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Families that travel together, stay together; Our Life/Travel Plans With Our New Baby

For most of my twenties and thirties, I was on the road. Backpack strapped to my back, passport filling up with stamps, chasing down the wildest adventure I could find in every corner of the globe. It lead to a crazy life. Visiting every country, completing the Ultimate Explorers Grand Slam, making my fortune. For sure for a long time, that solo mission filled my soul. But life has a funny way of evolving. Fast forward to today, I’m happily married, based in Thailand, and now I have a son, who just turned eight months old. and a new home for my mum, beside us, in Thailand. So what does that mean? End of adventures? I hope not. In fact, that as long as we manage not to kill each other, then Families that travel together, stay together. How will that look? How will that work?

My wife Jaa was a flight attendant when we met. She always dreamt of seeing the world beyond the layovers and terminals. I’d already visited every country on Earth, but for her, it was just beginning. Since we met, she’s been to over 50 countries herself. From desert nights in Jordan to sunsets in Bora Bora, we’ve built a relationship around a lot of travel. And now, with Aidan in tow, we’re building a family around it too.

Our Journey as a Family

Our life is anything but ordinary. For better or worse. We’ve shared (is that the right word?!) countless arguments about my expeditions to the North Pole, or climbing Everest. Being away for so long. Up to 7 and 8 months in the early years.

Jaa and I started out on the road and somehow managed to build a relationship without ever fully settling. Our base now, finally, is in Chiang Mai, Thailand, and we love it here. We have a permanent place in Bangkok too. And both spots suit us. The food, the culture, the people. Thailand is literally Jaa’s home of course, and for it’s home in so many ways.

But reality bites too. And as a foreigner in Thailand, you’re always dancing between visa runs, paperwork, and the next flight. So even with a couple of properties, a routine, and now a baby, I’m still legally and practically ‘nomadic’ in terms of paperwork, insurance, legalities etc. Annoying, but it is what it is.

I didn’t choose this lifestyle because it was easy. I chose it because i’m addicted to the chaos. It’s real, it’s never boring. It’s exciting. It forces us to adapt, to learn, to grow. And suffer sometimes. But to get to do that as a family? It’s nice.

Becoming Parents Won’t Slow Us Down (we hope!)

Aidan was born in late 2024, and I remember wondering how this little person was going to change our world. Would I pause the flights? Sell the backpacks? Start talking about car seats instead of carry-ons?(actually, that last bit we did do!)

The answer was: sort of. We travel differently now, but we didn’t stop. In his first year, Aidan will have traveled visited 4 countries. Thailand, Vietnam, Turkiye, and the Maldives. A pretty solid start. I didn’t visit my 4th country until I was 18 or 19!

He’s taken long-haul flights, crossed time zones, and been pushed around cobbled streets in a travel pram while we hunted down vegan meals and sunset views.

It’s not always smooth. Babies cry on planes. Nap schedules don’t care about border control. But the memories we’re making? They’re already priceless. I look back at a photo of Aidan wrapped up on a bridge in Vietnam and think, “This is it. This is our life.”

Families That Travel Together, Stay Together

When I first started backpacking around the world, way back in 2007, I met a guy who told me “before you marry someone, travel with them. If you can backpack with them, you can marry them”. And it that’s true, then add a mini-me into the equation. If we can make it through that, we can do anything.

There’s something about travel that binds people. Of course you share the beautiful (wonderful cliche) memories. But you also suffer together. You’re knackered together. Grumpy, sick. Tired! When you’re facing the unknown together, whether it’s a missed train, a language barrier, or a beautiful view you never expected, you build something deeper. Stronger. And all of that, together. I did it with Jaa. And now I hope, and plan, for the 3 of us to do it together.

I believe that all this applies even more to families. We don’t have routines like most people. I don’t have a traditional ‘job’. Nor does Jaa. For the next 3 or 4 years, our schedules aren’t dictated by school bells or 9-to-5s. So that gives us a chance to do some epic things. Starting gently with 4 countries this year. And lets see next year, but we have some pretty cool plans.

The theory is that when we’re in a new place, we’re fully present. With each other. Less distractions. No autopilot. Just us, figuring it out together. I hope that will bond us as a family even tighter.

Our “Base” in Thailand. But Still Legally Nomadic!

Eurrrgh. And then there is the real side of it. The legal side. The logisitc side. Right now, for context, I’m currently on a 30-day tourist visa in Thailand! No legal right to live here. Having my marriage visa expire while I was running our charity trip in Pakistan. So here we go.

Having a home in Chiang Mai gives us me a soft landing spot between trips. It’s where I come back to regroup, to reset, to reconnect. But I never stay for too long.

As a foreigner, I have to leave the country every now and then for visa purposes. Add in speaking events, charity cycles, my ultra-race series, and filming obligations, and travel isn’t just a lifestyle, it’s a necessity. And my livelihood.

So do I live in Thailand? Yes. Do I have a Thai passport? Nope. Residency? Nope. Any hope of those? Also nope. Health care? Nope. Right to education for Aidan? Nope.

I’m a libertarian at heart. So I’m not complaining. I know the life I choose. And now Aidan is along for the ride. It motivates me to ensure we can maintain the level of lifestyle we have. I can’t rest on my laurels.

And now, Jaa and Aidan are on the journey too. We plan my calendar around adventure and opportunity, not school breaks or bank holidays. And that flexibility is one of the greatest gifts we can give our son.

Education? We can wait and see how we feel when he’s 3,4,5. For now we’ll make the most of our freedom. But how does it work for his healthcare in these early years too? Thankfully, I found a solution for that too.

