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The ultimate guide

How I Took My Kids Out of School and Moved to a Greek Island for *Three Months*

The (unofficial) guide to a Boundless Life: real costs, logistics, lessons and what nobody tells you

A laughing mum taking a selfie with her two young kids on a sunny Greek island street
Overview · and €400 off
This is an unofficial guide to my experience as a solo worldschooling parent on the Boundless Life program in Syros, Greece, with my 6-year-old son and 4-year-old daughter. I paid full price, so it's a warts-and-all breakdown. If you decide to book, my code gets you €400 off (and gives me a €400 credit if I book again, which, let's be honest, will absolutely be happening).
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Seems that many millennial (heck, all) parents right now are questioning the status quo, because it hasn't worked for us.

School for twelve years. Five years at university. A good corporate job. Repeat every day for 40 years and retire.

They're starting to explore non-traditional schooling options. Homeschooling. Worldschooling. Even 'unschooling' is apparently becoming a thing right now (not even sure exactly what that means). I'm one of the questioners. Here's why.

My little boy is gorgeous. A great learner. Follows the rules. A teacher's dream. And yet, at the ripe old age of six, I could always see the system wearing him down. He'd come home irritated. He'd lash out, overtired and exhausted from trying to hold his little (big) emotions in for six hours a day. Social situations were wonky. And his little light started to dim.

And so, I pulled him out, just for three months, to see whether it would make a difference. Right now, he's attending a worldschool in Greece.

Since sharing that story, I've had hundreds of comments (thanks to a couple of viral posts) from women just like me who are curious about how to make it work for their family. So, here's the ultimate guide to how I made it happen, including:

  • The exact worldschooling program I chose
  • The logistics of uprooting your life, pulling your kids out of school and travelling to another country
  • Real talk, including my expectations v reality
  • The costs involved, and the financial Jenga involved in covering the investment
  • What I do for work, and the different ways other families are making it work for them
  • Things I wish I knew before I booked (and what I would do differently)
  • And more

I will add to this guide over time, so if you have any questions please leave them in the comments and I will answer them as best I can.

Please also remember that this is simply my own experience; I paid full price to attend the Boundless Life worldschooling program in Syros, Greece and my thoughts are my own. Please share with others if you find it useful! I could have paywalled this guide, but wanted to make it free to help as many people as possible because truly, this has been the adventure of a lifetime.

Worldschooling (and the one I chose)

What worldschooling actually means (in plain English)

I had to ask Chatty-G the answer to this one because I still can't quite articulate it myself:

Worldschooling is an educational movement and lifestyle that treats the entire planet as a classroom. Families replace traditional textbooks with experiential travel and cultural immersion, allowing children to learn history, geography and social skills firsthand by engaging directly with different global communities.

And right now, it's having a moment as millennial parents especially start to question the status quo and work becomes more remote.

Boundless Life is probably the best known (and most professionally run) worldschooling option out there right now, and I say that loosely, as someone who is absolutely not ingrained in the worldschooling community and who isn't familiar with every other option out there (so don't come at me!). This is the option I went with, and this guide is based on my own experience as a full-fee-paying participant.

What Boundless Life actually is (and why I chose it over every other option)

I won't lie: the first time I found out about Boundless Life I needed to Google it just to make sure it wasn't a cult. I mean, a group of families all removed from their home country, living together in a different place and having their kids educated remotely (and that logo?). You could forgive me for thinking so.

Turns out it's not a cult. Instead it's quite literally everything I've ever wanted as a mum of two with diehard wanderlust, the ability to work from anywhere, two young kids to wrangle and a penchant for holidays focused on 'pretend living' in new locations instead of ticking off tourist traps.

Pre-kids, I visited fistfuls of countries: young, wild and free. Postpartum and mid-COVID, I started to get the itchiest of feet but couldn't for the life of me figure out how to travel with two little freeloaders in tow.

I gave it a whirl anyway; in 2022 we put our two- and four-year-old on a plane and hauled them across Europe for three months. The result? A lot of special memories, but even more exhaustion, meltdowns, tantrums and hours spent inside in the midday sun while the babies napped. It was less adventure of a lifetime, and more parenting in a different country on hard mode.

Grateful? Yes. Ready to pick up and do it again? Hell no.

Enter Boundless Life. In April, we joined 44 other families on a Greek island called Syros for three months as part of the structured Boundless worldschooling program. Had I been to Syros before? No. Had I even heard of it before stumbling across it? Also no.

