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Moving to Portugal

We’re moving to Portugal.

I feel like I’ve been keeping this secret and holding my breath for way to long…

It’s official, we’re moving to Portugal in just under 5 months.  We’ve already booked our red eye flight for August 28th, 2023 and will be arriving exactly 1 week before school starts for the kids.

We will be living in the magical (and also touristy) town of Sintra for the first 3 months.  It seems to be the castle capital of Portugal and along with it’s cobblestone streets, feels like it’s right out of a fairytale.  

As you can see in the image above, most of the buildings are also decorated in brightly colored stucco that only adds to the charm.

There are also a total of 5 castles in Sintra that will all be within mostly walking distance to us.

Below is a picture of the famous Pena Palace which is of course stunning, and has been named a UNESCO World Heritage Site.

Moving to Portugal - Pena Palace

We visited this castle on our first trip to Europe (including Portugal) back in 2014 on a day trip from Lisbon to Sintra and Cascais.

Keep reading below to find out all the details of why, where, how and what our big plan is for our family going forward.

Why we're moving to Portugal.

As you can imagine, that’s a pretty loaded question, that has a ton of answers.

The first reason has everything to do with climate.  Average temperatures typically don’t go below 10 degrees Celsius (50 Fahrenheit) and 25 degrees Celsius (80 Farenheit) in South Central Portugal.

That’s a far cry from the cold temperatures (and winters) we currently experience in Ontario, Canada.  With only about 3 total months of “summer weather”, we’re looking for something different.  We can’t wait to be able to comfortably spend 365 days a year outdoors.

The next reason we chose Portugal specifically, is that Scott’s family, is originally from Portugal, so we have ties.  Although there really aren’t any family members still in Portugal, both of his parents we’re born on the island of Sao Miguel, in the Azores.

Scott mostly understands the language and it will be amazing for the boys to learn more about their ancestral roots and learn to speak the language.

The boys have also started learning simple words and phrases using the Duolingo app we’ve downloaded on their Ipads.  It’s a free app where they can start to learn and it’s freaking adorable to hear them repeating words.

The third reason is ofcourse the food and the slower pace of life.  We’ve grown a little tired of the constant rat race and feeling like there isn’t enough time as a family.  Portugal is one of the most beautiful, family friendly places we’ve visited and the food was beyond delicious.

Below is a picture taken on a street in Lisbon during our 2022 Portugal vacation last summer with the kids. 

moving to portugal | street in lisbon

Not only is the food fresher and prepared with better grown ingredients, it even costs less overall than it does here.  Grocery shopping at local markets is also cheaper and you know that you’re consuming way less pesticides and additives than you are in North America.

In terms of the culture, there is soo much history to visit and learn about – but I also mean the European culture in terms of the way everything seems to built around family.  Young, old and everything in between always seem to be gathered together, there is such a focus on the “family experience”.

Next up, I’ll walk you through how we’re actually making this all happen.

How we're moving to Portugal.

I am 100% a believer in the universe showing up for you and giving you the things you need, even when you don’t know it yet.

Through one of the “Expats in Portugal” Facebook Groups I joined, I randomly found a link in one of the threads to a company called Boundless Life.

While at first I didn’t think it was what we needed, I quickly realized the massive benefit it would give us as a family to travel and experience a new Country – without all of the stress that comes along with relocation.

Boundless life is a company that was founded specifically for Digital Nomad families that would allow them to easily travel and experience other cultures.

They currently have 4 locations – Sintra, Portugal – Syros, Greece – Tuscany, Italy – and Sanur, Thailand (which opens July 2023).

The idea is that you can do 3 month intervals and at any of their locations and they provide the lodging fit for your family, the private school for the kids and the co-working space for the parents to work from.

Most countries allow you to travel within them for up to 90-days on just a tourist Visa which is why the school cohorts are 88-days long.  So you can simply show up and limit the amount of paperwork you need to worry about before hand.

The private school is inspired by the world-renowned Finnish system and all locations follow the same curriculum so you can travel without your kids missing a beat or falling behind.

The residences are also full-furnished and they will equip you based on the number of bedrooms you need and any additional baby/kid needs like cribs, high chairs etc…  It also includes all of your utilities and internet connection to further eliminate any stress of trying to set that up.

As a Boundless family – you also have access to a coworking hub so that you can still have your privacy and a quiet space to work while the kids are at school.

