The flight to Toronto was smooth, but our first 24 hours were anything but.
I’d tried to set up mobile service from Chicago so that when we landed, our phones would just work. They didn’t. We spent our first stretch at Toronto’s Pearson International Airport hunting for WiFi so we could reach Lucky Mobile and figure out what had gone wrong. After a lot of bouncing between support agents, we learned that despite Lucky telling us everything was set up correctly before we left Chicago, our credit card had actually declined the transaction — so our plans had never activated in the first place.
We decided to head to our Airbnb and sort out the phone situation from somewhere more comfortable, only to realize on arrival that we needed working data to follow the check-in instructions and get into the Airbnb itself. Julie remembered the gist of it — go through the side gate to the back of the building, then find a key in a lockbox — but we still needed the actual code.
Fortunately, another guest staying on the main floor heard our predicament and let us use the building’s WiFi. We got the code, opened the lockbox, and were finally in.
I got straight on the phone with Lucky Mobile while Julie explored our new digs for the next month. Between the original setup attempt in Chicago, the airport detour, and now another hour on the phone from the apartment — plus a tense twenty minutes convincing Capital One to actually let the charges through — our phones finally had Canadian numbers and a working data plan.
That’s when Julie filled me in on what she’d found. The floorboards were warped and lifting throughout the unit, from the kitchen to the bathroom, with sharp edges that were genuinely dangerous to walk on barefoot.
It was also freezing. We’d booked a garden apartment that looked lovely in the photos, but there was no thermostat in our unit — the blower for the entire building lived in our apartment, and it was loud.
And then there was the bug Julie spotted in one of the bedrooms, which vanished under the trim the moment she turned on the light. No photo — sorry.
While I was still on hold with Lucky Mobile, Julie reached our host and laid it all out. He explained that the thermostat lived on the main floor, that the AC would likely run constantly given how hot Toronto was, and that he could bring over space heaters if needed — or we could just use the decorative fireplace. The floorboards, it turned out, had warped after a water issue with a previous tenant that couldn’t be fixed while the unit was booked. He asked for a photo of the bug so he could arrange to have it sprayed.
We called Airbnb and explained that the place we’d committed to for a month wasn’t going to work. After we documented everything, they told us they’d probably be able to help — but in the meantime, Julie and I decided to get dinner and find a hotel for the night instead.
Julie found what looked like the perfect place on Hotels.com, and we booked two nights. When our Uber dropped us off, though, it didn’t look anything like a hotel. She double-checked the name; I checked Google Maps. The real address was a couple of blocks away.
So we — mostly me — started rolling four suitcases, carry-ons balanced on top, down the street. It was close to midnight and still in the 80s. We were sweating, stressed, and increasingly unsure this night was ever going to end. When we reached the address, there was no hotel there either. Julie pulled up the confirmation email: the address listed was actually the first place our Uber driver had taken us — an apartment building.
We called the number on the booking. It turned out this wasn’t a hotel at all — it was a short-term rental, and yes, also technically an Airbnb on the back end. We were told we needed to pay a non-refundable $50 damage fee and agree to a set of terms via a link before we’d get check-in instructions for an apartment inside the building.
We walked back, found the building’s security concierge, paid the fee, and got our instructions: there was a room off the lobby with a lockbox, and I now had the code. I walked in, tired but hopeful, and found over fifty identical lockboxes crammed into that tiny room. Reading glasses on, phone flashlight out, I started searching. A few minutes later the concierge — genuinely a great guy — came in to help, and together we finally found ours.
The apartment itself was small but clean, with great views. In the morning, Airbnb support let us know they were releasing us from our original month-long booking, and we were free to find another place.
Missteps and detours, right from the very first night.
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