The children attend a dedicated world school each day, following the Finnish curriculum. In case you didn't know either (I sure didn't), the Finnish curriculum is widely regarded as one of the best in the world, and is delivered in a way that would be unrecognisable to anyone who went through the Australian or US system.

The students' days are built around quests: learning about the island, doing pottery, theatre games, and working on projects that align with their natural interests. School finishes mid-afternoon and the kids spill out into the village square to play, without screens and without the logistical machinery we'd built up at home just to get our kids socialising.

For the parents, the whole Boundless set-up is equally disorienting in the best possible way. There are events just about every day, and parents connect over coffee and lunches, activities and common values. Nobody needs three months' notice to catch up. And parenting here feels like what people mean when they talk about a village. I hadn't realised how much I was missing that until I found it.

It's pretend living, the ability to get immersed in a culture, children who settle and make friends, and everything I wanted my first three-month European adventure to be.

Boundless Life: Syros, Greece and other locations

Boundless Life operates in a heap of different locations across Europe, Asia and South America, and from what I hear, there are more on the table too. In addition to Syros, there's (in order of the ones I want to do):

  • La Barra (Uruguay)
  • Sintra (Portugal), although I hear this location may be moving to Cascais, which is the one I most want to do!
  • Estepona (Spain)
  • Kamakura (Japan)
  • Kotor (Montenegro)
  • Pistoia/Tuscany (Italy)
  • …and I hear Annecy, France is on the horizon, too

From what I can see, most families pick their first location based on personal preference. Once they're in the program though, community becomes another huge factor, with families often choosing subsequent locations based on where their friends (and their kids' friends) are travelling to next.

Things I wish I'd known before booking

True to form (anyone who knows me knows I generally make wild, last-minute decisions), I booked our Boundless Life experience just six weeks out from the start date.

I found out about Boundless Life in March, and it was an immediate yes in my bones. I knew I would make it work, and due to some difficult life circumstances I wanted it to be sooner rather than later. I signed up for an information session and the next day was on a call with a family rep. By the end of the call, I knew I wanted to go to Syros. The only hitch? It was sold out for the next three cohorts.

So, I did what any non-rational person would do: my very non-woo-woo self sent a little signal to the universe that if it was meant to be, a spot would come up. A few days later, the family rep called. A new house had been added to the Syros inventory, and I was in if I wanted it, for April, about six weeks out. I was an immediate yes.

"Was it the right decision for us? Ab-so-freaking-lutely."

At the same time, there are a few things I wish I'd known ahead of time:

Cohort size matters. Our Syros cohort was big: 44 families, many travelling from other Boundless locations. If I were booking for the first time again, I'd intentionally choose a smaller location or cohort, and make sure there were other first-timers there too. Figuring out the social side was tough on both me and the kids in the first month. With that said, Syros in spring and summer is magic, so if you asked whether I'd have picked somewhere else, my answer would be no.

Location matters. It's only once you're in the program that you get to chat to others about their real-life experience of each location. We lucked out with Syros, an alumni favourite. I'd research and ask alumni about each location before booking your first.

Pricing varies a lot. Pricing is supply-and-demand based, depending on the time of year and the popularity of the location. Syros from April to June has huge demand and sits on the priciest side. Visiting in January would be a huge saving.

Logistics

My personal roadmap: how I made it happen in 90 days

First things first: I don't recommend doing Boundless last minute like I did. Spots sell out way in advance these days, and booking last minute makes the logistics harder. But of course, I did book last minute, so here's what the steps looked like for me, in case stepping it out like this helps you see how it might be possible for you, too.

Step one

Ask the school for permission to miss a term

My son attends a private school on the Gold Coast, and there's a waitlist to get in. I called the enrolment officer to ask. What was at first a cautious 'no, we would not hold his place' turned into an enthusiastic yes after I was asked to put the request in writing for the principal. Here's what I wrote, in case it helps your case also:

Steal my email

Hi [Name],

Thanks for your call. As I mentioned, I would like to find out the possibility of doing a three-month cohort this year with my children overseas. Here is a brochure and more info on the education provider; the location is TBA (they have branches in Spain, Japan, Greece, Uruguay, Portugal etc).

It would mean taking [my son] for a full school term, but I do believe he would benefit from the experience so much. I am unsure on their availability, but it would be either term 2, 3 or 4.

