A Whimsical Week in Montréal: The Beauty of No Itinerary


North America

This post was contributed by Thomas Wiegand.

I consider myself a very organized and structured person, however when final exams roll around my usual habits tend to go out the window. Trust me, all my college students out there understand. When the going gets tough and finals season is upon us, you’re just trying to do everything you can to keep your head above water. I had booked a trip to Montréal over a month ago for the sake of having some time to relax and find myself again after this whirlwind of a semester, but I hadn’t planned a damn thing. It was the day before my flight, and I remember finishing my last exam and talking to my friend saying “Wow, I should really pack and plan out what I want to do.” That kind of became the essence of this trip for me, and let me tell you, having no plans can be a very beautiful thing.

I’m all for spontaneity, but normally when I’m visiting a new city (and especially in a different country) I try to map out routes to any places of interest and at least have a general idea of how to make the most of my time there. All that I really knew of Montréal, going into this trip, came from the fact that I had binged and re-binged all of Damon and Jo’s videos on their time in the city. Still, I didn’t have a clue what I wanted to do except for a few things like trying poutine, visiting the best two bagel shops in town, and climbing the mountain for that famous panoramic.

Oh, and something else I should probably mention – this was my first time ever staying in a hostel. I’m an avid lover of Airbnb, and most of my time abroad has otherwise been spent with host families that I’ve worked for. I’ve never ventured into the realm of hostel living, but it seemed like the time to do it. It definitely did not disappoint. I had breakfast included every morning, a rooftop Jacuzzi with a view of downtown, and the friends that I made as a stranger in this 14-bed dormitory. I was living the life. 

Meet Max, Kyle, and Johnno (photo below). Three Aussies and an American walk into a bar. Literally. That’s the punch line. These three guys started off my unplanned adventure by inviting me out the first night that I arrived in Montréal. I had no clue who they were, but pretty soon we were talking “America vs. Australia” over a bowl of vermicelli at the restaurant across the street.

My newfound friends are the sort of guys to seek out adventure wherever they go. The majority of the time, adventure looked like a trek by Max out onto the frozen bay. Crazy moments like this became the norm very quickly. One morning, we set out to make the famous trek up Mont Royal to see the city from above. Thanks to the rec from Damon and Jo, we made a pit stop at St-Viateur for one of Montréal’s most famous bagels.

Disclaimer: I tried the arguably just as famous Fairmount bagel and didn’t quite like it.

You can visit the shop where they make the bagels or the café in the trendy Mile End neighborhood. Personally, I opted for the café. The bagels are more expensive, but you’re also paying for the experience of a curious little diner and the chance to sit and enjoy it with friends. More often than not, the guys would turn to me immediately anyone was going to speak to us, always assuming that it would be in French. As the only one in the group who spoke French, I always obliged and translated the menu as many times as needed so that everyone could get their order straight. What’s comical about it is that Montréal functions as a completely bilingual city. I would wager that any English speaker could take care of themselves in Montréal just fine without any French.

Having no plans can be a very beautiful thing.

Max, Kyle, and Johnno

The first few days in Montréal spontaneous and memorable. They were the perfect people to share my trip with – always down to grab a beer, tour that church, or wait for the perfect sunset lighting at the top of Mont Royal to get the best Instagram moment. Most of our nights were spent braving the cold in the rooftop Jacuzzi, admiring the skyline and comparing taste in music. The last night that we were all together in Montréal, we spent longer than usual in the hot tub and saw a surprise firework show over the river. It’s moments like these when you finally decide to Shut Up and Go that make the grind of school and work that seems to never end so worth it.

The beauty of meeting complete strangers while traveling is that it forces you to be introspective.

I got so many questions about Americans and learned the ins and outs of Australian slang along the way (like how brekky = breakfast). It made me think about myself and the people around me that I consider ‘normal’ in so many new ways. Most importantly, I made a type of connection that I think is so unique to solo travel.

When you’re completely alone, you’re more approachable. People are likely to want to get to know you, and you’ll usually feel more inclined to make friends and explore when you’re not surrounded by your posse from back home with a full-fledged five-day plan to see everything in the city.

But the fun didn’t end there. Once my new friends had left Montréal to continue their trip throughout the States, I still had a few days left to tour the city. I spent my time in the botanical gardens admiring the flowers, making trips to St. Joseph’s oratory and other nearby cathedrals to admire the architecture, and walking along the river in the Old Port.

On my last night, I decided to meet up with a guy I had met on Tinder.

Cue the suspense.

We wanted to go to a drag show at Cabaret Mado where I had read that the best shows in town happened, so we met for a couple of glasses of sangria and made our way to the club. Canadian drag did not disappoint. If you’re a French learner, seeing a sassy drag queen talk and perform in French is quite the experience. We both laughed and laughed at our inability to sometimes catch what people were saying in the Québécois accent. At one point, we turned to a bartender for a few shots and she looked me dead in the eye and asked “T’es français?” Super confused, I replied in French and said “No. I just wanted to know how much for a shot. I’m American.” She laughs at the traditional accent I’ve been learning since grade school and tells me how much it’ll be in euros. I insist again that I’m American, to which she gives me a better reaction than before, and I just try to laugh it off. I couldn’t help but think how weird it is that we’re all trying our hardest to clock each other based on the way we talk. It’s not like traditional French, that I learn in school, and Canadian French are different languages at the end of the day – even still, people are so quick to pick a side when it comes to the pride of one’s own accent.

That whole situation turned into an hour-long conversation about linguistics as we stumbled our way through the Village looking for a shop that was open and serving poutine. I had made it almost an entire week without trying this Canadian delicacy of fries, gravy, and cheese. My new friend Decker insisted, so we popped into the A&W root beer shop of all places.

“A&W is a rough place in Canada at 3 am.” His words, but my thoughts exactly.

I had no business going on a quest to Camelot for some fries at 3 in the morning, but why not? That’s what travel is all about. With a belly full of poutine, we set out to the Old Port to see the Ferris wheel and the river. Stumbling your way through cobblestone streets at night in a foreign city is certainly one of the best feelings ever.

Have the courage to meet new people. Go on that date. Push your limits and explore the city (even if you know you have a flight to catch the next day) because I promise, you won’t regret it.

Until next time,


In the case of solo travel, spontaneity is your best friend.

Meet Thomas: I’m a 20-year-old college student from Chattanooga, Tennessee studying French and Environmental Science. I’m a researcher, language enthusiast, and travel junkie of course. Travel pet-peeve: When you try your hardest to speak the language and they still reply in English. Keep up with me on IG

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