy and hot. Everybody felt a bit nauseous.
The windows looked like a bug war zone.
We pulled into Faro station tired, sweaty, and wondering if this whole Portugal thing had been a mistake.