Our Never-Ending Search for the Perfect Winter Escape

And where we’re headed in 2026

When we decided to base ourselves back in Canada, we knew that the coldest, darkest months of the year would most certainly be spent elsewhere. After all, our little corner of Ontario is lovingly known as the “snow belt” and for good reason. We were greeted in early November with more than a foot of snow — enough to pop on our cross-country skis and do a loop around the nearest field. Our village goes into hibernation mode as the winter settles in and we’re very fortunate if we see at least one other human being when we walk our dogs around town.

Just another day in the snow belt

Past winter misfires

But where to slow travel for a few months in the winter isn’t the easiest dilemma to solve, especially if you’re hunting for brand-new destinations with decent weather and lots of outdoor adventures. During our first few years of nomad living, we never managed to plan winter properly. In the first year of living out of our suitcases, we spent the coldest, darkest months of winter first in Fethye, Türkiye and then in Florence, Italy. Both cities require a down coat and a sturdy umbrella during the off-season.

In between downpours in Florence

The next winter we faced global COVID lockdowns and found ourselves back in Türkiye and then Malta, both picked from the very small list of countries that were accepting Canadian passports at the time. This is when we learned (for the second time) that apartments in Mediterranean countries generally aren’t winterized. New purchases that season included slippers for the ice-cold tiles in our drafty Airbnb in Sliema, Malta.

Year three we were in chilly Spain and — wait for it — Türkiye yet again. There had been another round of COVID lockdowns and Turkiye was, as usual, our fallback plan. This time we were hit with a wildly unseasonable cold front in the city of Izmir and found ourselves scurrying to tourist attractions wearing as many layers as possible.

Very underdressed for the weather in Izmir

By our fourth winter of full-time travel, we realized that perhaps a new continent was in order and happily explored Colombia, with the Coffee Region, beach-town Palomino and mountain-village Minca being particular favourites. Year five saw us on the balmy island of Madeira, where we were won over by Funchal’s historic downtown with its spectacular mountainous backdrop.

Basking in the winter sun on Funchal’s cable car

Our (very specific) wish list

Now that we’ve settled back in a northern country, the question of where to go for the winter is even more important. And selecting just the right place is increasingly difficult as we become more experienced travelers and our wish list for destinations keeps growing.

Here’s a small sampler of criteria from the brainstorm for our upcoming winter getaway: must be a new-to-us destination; great weather; great food; a decent gym nearby; easy access to nature for hiking; and clean, stylish Airbnbs available that are also pet-friendly (because naturally our two dogs, Jasper and Huxley, will be joining).

Very important, there must be enough varied experiences and attractions available that the destination merits a three-month stay. That last one is critical because our appetite for novelty is such that we aren’t content to stay in just one apartment in one city for an entire three months.

And the winner for 2026 is…

We weighed many options for the winter of 2026, including such wildly different countries as Taiwan, Argentina, South Africa, and Cyprus. After a decision-making process that made extensive use of a spreadsheet, weather forecasting websites, and a scoring system (yup, we’re nerds at heart), we finally landed on what will be our home-away-from-home this winter: the Canary Islands.

Although we’ve been to mainland Spain before, we felt that the Canary Islands are distinct enough to constitute a new destination, albeit with a familiar Spanish flavour. We’re looking forward to spending three months hopping from island to island and hike to hike.

We’ll start in Gran Canaria; make our way to Santa Cruz de Tenerife; pop over to La Gomera for a week of vanlife; and then circle back for a long stay in one of Tenerife’s more authentic neighbourhoods, far from the touristy resorts of the South Coast. We’re looking forward to sunshine, patio dining and long walks on the waterfront while Canada is blanketed in yet another layer of snow.

If you’ve been to the Canaries, please do send your best travel tips and favourite restaurants our way. And if you’ve got your winter getaway all lined up, we’d love to hear where you’re going.

In the meantime, we’ll be busy shovelling the drive and counting down the days until our next adventure.

See you on the road,

Stephanie & Gillian