I am writing to find out what is possible. My preference would be that he stay enrolled, but I understand that this likely isn't possible, so what we do will depend on making sure the school is happy and he can continue on afterward. Let me know the next steps.

Thank you so much,
Stevie

In the end, we were required to pay his tuition for the term and submit an application for exemption from school to the principal. This is a requirement in the Australian state I live in. My understanding is that the principal can approve this if it's under a certain number of days, and he did!

Step two

Speak to my daughter's daycare to save her spot

My daughter attends the daycare attached to the school, which also has a long waitlist. I spoke to the head of the centre, who said approval would be required. Here's the formal request I sent:

Steal my email

Hello [Names],

I'm writing to follow up on our brief conversation this morning and put my request in writing. I'm exploring the possibility of taking my children overseas (most likely Syros, Greece) for Term 2 as part of a three-month educational program run by a company called Boundless. They have a late place available in their April cohort, which runs from April 4 to June 30.

I'd love to understand what options might be available, as I absolutely don't want to jeopardise her place upon return; she is incredibly happy there. I wouldn't go if she wasn't able to return to her place when we come back.

I completely understand that you need to consider enrolment continuity and staffing, so I'm wondering what arrangements might be possible, for example whether another family might take some or all of her days during this period.

It feels like Jenga trying to get all of the pieces to fit together, but I know what an incredible opportunity this would be for our family, so I'm grateful for you considering.

Thanks so much,
Stevie Dillon

In the end, the daycare was okay with holding her place as long as we paid fees, but there was one big hitch: government funding is cut in my state if you're overseas for more than six weeks, so holding her place would mean paying full fees for a time, unless I dropped days or another family took her place for those dates. Fortunately, another family took three of her five days while we were away, I dropped Fridays altogether, and some families took the remaining days on an ad hoc basis.

Step three

Book with Boundless Life

Midway through steps one and two, I was told I needed to make a final decision. I took the place and paid up front, hoping the rest would work itself out. It did, but it was a risk: a case of jumping and hoping the parachute would appear. I have a tendency to do that, and it has a tendency of working out.

Step four

Book flights

Flights were booked (using points), we packed a couple of suitcases and we were ready to go. Accommodation, transfers, schooling and everything else were managed by Boundless, so logistically it really was a turnkey solution.

Step five

Visas

As an Australian family, we attended our three-month cohort on the short-stay Schengen visa, which allows visa-free travel in the Schengen Zone for three months in any 180-day period. Because I run a remote business and would be working (lightly, in the end), I called the Greek Embassy in Australia to check this was permissible. They confirmed it would be okay, so long as my time in the country was under 90 days. Other participants staying longer applied for a Digital Nomad visa.

Step six

Rent out our home

To help fund the trip, I rented out our home for three months. New tenants signed a lease just a few days out, so it required a lot of last-minute packing!

Step seven

Pack, and leave

My proudest life achievement to date was fitting both cold- and warm-weather wardrobes for myself and two children for three months into one big suitcase and two carry-ons. This turned out to be very, very important, because it's impossible to carry any more than that as a solo mum with two young kids.

If I had my time again, I'd pack even lighter: one mid-size suitcase, and I'd ditch the kids' backpacks (or make them much smaller). The only time I really felt stressed was packing and unpacking our haul during ten days in London at the start of the trip. You can always pack more lightly than you think. So much can be bought when you arrive, and you likely don't need as much as you think (toys especially).

Money, costs and financial Jenga

How I made it work financially

The truth is, worldschooling (and Boundless Life in particular) isn't cheap, and it's a privilege to be in a season of life where it's both financially and logistically possible. For us, it worked for two reasons:

  • I run an online business and can work remotely, though it was really in 'maintenance mode' while we were away, because it's hard to focus when surrounded by fun on a Greek island.
  • I own a home, and was able to rent it out while we were away, which provided some income.

For other families we met along the way, it looked a little different:

Remote workers

Working remotely for companies overseas.

Remote businesses

Running businesses online from anywhere.

Savers or sold up

Selling assets at home to fund a season of travel.

Early retirees

FIRE families living off passive investments.

Pensions

Retired military or police using a pension to travel.

In our Syros group it really was a mix of all of the above. Some families didn't work at all. Most had one parent working at least some of the time. And then there were solo parents like me: I worked part time; another solo mum worked full time. Luckily, every Boundless location comes with a co-working hub, and the view from ours was pretty spectacular.