The Safety Net Every Nomadic Family Needs

As much as I love our lifestyle, I’d be lying if I said I didn’t worry sometimes. Traveling with a child is no joke. And the one thing I refuse to take chances on now is our health (god, am I getting old!?).

That’s why we can rely on SafetyWing’s Nomad Insurance Complete (all the info, pricing etc HERE). It’s built for people exactly like us. Families without borders, or at least no legal right to those borders! So whether I take beer bathing in Prague, or beach breaks in Vietnam, or visiting family in Europe, I know we’re covered.

The best part? It feels like it was designed with real families in mind. Flexible policies, worldwide protection, and none of the fine print that leaves you stranded when you need help most. If you’re a traveling parent, don’t wing it. Get covered. I’m going to explore how Nomad Insurance Complete works. But knowing that I’m ok now, with Jaa, Aidan and me covered whilst living in Thailand, but then also as we travel. It’s serious peace of mind.

SafetyWing Nomad Insurance Complete – What is it and how it works

Safetywing Nomad Insurance Complete is REAL HEALTH INSURANCE, for pretty much the whole world (read the small print here, it’s pretty amazing tbh). Whether you’re traveling on holiday, or living overseas, or anything. It’s proper health insurance. For cancer, for pregnancy, for whatever. No deductibles. High limit. You’re set for life.

I’m not covered by any travel insurance while i’m based in Thailand. So if something would happen, I’d be screwed. Jaa, as a Thai citizen, is covered for basic government hospitals, as is Aidan. But they’re pretty awful. Whereas private healthcare in Thailand is worldclass. So I need it, for them more than me.

Then the same goes when we travel every other month. Are we covered? On generic travel insurance, through my credit cards sure. But proper healthcare? No. But Safetywing Nomad Insurance Complete allows me that.

So if we hit the road for months on end, which we may do next year, to know we’re covered for everything is everything! So how does it work, and how much does it cost?

Safetywing Nomad Insurance Complete for my lifestyle, or for anyone living overseas. In Thailand, mexico whatever. If you’re 39 or under, it’s $1744 for the complete package. Amazing value.

For me, at 41, it’s $2500. Pricier but still great.

For my whole family

For Jaa, and Aidan and me to be covered for pretty much everything, everywhere it’s about $5kish. You can see the price here:

Not cheap. But proper coverage, for the whole world, for every ailment. That’s legit.

The complete package is real insurance. It includes budget ($300) for yearly annual check-ups, it includes all outpatient stuff too (up to $5k). They’e also now got direct billing (yay!) for bills more than $250.

It also covers maternity (10 month wait, up to $2500), child wellness check-ups, annual physical exams, and emergency dental treatment. Mental health therapy, physiotherapy (up to US $60 per visit, with a maximum of 10 visits per policy year), outpatient visits, diagnostics like X-rays and blood tests, cancer care, and chronic disease management are all included too. You’re even covered for rehab, ambulance transport, and emergency evacuation. It’s a surprisingly comprehensive plan. Perfect for families, long-term travelers, and digital nomads seeking real peace of mind.

SafetyWing Essential

41 with a wife and kid, I’ve highlighted the safetywing complete package. They also have a cheaper one called ‘essential’, which is half the price. CHECK IT OUT HERE, it’s also great (and only $50ish a month).

In fact, I used that for the last 5+ years, until my priorities and responsibilities cranked up with the family! It’s paid monthly at $50ish per month under 40, and $95ish over 40. It covers all travel health insurance stuff. But not cancer, maternity etc for ‘real life’ stuff. It’s built more for travel. Whereas Safetywing Nomad Complete is built for life. Hence why it’s better for me now.

Learn more about the safetynet!

If you’re in a situation like me, or you’re a family that travels. And If you’re interested in coverage like this, check out their site to find out more HERE.

Or if you would like to see prices for your age group/family etc, you can do so here too:

Our Family Travel Plans for the Future

Why do I care about all this? Well for a start, I’M A DAD NOW! I’m also in my 40s, so life is real. It’s not so romantic to be a broke backpacker in mid-life. So although life is still a wild adventure, I also have to be prudent. And this is prudence right now. Also, we have some cool plans, so need to be sorted in advance for health stuff.

So what’s next for us? Pretty much everything. We want Aidan to grow up chasing horizons. In the short term, we’re looking at a campervan trip through Europe while I do a world record thing next summer (watch this space!), possibly some house-sits in Hawaii, and maybe even some time in Georgia or the Caucasus.

Long term? I’d love to give Aidan the kind of education you can’t buy. Well one that money can buy with great schools when we’re in Thailand. But also a different type for a while perhaps too. One built on people, places, and perspective. Maybe worldschooling. Maybe just learning by doing. But definitely not staying put.

We have big dreams and open calendars. As long as we’re moving forward, together, we’re good.

Final Thoughts – The World Is Home When We’re Together

This life we’ve chosen isn’t easy. It takes patience, planning, and a little bit of madness. But it’s ours. And more than anything, it’s real.

We will always have a permanent base in Thailand. But also something more we hope too. Aidan will grow up with friends around the world we hope. And with memories in every continent, and a worldview built on real experience. He’ll know that family isn’t a place. It’s a feeling. It’s something you bring with you, wherever you go.

We’re not done adventuring. In fact, we’re just getting started. And if you ask me what our life plans are?

They’re simple: keep exploring, stay close, and raise our little boy to feel at home in the whole world. Roots in Thailand, and wings ready for the world. And of course, boringly, covered for any emergencies should they arrive. Check out that coverage HERE with Safetywing Complete.