Travel Day: How Not to Start Your Dream Trip to Madeira

Miscalculating My Flight Like a True Travel Pro

Well, to say I was confused is an understatement. My flight to Madeira was at 12:30 AM on September 21st, so naturally, in my brain, I needed a ride to the airport on September 21st. Makes sense, right? WRONG.

A full week before departure, I woke up in a panic thinking, “Wait… when do I actually leave?” If my flight is at 12:30 AM, then technically, I need to be at the airport the night before. So now I’m scrambling to re-coordinate my ride like the seasoned traveler I (clearly) am.

Sciatica: The Uninvited Travel Buddy

Just when I thought my biggest problem was airport logistics, my body was like, Hold my beer. A week and a half before my trip, I got hit with the worst sciatica flare-up of my life. I mean, I could barely walk, which is super convenient when you’ve planned an epic hiking trip across Madeira.

The crown jewel of my itinerary? The Pico do Arieiro to Pico Ruivo hike—one of the most intense and scenic treks in Portugal. But as my departure date crept closer, reality set in: I wasn’t going to be hiking anything. In fact, I’d be lucky if I could hobble around without looking like I just escaped from an old folks’ home.

Cue desperate last-minute treatments: acupuncture, chiropractic adjustments, an Aches Away IV drip—you name it, I tried it. Things were improving slightly, but two days before my flight, I still couldn’t walk more than five minutes without soul-crushing pain.

I debated canceling the trip altogether, but I’d been hyping this up since January, and honestly? I was too stubborn to back out. So I sucked it up, accepted that my trip would look a little different than planned, and braced myself for whatever was coming.

Flying High—Literally

Travel day was a blur, mostly because I stayed completely doped up on painkillers. I arrived at the airport high as a kite, but at least I made it. No canceled flights, no delays—small victories.

My Itinerary:

  • 12:30 AM – Depart Calgary (yes, I will use 24-hour time even though I hate it because airlines insist on it)

  • 6:30 AM – Land in Toronto

  • 11:15 AM – Fly to Madeira

  • 11:15 PM – Arrive in Funchal

Not bad, right? Smooth flying, except for the whole my body is betraying me thing.

The Hostel Keycard Fiasco

I had booked a hostel in Funchal, and on the day I left, they casually mentioned, “Oh, by the way, reception closes at 4:00 PM.”

Ummm. Excuse me?

So now I’m envisioning spending my first night in Madeira curled up on a park bench, which would already be less than ideal, but add excruciating back pain to the mix, and I might as well just call it quits. Thankfully, after some panicked messaging, they agreed to leave my key in a lockbox at the front door. Crisis (sort of) averted.

I arrive in Funchal, clear customs in record time (bless small airports), grab a cab, and head to my hostel. Since it’s Saturday night, I assume people will be up drinking, partying, and making noise. Perfect. I won’t be an inconvenience if I arrive late.

I was so wrong.

I walk in to complete and utter darkness. No lights, no sounds, no sign of life. I fumble around, blindly searching for my room, tripping over things and trying not to wake anyone up. This place is old as hell, so every single step sends groans and creaks echoing through the walls. I finally find my bunk and collapse, ignoring my desperate need for water and a bathroom break because I’ve already annoyed everyone enough for one night.

At least I made it. Tomorrow is a new day.