Cascais: Our Final Stop in Portugal

After three and a half weeks in Lagos, Carla and I packed up our considerably lighter collection of belongings and headed about three hours north to Cascais, a coastal town roughly 30 kilometers west of Lisbon.

And Cascais is beautiful. Really beautiful. It sits along what is often called the Portuguese Riviera, and it doesn’t take long to understand how it earned the description. Elegant buildings, manicured streets, beaches, restaurants, a lovely waterfront, and the kind of polished appearance that suggests the town has been practicing being attractive for quite some time.

Which, as it turns out, it has. For much of its early history, Cascais was primarily a fishing and farming community. Then, in the late 1800s, King Luís I and the Portuguese royal family began spending their summers here. Royal families have a way of attracting neighbors.

Soon the Portuguese nobility followed, building mansions and summer homes, and Cascais gradually transformed itself from a quiet fishing village into a fashionable seaside retreat. Wealthy families from Portugal and elsewhere began arriving, and over time the town became known as a playground for aristocrats.

You can still feel some of that today. There’s an elegance to Cascais. Everything seems rather well cared for. The town feels safe and comfortable. The restaurants are excellent. The climate is wonderful. Lisbon is close enough that you have a major European capital practically next door, and there’s a sizable international community of people who have decided this is a pretty good place to call home.

They have a point.

So why were Carla and I there? Fair question. Cascais isn’t exactly the kind of place we normally gravitate toward. We tend to like places with a few more rough edges - some grit, a little unpredictability, perhaps a building or two badly in need of paint.

Cascais looked as though someone had already taken care of all that. But because it repeatedly appears on lists of desirable places to live in Portugal, particularly for people coming from elsewhere, we thought it deserved a look.

And I’m glad we came. We genuinely enjoyed it.

That’s one of the interesting things we’re discovering as we think about where we might someday live: loving a place and wanting to live there are not necessarily the same thing.

Cascais is unquestionably appealing. But after a few days, both Carla and I had more or less arrived at the same conclusion. It wasn’t our place. There was nothing particularly wrong with it. Quite the opposite. It checked an impressive number of boxes.But human beings apparently cannot be reduced entirely to boxes.

There’s that other thing. Feeling. Does somewhere stir you? Do you feel curious when you walk out the door? Does the place seem to speak a language that, even if you can’t quite translate it, you somehow understand?

Cascais didn’t do that for us.

And then there was the small matter of cost. Cascais has become one of the more desirable - and consequently more expensive - places to live in Portugal. Even if we had fallen completely in love with it, the kind of lifestyle we want would have been considerably more expensive there than in some of the other places we were exploring.

So after five days, we said goodbye. And then we did something we hadn’t originally planned to do. We left Portugal.

Our intention had been to spend three months exploring the country, looking carefully at different places and asking ourselves whether one of them might eventually become home. Instead, we cut that journey short by roughly two months and boarded a red-eye flight from Lisbon to Greece.

Sometimes travel plans change because something goes wrong. Ours changed because something simply wasn’t going quite right. Portugal had been very good to us. We’d eaten wonderful food, met lovely people, walked magnificent coastlines, and spent time in places we genuinely enjoyed.

There was no great disappointment. No dramatic moment when we looked at one another and declared Portugal a terrible mistake. Nothing remotely like that.

We simply weren’t feeling the connection we had hoped to feel. And that matters.

Especially when you’re not just choosing somewhere for a vacation. We were asking whether we could imagine making a life there. That requires something more.

So we followed the feeling. And now we’re in Chania, on the Greek island of Crete.

We’ve been here only a few days, and already something feels different. Sometimes you can spend weeks trying to convince yourself that a place should work. Then you arrive somewhere else and your body answers the question before your brain has finished asking it.

Chania did that to us. We walked into the old town and almost immediately felt drawn in. The Venetian harbor. The narrow streets. The layers of history. The old buildings leaning into one another. The sea. The cafes. The light. The life happening everywhere around us.

Beauty certainly has something to do with it, but we’ve seen plenty of beautiful places. This felt like more than beauty. It felt like connection. And that’s difficult to quantify. There’s no column for it on a relocation spreadsheet.

Weather: excellent.

Walkability: excellent.

Healthcare: good.

Airport access: acceptable.

Inexplicable feeling that you somehow belong here: apparently not available as a sortable category.

And yet that last one may ultimately matter as much as anything else. We’ll spend the next couple of weeks in Chania before continuing on to Naxos, Corfu, and eventually Athens, giving ourselves about two months in Greece altogether.

We have no idea what we’ll discover.

That’s the fun part.Maybe somewhere ahead is the place that makes us say, This is it. Maybe not.

Perhaps the larger lesson is simply that you can’t force yourself to fall in love with a place because the practical advantages look good on paper. Portugal made sense to us. In many ways, it still does.

But Greece, almost immediately, made us feel something. And increasingly, I think this entire search is going to require both.

A place has to work. But it also has to move us. Cascais reminded us of that. It was beautiful. Elegant. Comfortable. A place we were very glad to experience.

It simply wasn’t ours. And sometimes discovering where you don’t belong brings you one step closer to finding where you do.