TORONTO — Sometimes, the best trips are the ones where you have absolutely nothing planned.
That’s exactly what happened when I decided to take my 15-year-old son, Gregory, on a quick weekend getaway outside the United States.
With his passport finally in hand, I wanted to give him an opportunity to experience international travel. Not necessarily some elaborate vacation filled with sightseeing tours, expensive attractions, or a packed itinerary. I simply wanted us to get away for a couple of days, spend some quality time together, and explore somewhere different.
Of course, my search landed us in the Great White North, specifically Canada’s largest city, Toronto.
Located along the northwestern shore of Lake Ontario, Toronto is one of North America’s most diverse cities, with a population of nearly 3 million people. It’s also a relatively easy international getaway from Chicago, with nonstop flights taking less than two hours.
For those unfamiliar with Toronto, the city offers a little bit of everything: world-class restaurants, professional sports, museums, shopping, entertainment, and a vibrant downtown that stays busy well into the night.
But we weren’t necessarily interested in checking off a list of tourist attractions.
We had very little planned, and as it turned out, that made the trip perfect.
A Late-Night Arrival in Canada
On a Friday evening, Gregory and I boarded a nonstop United Airlines flight from Chicago’s O’Hare International Airport to Toronto Pearson International Airport.
Our flight was scheduled to depart at 9:20 p.m., putting us in Toronto shortly before midnight.
It was Gregory’s first opportunity to put his new passport to use, and I was excited for him to experience the process of entering another country.
Admittedly, I had some concerns about what to expect when we arrived.
As a NEXUS cardholder, I’m accustomed to a relatively seamless experience when entering Canada. For those unfamiliar, NEXUS is a trusted traveler program jointly administered by U.S. Customs and Border Protection and the Canada Border Services Agency. It allows preapproved, low-risk travelers to use expedited processing options when crossing the U.S.-Canada border.
Typically, I scan my card, complete the necessary identity verification, and continue on my way.
However, traveling internationally with a minor can introduce additional considerations, particularly when only one parent is accompanying the child.
During my research, I learned that Canadian border officials may request documentation establishing the accompanying adult’s relationship to the child or permission from a parent who isn’t traveling. Canada recommends that children traveling with only one parent carry a consent letter from the other parent, when applicable.
A consent letter isn’t universally required by Canadian law, but border officials have discretion to ask questions or request supporting documentation.
Fortunately, none of that became an issue during our visit.
Since Gregory wasn’t a NEXUS member, we used the regular arrivals process instead.
We approached the airport kiosks, took our pictures, answered a few questions and received printed receipts. From there, we continued through the arrival process without any additional complications.
Just like that, we were officially in Canada!
Because we were only visiting for the weekend, we traveled with carry-on luggage and didn’t have any checked bags to retrieve.
We headed downstairs to the airport’s ground transportation area and requested an Uber to our hotel in downtown Toronto.
The ride cost approximately $34 USD.
For travelers planning a similar visit, Toronto Pearson is located outside the downtown core, so getting into the city will take additional time. Depending on traffic, the drive can take roughly 30 to 45 minutes or longer.
There’s also the UP Express, an airport train connecting Pearson to Union Station in downtown Toronto in approximately 25 minutes. It’s worth considering for travelers looking to avoid traffic or save on transportation costs.
For us, though, arriving close to midnight with luggage and a teenager in tow made Uber the easiest option.
Checking Into the Marriott Downtown at CF Toronto Eaton Centre
Our home for the weekend was the Marriott Downtown at CF Toronto Eaton Centre, a full-service Marriott property in the heart of downtown Toronto.
One of the biggest advantages of staying here is the location.
The hotel sits near CF Toronto Eaton Centre, one of Canada’s busiest shopping destinations, and within walking distance of several major downtown attractions, including Nathan Phillips Square, Toronto City Hall, and Yonge-Dundas Square.
For visitors who want to explore Toronto without constantly relying on rideshares or public transportation, this area is an excellent starting point.
After checking in and getting settled, most people probably would have gone straight to bed.
Not us.
It was already well past midnight, but neither of us was particularly interested in calling it a night.
Instead, we pulled out our phones and started Googling restaurants that were still open nearby.
That’s when our first Toronto adventure began.
Burgers, Bright Lights and a Little DMX
We headed out onto Dundas Street, where the surprisingly warm fall weather made walking around downtown rather enjoyable.
