First Stop, Chicago

A shot of the Chicago skyline from the water. Many skyrises stand out against the bright blue water and cloudless sky.

My first real travel experience was after my high school graduation.

As a girl living on the outskirts of Toronto, a girl who loved the days she got to visit the city, I’ve always been the girl who gets gaga over New York City.

Growing up, my family never had a ton of money to spend on us, but I was turning 18 and my dad wanted to take me on a trip to celebrate the end of high school and the beginning of university, but we couldn’t afford the New York thing, so we did the Chicago thing.

And in a way, this was the best place to start me on travel.

A bright red arch leads onto a pier, reading "Navy Pier Dock Street".

This post is based purely on memories from almost 10 years ago, so sorry if it’s lacking detail.

Chicago is actually very similar to downtown Toronto in a lot of ways — bustling city near the water, lots of people to see and neat places to check out. I remember thinking it was a lot cleaner than Toronto, the area we stayed anyway. I remember walking a lot. My legs were always tired but my eyes were always lit up.

Sure, the cities were similar, but the fact that I got to take an hour plane ride meant Chicago felt so much further away. I led a sheltered life until this point, so jumping on a plane in one place and hopping off it in another felt like magic. Like maybe this was another world. And I had a ticket to see it.

My favourite part about being in Chicago was the water. And maybe this is when I learned that I loved it so much. We took a lot of water taxis to get places and ended up on a lot of very cheesy tours, but my eyes were constantly drawn to the skyline.

The classic CHICAGO sign in bright neon lights at nighttime.

My dad, my sister and I ended up doing a lot of the touristy things you do in Chicago — tried deep dish pizza, checked out Navy Pier, saw a musical, visited the aquarium and Sears Tower and the science museum. Those things were fun, but as my first travel experience, it struck me as weird. I don’t do those things in Toronto, and I’m from there. I wanted to see the places I visited the same way I saw home: appreciating all its beauty in its natural state. Not forced tourist traps.

So the touristy things were pretty fun, and I don’t regret doing them, but I knew that in time, if I ever got a chance to get on an expensive, magical plane again, I’d go somewhere I wanted to see, and I’d bring my camera, and I’d wander and just find things that made me smile. Because that’s kind of the way I see the world.

We’re all people on this rotating sphere and we’re all connected, and it is so awe-inspiring. I want to see nature and architecture and people and culture. Not at a museum, but throughout the places I visit.

A cityscape view from a bridge. The city is divided by a large river, boats sailing along.

I’ve always been a lover of photography, and travelling was the first time I was encouraged to take photos instead of being mocked for carrying my camera.

That was back in 2009 where people had shitty cameras on their phones and all I owned was a teeny Nikon point-and-shoot digital. Back when Facebook was just starting up and Instagram wasn’t nearly as popular (if it was even a thing at that point). People didn’t just whip out their cameras, and if you did, you usually got told to put it away because no one liked their photo being taken.

Enter a new digital age, and my adult life, where it’s totally fine for anyone to take a quick picture with their smartphone. I can’t wait to continue travelling, if not for the sole purpose of exploring my love of photography and seeing the world through my viewfinder.

Highlights of my first real travel experience:

  • Discovered my love of being near the water;

  • Encouraged my love of photography;

  • First trip on a plane;

  • First trip using my passport;

  • Best steak I’ve ever eaten;

  • American iced tea (not automatically sweetened, like in Canada!); and

  • Knowing this wouldn’t be the last time I’d travel.

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Florida: Disney World and Universal Studios, 2011

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