Below is a picture of the coworking hub in Sintra, Portugal that we’ve borrowed from the Boundless website.

Although I’m typically a lover of working from home, I can’t wait to also experience working in this incredible space on a regular basis.

Now we plan on actually staying in Sintra, Portugal for the three full cohorts (school semesters), but I think that there is a chance we might end up in Italy or Greece for one of them instead.

The kids education

As I mentioned above, the private school system is based on the world-renowned Finnish school system.

The cohorts (semesters) are from September to end of November, January to end of March and April to end of June.

That means we will be able to travel back home to Canada for the month of December to spend Christmas here with family.  I won’t be looking forward to the cold, but the snow will likely be a nice touch.

Boundless also offers summer cohorts to visit their destinations where the kids get to keep learning in a fun environment (while you get to work) and you all get to travel and experience a new place.

One of the biggest factors that made us decide this was the right fit for the kids was the way they break up the school day and the school week.

We’ve pulled these images from the boundless website so you can get a glimpse:

One of my favorite parts of the day here is the connection time.  After going through my certification as a Mindset Coach, I feel like connection time and a moment to center themselves is a necessity for kids these days.

I also love the cultural immersion time where kids have the opportunity to really deep dive and learn more about the local culture.  The kids will also have the chance to further learn Portuguese right at school.

And lastly is the Boundless time, where kids get to expand and learn deeper on a subject they are interested in and most passionate about.  Instead of always telling them what they need to learn, this gives them a chance to explore their unique interests, right in school.

Also worth mentioning is that the kids will have nutritious lunches prepared at school for them.  That’s a massive blessing for me and no more having to make lunches in the morning!  If you know, you know.

Affording full-time travel

Because we still be considered Canadian residents and will be coming home in the month of December, being with Boundless means we’re travelling as oppose to relocating.

I will get to run both of my online businesses, Lady Boss Studio and Funnel Breezy and Scott will be able to keep helping to run his physical business from a limited online capacity.

While this isn’t a massive change of scenery for me, I know it’s something that Scott never imagined would be possible or that he even necessarily would have wanted in the past.

And the most beautiful part of this is that we don’t have to commit.  We get to simply treat this as an incredible experience that has no pressure or stress to move any of our stuff, buy into real estate or move either of my companies.

We also sold our house a while back and have chosen some dividend investments that will contribute to our monthly earnings as an extra bonus.

Most online entrepreneurs start their business because they are chasing after both time and financial freedom, and I feel like I’m really putting my money where my mouth is on this one.

Never in a million years did I think that would mean travelling full-time with my family, but it has really turned out to be exactly what we want.

I didn’t get on my first plane until I was about 21 years old.  Growing up with a single mom meant our big summer vacations were camping at a local provincial park.  And I’m not knocking that, most of my favorite childhood memories come from those summers.

And while we will still be camping for a few days this summer with the kids at that exact same campground, I’m excited to be able to show them other parts of the world.

Sj is lucky enough to have been on three vacations so far (Jamaica, Florida and Portugal) and Karden has been on two (Florida and Portugal).

Here is a picture of the boys on our Florida vacation last spring, soaking up their time at the beach.

Moving to Portgual - the kids in Florida

What's next after Portugal?

Well, our original plan was to do the boundless experience in just Sintra for 9 months to really give us a feel for what it would be like living there without the pressure.

Then we kind of dropped the ball and didn’t apply for our Digital Nomad Visa earlier enough.  Apparently 5 months in advance was not soon enough to get us an appointment at the Toronto Consulate.

But like I said before, I think sometimes the universe gives you what you need, instead of what you think you want.

So we will still be going to Portugal from September to end of November and then we will be back as planned in Canada for December.

Then we’ve made the HUGE decision to travel to Bali, Indonesia for the following 3-month cohort from January to end of March.

This will be utterly and completely out of our comfort zone, but realistically, that’s the whole point.

It’s one thing to travel and stay some where you’ve already been twice and feel pretty comfortable, but it’s another to really experience something entirely new.

And I’m ridiculously excited.

The plan will be to come home at the end of March and finish the Visa Application process and then officially move to Portugal by June of 2024.

You’ll have to stick with us to find out if we stick to the plan or if the travel bug really hits and we decide to spend another year in various other Boundless locations.

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Tasha DaCosta
Tasha DaCosta

Founder and CEO of Lady Boss Studio and Funnel Breezy and also proud Mama and wife who travelling the world and creating incredible memories with her family.

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