Eventually, we reached Yonge Street and the surrounding entertainment district, an area that immediately reminded me of Times Square in New York City.
The intersection of Yonge and Dundas is one of Toronto’s most recognizable gathering places. Known for its massive digital billboards, illuminated storefronts, restaurants, and constant pedestrian activity, the area has long served as a popular meeting point for residents and tourists.
The public square at the intersection, formerly known as Yonge-Dundas Square, was renamed Sankofa Square in 2024.
Even at that hour, the neighborhood was buzzing.
Hundreds, if not thousands, of people appeared to be out enjoying the night. Many businesses had already closed, but that didn’t seem to matter. People were walking around, talking, taking pictures, and simply enjoying the atmosphere.
There was something about the area’s energy that made it feel as if the city had no intention of going to sleep.
Eventually, we stumbled upon Firefly Burger Toronto, a burger restaurant that was still serving food into the early morning hours.
Now, I should mention that Gregory and I generally try to be mindful of what we eat.
But we were on vacation.
And sometimes, vacation means throwing your usual eating habits out the window.
We ordered thick cheeseburgers and fries, and Gregory added mozzarella sticks to the mix.
I was feeling particularly adventurous and even ordered a pop!
Yes, a regular pop.
Now you know I was having entirely too much fun.
The food was good. The burgers were juicy, the fries hit the spot, and after traveling all evening, we were more than happy to have something substantial to eat.
However, the bill was another story.
Our late-night meal came to nearly $60 CAD.
For a couple of burgers, fries, and some extras, that felt pretty steep.
One thing American travelers should keep in mind when visiting Canada is that prices are displayed in Canadian dollars. Depending on the exchange rate, the amount charged to a U.S. credit card may be noticeably lower than the amount on the receipt.
Still, even accounting for the currency difference, this wasn’t exactly a budget-friendly burger run.
But we were full, happy, and enjoying ourselves, so I wasn’t about to let the price ruin the evening.
Besides, the night was far from over.
As we started walking back toward the hotel, we could hear music blasting from a nightclub along Yonge Street.
And not just any music.
DMX’s “Party Up (Up in Here)” was playing.
Now, anyone who knows that song knows it’s nearly impossible to hear it without getting a little excited.
Gregory and I looked at each other, and before I knew it, we were having our own little party right there on the street.
We danced, laughed, and enjoyed the music coming from the club.
No tickets. No cover charge. No plans.
Just a father and son turning up in downtown Toronto.
What started as a quick walk to find something to eat had turned into an unexpected late-night adventure.
We continued hanging out and enjoying the atmosphere until somewhere around 2:30 or 3 a.m.
At that point, even I had to admit it was time to get some sleep.
We headed back to the Marriott, bringing our first night in Canada to a close.
And honestly, if that had been the only memorable thing we did all weekend, I still would have considered the trip worthwhile.
Breakfast for Lunch and a Visit to Toronto City Hall
The following morning — or perhaps I should say afternoon — we woke up feeling exactly like two people who had been out partying until nearly 3 a.m.
There was certainly no rushing to get out of bed.
Eventually, we got ourselves together and headed to the nearby Denny’s on Dundas Street.
Yes, we traveled all the way to Canada and ended up eating at Denny’s.
Sometimes, familiarity wins.
We enjoyed breakfast for lunch, which was exactly what we needed after our late-night adventure.
With our stomachs full, we decided to walk around downtown and see what we could find.
Our next stop was Nathan Phillips Square, the large public plaza outside Toronto City Hall.
The square is one of the city’s best-known public gathering spaces and regularly hosts concerts, festivals, cultural celebrations, and community events throughout the year.
During the winter, its reflecting pool transforms into an outdoor skating rink, making it a popular destination for residents and visitors.
It’s also home to one of Toronto’s most recognizable photo opportunities: the illuminated TORONTO sign.
Naturally, we had to stop and take a few pictures.
One of the things I appreciated about downtown Toronto was how easy it was to explore on foot.
We weren’t following a carefully planned route or trying to make it to a particular attraction by a certain time.
We simply walked, talked, and stopped whenever something caught our attention.
And for a trip like this, that was more than enough.
A Little Shopping at CF Toronto Eaton Centre
After spending some time around City Hall, we made our way to CF Toronto Eaton Centre.
