Behind the Scenes of Our Travel Planning

We’ll be honest, choosing our next destination has never been more difficult. We thought that we would have the whole world to explore in our early retirement. But now we’re down to a very small list of countries that will take us.

We’ve received a lot of questions about how we choose our destinations, how we manage visa restrictions, whether cost of living is a factor and lots more. So we’re tackling all the big questions, starting with navigating COVID travel restrictions. And as we go through each one, we’ll give you some clues about which country we’re in right now. 

Travel During COVID

This is the biggest factor in our travel planning right now. Working around COVID restrictions hasn’t been easy, especially since the EU effectively closed its doors to Canadians back in October due to the second wave.  

We actually thought that we would be spending the winter in Portugal but obviously that didn’t work out. And of course, it’s not just a question of which country will let us in. We also need to consider whether we even want to go to a country if the rates are really high.

At this point, we’re only planning our destinations a month or two out. The travel restrictions seem to be in a constant state of flux so we need to be certain before booking any non-refundable flights or Airbnb apartments. We’re currently working with a very small list of countries that we can go to and spending a lot of time watching and waiting to see which ones will open up.

Here’s your first clue as to where we are now: it’s a country in Europe that’s one of the few still letting in Canadians. We’ll provide a few more clues as we go so see if you can guess the country before the end of this post. 

Visa

Once our 30 or 90 days in a country is up, we need to move on. In Europe, this means rotating our time in and out of countries in the Schengen zone. For those who aren’t familiar, a majority of the countries in Europe are part of the zone, which is an area with no passport controls so tourists can travel freely between countries — for up to 90 days. 

If we spend 90 days in Italy or Spain or France then we need to spend the next 90 days in a country that isn’t part of the Schengen, like Croatia or Bulgaria. We’ve just been outside the zone for four months so we were able to come back in. And that’s your next clue: we’re in a Schengen country right now.

Ease of travel

We’re not looking to spend 10 hours on a red eye flight every month. We strongly prefer a short flight or — even better — a train ride to our next destination. 

In fact, that’s part of our travel ethos. We’re trying to see the world slowly which means exploring a region as much as possible before moving onto the next one. So when we left Istanbul, we were very happy that it only took us two and half hours to get to this destination…which is your next clue. 

Weather

One thing we’ve learned about ourselves in this journey so far is that the weather matters. We prefer to be in comfortable climates…not too cold, not too hot and not too rainy. 

This could be the result of growing up in freezing cold Canadian winters or from spending six years living in the steamy tropics.Either way, we’ve found ourselves chasing that sweet spot — warm enough for t-shirts but not too hot. In fact, our current destination is known for being one of the sunniest countries in Europe (and that’s a clue!).

Lifestyle 

We thought when we first set out on this adventure that we would mostly want to spend our time in charming little remote villages. What we’ve learned about ourselves is that those small town experiences are great but when we’re staying for a whole month it’s nice to have some of the buzz of a city, not to mention there are more eating options, more sights and more experiences to enjoy.

But spending time in nature is still really important to us so we try to find a balance. We’re always on the lookout for that perfect mid-sized city that has easy access to big parks and walking trails. Ioannina in northern Greece was perfect for this and so was Split in Croatia. 

We were really excited to come to this location where we are now. Here we’re getting a mix of city life and all the amazing waterfront walking that comes with being an island (clue!).

Cost of living

Because it’s us, you know that we care about the cost of living. We love tracking our expenses and sharing our cost of living series each month.We don’t choose places solely because of the cost. However, if we spend some time in an expensive location, we do like to balance it out with someplace where our dollar goes further.

This particular country has a very high cost of living, comparable to Toronto where we’re from. This possibly comes from being one of the most densely populated countries in the world — and that’s your last clue. 

If you haven’t guessed by now, the country that we’re in is Malta. It’s a beautiful little island of less than half a million people in the middle of the Mediterranean, just a little south of Italy.

Malta has been on our consideration list for some time now because it’s one of the few European countries that’s been open to Canadians during the pandemic. However there is one reason why we were hesitant to come here: the cost of living. Malta is a very expensive place to visit and we’ll tell you more about that in our cost of living summary later this month. 

Despite it being a pricey destination, Malta rates very high for other factors. It was just a short hop away from Turkey; it’s warm and sunny through the winter; and there’s endless waterfront for walking and loads of historic charm. And it’s someplace we’ve never been so it’s always exciting to land somewhere new.