Working holiday in Canada: first winter in Montreal
The first thing Montreal does, when you land in January with a one-way ticket and a working-holiday permit, is tell you the truth about cold. Not the cold of a ski weekend — the other one, the structural kind, where the air bites the inside of your nose and the snow squeaks under your boots like polystyrene. I stepped out of Montréal-Trudeau, my French winter coat suddenly revealed as a light jacket, and laughed, because there was genuinely nothing else to do.
A working holiday is a strange kind of trip: too long to be a holiday, too temporary to be a move. You arrive with a backpack and a plan that fits on a napkin — find a room, find a job, survive the winter — and almost all of it, in the first week, happens through a phone. Which is exactly the part nobody warns you about.
The first cold, the first week
Canada is famous for two things in winter: the beauty of it, and the price of its phone plans. The first is free. The second is not — local mobile is genuinely expensive, and the good deals usually want a local address and a credit history you don't have yet. So my first days ran on an eSIM I'd installed before leaving: enough to land connected, open a bank account, message three landlords from a freezing bus stop and keep my family in France reassured while I figured out the rest. It was never meant to replace a Canadian line for a whole stay — just to carry me over the gap until I could open one properly.
« A working holiday isn't a trip you take. It's a winter you move into. »
That gap is where everything important happens. Apartment hunting in Montreal runs on Marketplace and Kijiji, on visits booked by message and confirmed an hour before, on maps that have to work while you stand on an unfamiliar corner in the dark at 4:30 p.m. — because in January, that's already night. Being reachable wasn't a comfort. It was the difference between a viewing and a missed viewing, between the right metro exit and twenty extra minutes in minus twenty.
The city under the city
Then someone showed me the secret that makes a Montreal winter not just survivable but oddly cozy: the underground city. Tens of kilometres of connected passages stitch together metro stations, malls, food courts and office towers, so you can cross a frozen downtown in a t-shirt if you plan your route. I spent a lot of January learning those tunnels, coffee in hand, phone guiding me through a labyrinth that the snow above never sees. Above ground, the plateau's spiral staircases wore white; below, the city hummed along, warm and lit.
📶 Hugo's tip
For a working holiday, think in two stages: an eSIM for the arrival — so you're connected from the airport for the bank, the apartment hunt and your family back home — then a local plan once you have an address, for the long haul. Download offline maps of your neighbourhood and metro before you land; January darkness comes early and you'll navigate in it. Check your phone's compatibility in 30 seconds here and find your Canada plan for the first days on the destinations page.
What I take away
By March, the cold had stopped being an event and become a texture — just the weather, the way rain is the weather in France. I had a room, a job, a favourite tunnel and a phone bill in two currencies during the changeover month. A working holiday teaches you how much of settling somewhere is just logistics, and how much lighter the logistics feel when, for the first scary week, you can simply reach everyone you need to. The winter you can't outsmart. The connection, you can sort out before you land.
— Hugo, from a heated tunnel under downtown Montreal.