What it actually cost us (full breakdown)

Keep a couple of things in mind. One: we booked the spring Syros cohort, probably the most 'expensive' one, as demand is high for a warm-season Greek island. There are many less pricey locations and seasons, and Boundless has a calculator on its website. Two: Boundless prices in euro, which pushes the price up for Australians (and Americans).

The real numbers

Boundless Life

Accommodation, three-bedroom home (less €1,800 bundling discount)€15,114
Community fee (one adult)€1,800
Education registration (two children)€800
Education fee, child one€6,900
Education fee, child two (less 10%)€6,210
Subtotal€30,824

Optional extras

Family cooking experience€146.50
After-school pottery, two kids, ten weeks€430
After-school theatre games, two kids, ten weeks€288
Parents' boat trip€93
Farm morning with horse riding€123
Greek plate-smashing night (plus kids' movie night)€112
Family boat trip and BBQ€275
Subtotal€1,467
Grand total€32,291
≈ AUD $52,000 ≈ USD $37,000 at June 2026 exchange rates

I get that this might cause sticker shock. It did for me when I first saw the price. But context is important: how much would a three-month trip to Europe with your family cost you? How much is rent? Schooling? Activities? When I calculated our family's annual spend with education, housing and bills included, it came to about $40,000 AUD a quarter, so the cost is actually comparable to living at home.

On top of these core costs were day-to-day living expenses (mostly food and drinks), a weekend in Santorini, a weekend in Paros, a mums' night in Mykonos and a mid-cohort break to London. Otherwise, our days were spent at beaches or the square, both of which were free.

Juggling work and Boundless (aka Boundless is a full-time job in itself)

Whilst you can work during Boundless Life, there's usually so much going on with activities and social gatherings that it can feel like a full-time job! If you suffer from intense bouts of FOMO like I do, it can be challenging to juggle both. Sustaining my business? Fine. But mustering the time, energy and space to grow it was something I decided to forgo about two or three weeks in. A few reasons:

Greek island life. Three months is a 'long' time, but it passes in the blink of an eye. Working at my usual pace would have meant missing the things that make this special: slowing down, forming connections fast and soaking up the moments.

A packed activity schedule. Every single day there's at least one activity for parents: a Boundless circle, a learning experience, a farm visit or boat trip, a walking tour. You realise a couple of weeks in that you just can't do everything.

Solo mum life and big emotions. Moving to a new place, making friends and adjusting to a new normal took more time than I expected. Regulating my own emotions and two little people's took more energy than I'd anticipated, especially at the start and the end.

Are these champagne problems? Sure. But they're worth being mindful of if you intend to (or need to) work full time while 'doing Boundless.'

What I do for work

I'm an ex-lawyer who started an online business called Lifestyle Business School around ten years ago. I create content on the internet and sell digital products. Remote work like this is perfectly suited to worldschooling, because it can be done from anywhere. Do I recommend it? Sure, it's changed my life. Is it easy and quick? No.

The reality (the bit Instagram doesn't show you)

Pulling your kids out to do something different is often held up as the 'happily ever after,' when actually it's really just the start of a whole new adventure: imperfect, full of bumps, and maybe a little different to the reality sold online. Here's our experience, expectation v reality style.

Social dynamics

Expectation

A brand new, fresh social start and the opportunity to make new friends from scratch.

Reality

Many families had already been to previous world schools and the kids knew each other. We all played social Jenga, and my kids really were the new kids at school.

Regulated kids

Expectation

Calm, regulated children thanks to a more play-based curriculum.

Reality

The change was big, and so were the emotions. So much 'new' to process, and lots of support needed from me.

Friendships

Expectation

Easy friendships, international pals and no complex social dynamics.

Reality

My little boy took time to adjust. Seems your problems don't disappear when you jump on a plane. Go figure!

Life outside school

Expectation

Fun! Excursions! Beach trips and play dates galore.

Reality

A huge wave of sickness in the first week or two, and much more kid downtime than usual as they adjusted.

Worldschooling, for us, wasn't so much a picture-perfect fairytale solution as an opportunity to step out of the rigidity of our schooling schedule at home and try something new. Actually, it taught us all resilience, up-levelled our social (and my parenting) skills and required us to adapt, skills that will serve us when we return home, too.

