On a trip to Montreal, my first time ever in Canada, I ditched ChatGPT and influencer travel content for actual recommendations from locals.
As a travel writer and content creator, I draft an itinerary before I travel. Every day is carefully curated from when I wake up to when I go to sleep, including dining reservations, sightseeing, and other activities. I spend hours scouring the internet, TikTok, and Instagram for Top 10 and “Best of” lists, and asking ChatGPT for recommendations.
It’s become exhausting.
I have to sift through each post and ask myself whether the influencer genuinely enjoyed the place they’re reviewing, or if it’s just an advertisement — or, alternatively, if they’re purposely highlighting something negative for engagement and exaggerating the experience. Also, articles ChatGPT recommends sometimes haven’t been updated in years, and a place you added to your list may no longer even be in business.
So, to test a new way of traveling, I decided to book an overnight stay in Montreal during a layover. I booked my flight, and that was the end of the planning. Equipped solely with a destination, my Midwestern ease with small talk, and an interest in genuine recommendations, I went on my trip with no itinerary and no pre-planning.
I got my first recommendations while waiting for my flight
As I waited to board my flight, I decided it was as good a time as any to ask for travel tips. I struck up a conversation with a man at my gate and asked where he recommended I stay. His eyes widened when I told him I was heading to a new-to-me country and had not secured a hotel, but he was excited to walk me through the neighborhoods of Montreal.
His first recommendation was Old Montreal, the heart of the city, which is the perfect location for walking to both the Old Port and to sights such as the Notre-Dame Basilica. He also recommended Downtown Montreal for great shopping and easy transport, and Griffintown, with its vibrant art scene of Montreal, as possibilities. Given that I had just about 24 hours, I decided to book a hotel in Downtown Montreal because it had bustling streets and wasn’t too far from the airport.
My Uber driver also had some tips for me
Then on my ride from the airport, I got more tips. When I told my Uber driver that it was my first time in the city, he immediately launched into a list of reasons he loves Montreal. He recommended a few activities, like going to Ye Old Orchard Pub and Grill to watch a hockey game, trying some of the iconic smoked meat and poutine that Montreal has to offer, and checking out the bars in the entertainment district. By the time I arrived at my hotel, I had a list full of personalized recommendations that took just a few minutes of active, engaged listening, rather than hours of scrolling.
After checking into my hotel, I went off to my first recommendation from my Uber driver — Schwartz’s Deli, one of the oldest delis in Canada. I was in foodie heaven as I went to town on a delicious smoked meat sandwich worth every minute I had to wait in line to get a seat.
I also got a recommendation from the cashier at Schwartz’s Deli
Surprisingly, my next recommendation came from the cashier as I was leaving. She inquired about my meal, and I told her how much I loved what I ordered, but that I regretted not going for one of their other classic dishes. She immediately recommended another one of Montreal’s popular food spots, La Banquise, and told me not to leave without trying their poutine.
From there, I took a tip the hotel staff had given me when I checked in (yes, I talked to them too!) and walked to the Old Port of Montreal. I used the walk as a chance to explore the city and made several stops along the way, spotting bits of history like Notre-Dame Basilica of Montreal, Montreal City Hall, and Quebec’s oldest private historical museum, Chateau Ramezay. I also snagged some sports gear for my dad, from Montreal’s Hockey team, the Montreal Canadiens (also known as the Habs).
I ended the day full of poutine and satisfied with the results from my adventure. No, I couldn’t see everything Montreal has to offer in 24 hours, but my quest to “talk local” saved me hours of planning and allowed people who know the city best to share what makes their home so special.
Itinerary-free travel isn’t for every trip, but it worked perfectly for this one
Now, do I recommend an itinerary-free method for every trip? Absolutely not. Montreal was a unique test for this experiment for a few reasons. First, as the second-largest city in Canada, I knew booking a hotel would be a breeze. If I were going somewhere smaller or more remote, I would not chance a last-minute hotel booking.
It was a long layover with time constraints, which, ironically, gave me a sense of freedom. I didn’t pressure myself to make reservations or book a fancy hotel. I simply strolled on my own time, stopping and perusing any shop I fancied and recommendations I picked up along the way.
I can admit my itinerary-free planning isn’t a path to follow for every trip, but I do hope to incorporate the importance of flexibility and “go with the flow” in my travels and skip or at least limit the overload that comes with endless scrolling to plan.
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