If you check online for a list of “Top Family-Friendly Cities,” you’ll usually find one of three things:

Cities that feel too local, too expensive, or ones that make you think… how is this even on the list?

Lisbon.
Melbourne.
London.
Chiang Mai.
Valencia.

It’s like, yeah!

But also…not necessarily. (We saw Medellín on a list and though we haven’t been there, other Roammies families have said a hard “no”.

There are lists on where to travel with kids, safest cities, etc.

But, none that understand US.

So it got us thinking…

If you live abroad or travel like we do — or you’re thinking about it — how do you actually choose the right city to spend time or set down some temporary roots for your family?

What makes a city not just good for little kids, but good for your kind of family?

Because the reality is not all cities work for families that like to live abroad, travel, and just do life a little bit differently.

As many of you know, Porto, Portugal was not the right city for us.

That being said, we have friends with older kids who love it. And it can be a great place to raise a family.

But for us, it didn’t work.

Mika was too young, and we felt like there just weren’t enough things to do for families with babies.

(This map shows that we literally went everywhere in Porto in the one year we were there. We gave it a solid try.)

Also…

The list goes on.

After living in three cities across three different countries with kids under 4, we realized something:

It’s not about finding the “best” city.

It’s about finding the city that fits your stage and style of life. One where it’s not just nice to visit, but actually livable.

Because at this stage — traveling and living abroad with very young kids — is something those lists don’t account for.

So here’s what actually matters for us right now:

We started wondering why Porto felt so small…and it turns out, it is.

When we compared it to other places we’ve lived, we noticed a pattern:

We feel happiest in cities with close to a million people or more.

To put it into perspective:

Porto’s inner metro area — where we spent most of our time — was under 300,000.

To put that into perspective, just our neighborhood in Bogotá is close to that size.

These aren’t exact apples-to-apples comparisons, but the feeling difference is huge.

Maybe it’s our New York–area roots — but bigger cities give us more options, more flexibility, and more ways to spend a day with young kids.

We almost blamed the weather for how we felt in Portugal. But Bogotá also rains a lot (fun fact: Colombia is actually the rainiest country in the world), and it doesn’t feel nearly as draining.

Why?

Because there are always alternatives.

Rain matters a lot less when a city gives you options.

It also helps to be near an international hub. Porto had strong connections within Europe, but Bogotá feels far more globally connected — which makes a difference when you’re living abroad.

There is nothing worse than handling a toddler and a baby all day…
and then standing in line at an office, only to finally get to the front and realize you’re missing one document.

Portugal felt like this constantly.

And while Colombia definitely has its own bureaucracy, it feels like there’s usually a way to figure things out without feeling completely stuck.

We spoke to one family who chose Colombia in part because the mother already had a Colombian passport. It made the entire transition easier.

(For us, it was similar with Max’s Ecuadorian passport.)

When you have young kids, the last thing you want is more friction.

So it’s not just about where you want to live — it’s about where you already understand (or can realistically navigate) the system.

And what that looks like for your kids, too—whether you’re staying short-term or want the option to stay long-term.

Portugal was affordable.

But that didn’t matter when our income became unstable.

I lost a lot of work when we moved, and it wasn’t easy to replace.
Our visa had restrictions.
Local salaries wouldn’t have covered our existing expenses.

So the question isn’t just: “Is this place cheap?”

It’s:

Can we sustain our life here if something changes?

Because when you have kids, you’re not just optimizing for lifestyle — you’re managing risk.

When you live abroad with young kids, what you’re really looking for is a real support system.

Not just friends — but people you can actually rely on.

Raising little kids is hard. Having someone you can call in an emergency, or somewhere your child can go when you need help, makes all the difference.

In Portugal, we had friends — some of whom showed up for us when we needed it — but those options were limited. And most were other expats, which can make it harder to feel fully integrated.

In Colombia, we have a much larger support system. People we can call on—and people we can show up for, too.

We’re also able to access paid help more easily, which changes day-to-day life in a big way.

(This is part of why, despite perceptions around safety, LATAM can be an incredible place to raise young kids.)

Anyway, this isn’t meant to be a comparison between Colombia and Portugal.

It’s about understanding why certain places work better than others depending on where you are in life.

(Of course, we still compare cities—we did the same with Buenos Aires vs. Bogotá. Hard to beat their subway.)

There are also other factors that matter:

For us, Bogotá checks all of these boxes—and then some.

And yet, it would never show up on a “Top Cities for Families” list.

Maybe your city wouldn’t either.

But when you’re raising young kids abroad, what matters isn’t always obvious.

That doesn’t make it any less important.

Because what works today might not work a year from now.

And that’s kind of the point.

So we’re curious…

What cities would you add?

Why?

They can be random, but they have to make sense.

Help us build the “Top Cities for Digital Nomad Families With Young Kids” list.

Send us an email at [email protected] ✈️