My son (6) didn't always want to go into the classroom; he's quiet, and our class had 16+ students, most with big personalities. He eventually found his person, and that was a big turning point. My daughter (4) found the big days tiring, so I kept her home some days for a break. She mostly had a great time.

What our days actually looked like

7.30amWake a little later thanks to European bedtimes, breakfast and get ready for school.
8.15amWalk up the many stairs to school, counting cats on the way and chatting to other families.
8.45amDrop-off. Teachers welcome the kids, who swap outside shoes for slippers.
9amCoffee, sitting down. I learned quickly that takeaway isn't the Greek island way.
10amFocus work at the co-working hub, three mornings a week.
12pmA gyros for lunch, or one of the many cafés.
1pmA Boundless circle or learning event at the lounge.
3pmSchool pick-up, walking up the stairs with the other parents.
4pmThe square: hours of play for the kids while parents chat nearby. Everyone's favourite part.
7pmDinner on the rooftop, then bath and bed by 9.

On weekends we'd wake later, then head to the beach, hang out with other families, or catch a ferry to another island for an adventure.

The highs (in no particular order)

Community. Most families join for the education, but they stay for the community. I've travelled for three months without it and with it, and the latter was 100 times richer.

Fun. Boundless made me realise how much I'd forgotten to prioritise fun. My mission now? To take some of that home with me.

A chance to reset. Many families come to Boundless at a turning point: a sold business, burnout, or a quiet sense that something needs to change. Some of the most beautiful conversations were with other mums in a similar season.

Connections. Nobody leads with what they do. Instead, you get to know people who share an ethos of really living, often in spite of (or because of) big life circumstances.

Living, not visiting. Three months gives you time to really experience a place, and Boundless gives you the connections to do it properly.

Spontaneous socialising. At home, catching up needs a three-month lead time. Here, it happened most afternoons.

The lows (also real)

I want to be clear: 80% of this experience has been pinch-me incredible. Truly. And also? It wasn't perfect. Nothing ever is.

Housing. Going from a big family home to a small apartment was an… adjustment. If you can choose, look for the vibe, location and natural light you want, especially with young kids.

Internet. Spotty at best in our accommodation, so calls happened at the co-working hub. Check this before booking if it matters to you.

Kid issues. My kids struggled socially at first, and most days were a slog to get them into the classroom, even once things settled.

Orientation. With so many families already knowing each other, the first few weeks were exhausting. I think Boundless could do more to connect newbies early on.

Costs. Accommodation especially is pricey. You're paying for a turnkey solution, and there are other options, but I do think you get what you pay for.

Does the reality match the expectation?

Here's the truth: this experience transformed all of us, but not necessarily in the way I'd expected. The (perhaps rose-tinted) hope was that a world school would 'solve' the issues we'd had at home. The reality? Worldschooling has been the start of a new chapter, not a picture-perfect fairytale.

Changing your environment doesn't mean everything magically settles. The same challenges follow you; they just show up somewhere new. And then there was me. I expected to arrive and instantly relax into the slower Greek way of living. That's been the unexpected part: learning how to actually be in a life that isn't rushed. To sit down and drink my coffee. To prioritise time with new friends instead of measuring my days by how much I produced. To focus on being, instead of always doing.

Would we do it again?

A heart-stopping, resounding yes.

The biggest gifts so far? More resilience. More confidence. More softening into a version of life that doesn't require or reward rushing, to-do lists or how much you can get done in a day.

"Once you've experienced a different way of living, it's hard to unsee… and even harder to go back."

Personally, I think a year back to back would be tiring. I love the idea of doing one Boundless cohort a year, in the spring: three months of life elsewhere, without giving up life at home. For now, we're letting this experience shape how we live back home (but don't be surprised if you see us on another plane very soon).

FAQs and resources

Where are people from?

Most families in our cohort were from the USA. There were two Australian families (us and one other), one from the UK, and a couple of half South American families.

Are there many single parents?

I did Boundless solo! Two other mums did too, and two more only had their partners with them for a week or two. Doing it solo gave me a village; I never felt alone.

Got another question?

Add it in the comments and I'll answer honestly.
Thinking of booking? Get €400 off.
I paid full price for my Boundless Life experience, so this is an honest account. If it helped and you decide to book, use my code for €400 off (and I'll get a €400 credit if I book again: win-win!).
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Written by Stevie Dillon

questions? leave them in the comments, I'll answer every one

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