Category: Travel & Inspiration

My son had a school vacation week, I needed sunshine, and because I’m the kind of person who genuinely loves her job, I don’t feel the need to separate “vacation” and “work” into tidy boxes. My balance comes from blending both — even abroad.

So I created a plan. It was lovely, optimistic, almost poetic.

And then reality said: sweetheart… sit down.

When the First Cracks Appeared

The first morning, things were already slipping away from the plan. A client began emailing my team asking for an update — nothing urgent, nothing dramatic, but something I wanted to answer myself. After all, I was going to answer… just not right that second.

Cue that familiar internal spiral: “No one reply. Please no one reply. Please let me handle this…”

It was 10 AM, and we were at Praça do Comércio meeting our guide and the rest of the group while I was frantically messaging both the team and the client. Then I realized my phone battery was dying. I had carried my faithful powerbank… but had left the connecting cable in the hotel room.

The result? I spent the rest of the day running around Lisbon begging various shops, cafés, and bars to let me charge my phone using my laptop charger. Not exactly the breezy “remote-work goddess” aesthetic I had planned.

The Day Sintra Tried to Drown Us

Pouring, sideways, merciless rain — the kind that instantly turns any teenager’s mood into “Why have you done this to me?”

So much for sunshine and idyllic mother–son bonding.

Eventually, when the Sintra rain finally defeated me, I surrendered to my son’s request to go back early. But once we returned, I got a couple of quiet hours of work in the hotel room while he relaxed on his phone. A small victory.

The Broadcasting Communication Incident

Somewhere between all of this, Microsoft Azure experienced a widespread outage — meaning my colleagues and I had to align how to communicate this to clients.

Of course it happened from inside a minivan on a tour. Of course.

Pockets of Working Time

To my own surprise, I was more productive than expected.

Maybe because my expectations were low. Maybe because he’s older now and wonderfully understanding. Probably because after years of working remotely, I know my own rhythm.

Airports were a blessing. I arrive ridiculously early for peace of mind, which meant I worked calmly while my son explored the shops — both on departure and return. A surprising amount of clarity can happen near Gate 23.

Mornings in Lisbon were perfect thanks to the time zone difference. My 9 AM meetings magically became 8 AM, and I took them wherever we happened to be: the hotel room, cafés, even once on a park bench — the kind of moment that makes you look charmingly bohemian and slightly unhinged.

And then there were the long stretches in the minivan during our full-day tour to Fátima, Nazaré, and Óbidos. While my son gazed out the window, I slid into work mode. There’s something satisfying about clearing tasks while someone else drives you through cliffs and ocean views.

Meetings were mostly fine — connectivity was decent, noise manageable, the hotel lobby becoming my temporary office when the room signal failed me.

The only real crisis was the infamous cable incident. A powerbank without a cable is just a heavy rectangle.

That day, my phone battery dictated my movements more than the Lisbon tram map.

But beyond that? Working went smoothly because I’d already warned everyone it was my “week abroad working part-time.” My colleagues were kind, flexible, and protective of my focus.

Being a Remote-Working Mom… Abroad

My son carried my laptop in his backpack everywhere — wrapped in not one, but two plastic bags. (My intuition said “protect it from your teenager,” and intuition was right. When the Sintra monsoon arrived, I silently thanked past-me for this moment of maternal paranoia.)

He handled the whole trip beautifully. Curious, patient, engaged. And only mildly annoyed during:

• the client-email frenzy
• the Azure downtime inside the minivan

The rest of the time, he was wonderfully independent — sometimes goofy, always hungry.

And then came my favorite moments:

• his joyful smile when the amphibious vehicle plunged from land into the river
• watching him chat in English with a man from Philadelphia about the Philly sandwich
• trying to keep him from getting too close to the cliffs of Nazaré

Stressful Moments… and the Joy That Outweighed Them

Yes, the client email stressed me. Yes, the Azure outage stressed me. Yes, the cable fiasco nearly broke me.

But the joy? The joy was richer.

The food — oh, the food. The sunshine (when we had it). His excitement. The guides who made Lisbon sparkle.

He wasn’t bored. He wasn’t complaining. He was genuinely enjoying Lisbon, the experience, and our funny little routine.

What I’d Do Differently Next Time

Bring every possible charging cable. Obviously.

And treat the weather forecast as a serious warning instead of a polite suggestion. Coming from Belgium, I thought I knew rain. I did not know that rain.

What This Trip Taught Me

Workations with a child are a dance of compromise, patience, humor, snacks, and occasionally… bribery.

He earned a Benfica T-shirt and a Sporting one for excellent behavior — proof that dual-team diplomacy can work.

Workations aren’t about balance. They’re about adaptation.

So, Was It Worth It?

Absolutely.

Not because it was perfect — it wasn’t.

But because it was ours. Messy, funny, demanding, warm, challenging, delicious, rainy, joyful, surprising.

Exactly the kind of trip that becomes a memory.

Honest Recommendations

Before I dive into the list, just a note: these are simply the places and brands I genuinely enjoyed on this trip. None of them know I’m mentioning them, and nothing here is sponsored.

• Lisbon Riders — Our guide Carolina was fantastic. The mix of Fátima, Nazaré, and Óbidos was perfect, and sitting in the back of the van was comfortable enough for me to get some work done between stops.

• Street Buddha – True Portuguese Soul Tour — Igor was enthusiastic and passionate, sharing his neighborhood, stories, and street-art love with us. My son absolutely looked up to him as this cool, art-loving local.

• HIPPOtrip — A totally unique way to see the city. More entertainer than guide, our host had us singing, laughing, and enjoying the ride as the amphibious vehicle moved from land to water.

• Doca de Santo — The polvo assado did not disappoint. It didn’t feel touristy — I’d definitely go back.

• Colonial cuisines — Just like London shines with Indian food and Paris with Vietnamese, Lisbon has incredible spots from its former colonies. After our fair share of Portuguese food, we dove into Mozambican (Cantinho do Aziz) and Brazilian flavors (Acarajé da Carol) — both excellent.

• Traveling mum tip — I’m a huge fan of my beloved cross-body bag, where my phone, headphones, powerbank, etc. all fit securely. A small thing that makes a big difference.

Final Thoughts

In the end, this workation reminded me that trips don’t need to be flawless to be meaningful. They just need to be lived fully, with all the mishaps, laughter, lessons, and little bursts of joy along the way. And this one? It gave us plenty of each.

💬And now I want to hear from you…
Have you ever tried a workation (or traveled with your kids while working)? I’d love to hear your funniest, most chaotic, or most surprising moment!

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💻 About the Workation Diva
I’m Caro, an early pioneer of remote work, studying IT in the ’90s when “the Internet” still made dial-up noises. I’ve been blending work and travel since before it was fashionable, from spa weekends during business trips to half-vacations at my family’s place in Buenos Aires. These days, I live the part-time laptop lifestyle — balancing motherhood, projects, and plane tickets, proving that freedom can come in Wi-Fi and family-size portions.