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It seems ridiculous that, for a girl who’s done a fair bit of travelling to far off places, I’ve never been to Mexico or Canada. Well, this summer I finally crossed one of those countries off my list and made it up to Canada on a road trip with my boyfriend. Our first stop was four days in Toronto, and we absolutely fell in love.

Day One

The vast majority of the first of our four days in Toronto was taken up by driving. We made it all the way from Chicago through Michigan, the border, and middle-of-nowhere Ontario before finally arriving in the city with our stomachs growling for food.

Deciding to do the sensible thing and get some dinner before we died of starvation, we headed to Levetto, a small Canadian chain restaurant with delicious Italian food and reasonable prices (homemade noodles? Yum!) 

Levetto Toronto

Absolutely stuffed from the huge portion sizes, we took a short walk around the neighborhood. Despite the fact that our next stop was directly across the street from where we had had dinner. This turned out to be an excellent choice because not only did it allow us to digest before stuffing our faces with doughnut ice cream cones, but it provided us with an excellent introduction to the city of Toronto. We could already see how multi-cultural the place was, with a million different types of food sold on every corner. We laughed as a man raced his girlfriend down a residential street while several really cute dogs looked on. Life was good.

Finally, we found our way back to Sudbury Street and Eva’s Original Chimney’s – the food truck famous for serving soft serve ice cream in cones made out of doughnuts. This was literally the only thing that my boyfriend asked to do on our entire trip. And boy did he make an amazing choice. Even though I was ready to throw up by the end of it and couldn’t finish my cone, they were seriously delicious, Instagram worthy, and the perfect ending to our short introduction to Toronto. 

 Day Two

Not wanting to waste a single second of our first full day in Toronto, we headed out bright and early. We made a beeline to the Royal Ontario Museum. While there, we had our minds blown by just how much stuff was housed there. We also completely maturely pretended to be dinosaurs more than a few times.

There were some great Canadian history exhibits which we made sure to spend plenty of time in. We felt we should probably get a decent idea of the history of the place we would be staying in for the next week or so.

 Royal Ontario Museum Toronto

From the Royal Ontario Museum we moved on to Chinatown and Kensington Market. We wandered through the shops, gaped at ducks hanging up in the windows, and enjoyed the fabulous hipster-ness of an artisanal iced tea shop (where I’ll admit I caved and made a purchase).

Chinatown Toronto

The Toronto Waterfront

Since we had a bit of time before our next planned stop of the day, we decided to hop on a streetcar and spend our afternoon on the lakefront. It didn’t take very long for us to settle into our lazy habits. We found a bench to sit on and took the opportunity to rest our already sore feet (I had acquired some pretty crazy blisters from making the stupid decision to break in my new Birkenstocks while we were in Chicago).

Boat Toronto Waterfront

tiki Taxi Toronto Waterfront

We had a good laugh at the Tiki Taxis that were coming and going from the harbour, ferrying people off towards the Toronto Islands. My boyfriend yelled at seagulls while I tried to defend them (though really, I have no ground to stand on in this argument). And of course, we caught continuous glimpses of the CN Tower as we wandered through the maze of boats.

CN Tower Toronto Waterfront

Addie Toronto Waterfront

Boats Toronto Waterfront 

After our somewhat lazy afternoon exploring the lakefront, we embarked on the confusing journey to the Distillery District. This was a journey which required walking, a streetcar, more walking, and more walking. So by the time we reached our destination we were absolutely starving.

The Distillery District

Of course, it being a Friday night, the restaurant where we were planning on eating at was absolutely packed. And so was every other restaurant within a mile radius. After a short breakdown and with no food in sight, we caved and splurged at the one restaurant within walking distance that didn’t have a line.

The portions were tiny but the food was good. And all that really mattered to us was that there was food. And that we weren’t going to have to wait more than an hour to get it.

With our bellies full and our energy refueled, we were finally able to appreciate the beauty of the Distillery District. We walked around during sunset, and it was honestly pretty gorgeous.

Distillery District Toronto Gooderham & Worts

Distillery District Toronto Clock

Distillery District Toronto Barrels

We actually got a two for one deal on the beauty of the Distillery District when we realized halfway home that we had left my bag of artisanal iced tea at the restaurant. Of course, we had to promptly turn around and go get it. That stuff was expensive and we had bought a day pass for the public transportation. So I was not about the leave it behind.

And thus was the end of our second day in Toronto. Continue reading my next post to hear about our last two days in TO!

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Read all about what we did in our first two days in Toronto, Ontario, Canada - and get some itinerary inspiration for your own trip! | Four Days in Toronto


Addie Gray is a recent college grad and a passionate solo female traveler. Having traveled to more than 20 countries, she now shares her knowledge on budget travel, solo female travel, and travel photography.

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