If you enjoy shopping, this is one place you’ll probably want to visit while in Toronto.
The massive multilevel shopping mall occupies several blocks in the heart of downtown and features hundreds of stores, restaurants, and services.
It’s also one of the city’s major tourist attractions, drawing millions of visitors annually.
From international fashion brands to electronics, specialty retailers, and familiar North American stores, there’s no shortage of places to spend money.
And apparently, Gregory had every intention of helping me do just that.
To our surprise, a LEGO store had recently opened at the mall, and there was a long line of people waiting to get inside.
Now, if you know Gregory, you know he loves LEGO, particularly the cars.
So naturally, there was no way we were going to walk past that store without stopping.
After waiting and making our way inside, he found another LEGO car that he wanted to add to his collection.
And, of course, I bought it.
Because apparently, that’s what dads are supposed to do.
We spent some additional time window shopping and exploring the mall before deciding we’d had enough excitement for the afternoon.
One of the benefits of staying at the Marriott Downtown at CF Toronto Eaton Centre was that we didn’t have far to walk to get back to our room.
Within minutes, we were back at the hotel.
Sometimes Doing Nothing Is the Best Part of a Vacation
Now, here’s where some travelers might find our itinerary a little unusual.
After spending part of the day exploring downtown Toronto, we decided we didn’t particularly feel like doing anything else.
We didn’t visit the CN Tower.
We didn’t take a sightseeing cruise on Lake Ontario.
We didn’t venture over to the Royal Ontario Museum or try to squeeze in another major tourist attraction.
Instead, we went back to our hotel, relaxed, watched movies, and eventually ordered pizza.
And you know what?
It was wonderful.
There was no pressure to get dressed and head back outside. No reservations to keep. No attractions we felt obligated to visit simply because we’d traveled to another country.
We were perfectly content spending the evening relaxing in our hotel room.
Sometimes, I think travelers put so much pressure on themselves to see and do everything that they forget vacations are also supposed to be relaxing.
There’s nothing wrong with wanting to experience as much as possible, especially when visiting somewhere for the first time.
But there’s also something refreshing about having the freedom to do absolutely nothing.
For Gregory and me, that was exactly what we needed.
The Best Part of Toronto Had Nothing to Do With Toronto
Looking back on our weekend, I realize that from the outside looking in, our trip probably wasn’t anything particularly spectacular.
We didn’t spend hundreds of dollars on attractions.
We didn’t have an elaborate itinerary.
We didn’t visit every famous landmark or experience everything Toronto has to offer.
Our weekend consisted of walking around downtown, eating burgers, dancing to DMX in the street, taking pictures, shopping for LEGO, and watching movies in a hotel room.
And somehow, it was one of those trips that reminded me why I love traveling so much.
For Gregory, the excitement wasn’t necessarily about what we were going to do once we arrived.
It was about going to Canada.
It was about having his passport, boarding an international flight, entering another country, and being able to say he’d experienced somewhere outside the United States.
At 15 years old, those experiences matter.
Travel has a way of showing young people that the world is much bigger than the communities they see every day.
It introduces them to different places, cultures, and ways of life. It encourages curiosity and, hopefully, creates a desire to continue exploring.
But beyond the international travel experience, I appreciated having the opportunity to spend time with my son without the distractions and responsibilities of our everyday routines.
There were no schedules to manage, no appointments to rush to, and no obligations demanding our attention.
For a couple of days, it was just us.
And as Gregory gets older, I’m becoming increasingly aware of how valuable those moments are.
He’s already 15. Before I know it, he’ll be graduating from high school, making plans for his future, and becoming more independent.
That’s why experiences like this mean so much to me.
Years from now, he might not remember what we ordered at Firefly Burger or which LEGO car he picked out at the mall.
But I hope he remembers walking through downtown Toronto with his dad in the middle of the night, laughing and dancing to DMX without a care in the world.
I know I will.
Before our trip ended, Gregory and I agreed that Toronto was just a preview of what’s to come.
There are more cities to explore, more countries to visit, and plenty of memories still waiting to be made.
And if this weekend taught me anything, it’s that we don’t necessarily need an elaborate itinerary to make those memories.
Sometimes, all it takes is a couple of plane tickets, a hotel room, and the willingness to see where the day takes you.
After all, the best part of traveling isn’t always where you go. Sometimes, it’s who you get to experience it with.
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