I had to enter the United States again last week, this time at the land border (and unexpectedly). Andrew, Flytrippers’ other co-founder, had already shared my first experience entering the United States in early May along with his own, but those were all by air.
He talked about the survey that says 82% of Quebecers are “afraid” to cross the border (it seems likely it’s similar elsewhere in Canada), so here’s another attempt to address this.
Here’s my experience entering the United States at the land border last week.
My experience at the land border last week
My entry to the United States in early May was to visit my American girlfriend’s family, before we visited mine in Canada after several months in South America (we are full-time digital nomads).
Last week, a family emergency meant we had to return to the United States. This time, we crossed the land border for the first time in a long time.
Here’s how it went:
- Exactly like the dozens of times before
There are almost 2 million Canadians who entered the United States in April 2025 alone (not counting millions of other nationalities).
So as Andrew said in the article that has lots of data and shares from our extensive experience with borders having visited nearly a hundred countries each… obviously there’s very little risk in going to the United States if you want to go or if you need to go, and the bad experiences that are mediatized (like our own experiences or yours) are entirely insignificant when almost 2M Canadians entered the country in April alone.
The media loves to talk about Trump and the United States as you’ve noticed, so if there were frequent problems, with 60,000 Canadians PER DAY entering there… we would know. Don’t worry, they would talk about it every day…
In my opinion, the numbers must be the same as before in terms of problems, but now each case becomes a case of interest for journalists and they publicize them, unlike before (like when Andrew spent more than an hour in an interrogation room… under Obama).
All the cases that were mediatized were not for tourism trips either!
So my experience was quite normal, like that of the vast majority of Canadian travelers who go there for tourism, just like before Trump.
But I still wanted to share an experience specifically for the land border, since Statistics Canada’s April data shows that the decline in Canadian travelers to the United States is much more pronounced by land (-35.2%) than by air (-19.9%). This isn’t surprising either, given that there are more business travelers by air.
More specifically, the border officer asked us the 3 most typical questions:
- Where do you live? (the hardest when you don’t live anywhere!)
- What are you coming to do?
- How long are you staying?
And that’s it. Very quick and efficient.
As Andrew rightly mentioned in the tips section of his article, as digital nomads, we weren’t 100% honest about the “where we live” part because that’s always to be avoided, in any country, and when any president is in power in the United States. That’s the basics.
We were also in a rental car, and he didn’t care about that either, just like the rest. He didn’t ask for papers or proof of anything.
For much more information on why it doesn’t make sense to be “afraid” of the border, you can read the detailed article on entering the United States as a Canadian.
By the way, thankfully, I paid for my rental car with a good credit card that has damage insurance included for free!
Because the recent American storms damaged the rear windshield of the rental car.
Besides our testimonials of business class flights for less than economy class (with Aeroplan points or with Avios points), I’ll soon share a testimonial of my credit card insurance claim, too, if you’re interested.
Free insurance is an excellent benefit of the world of travel rewards (for free hotels during delayed flights, trip cancellations, etc.)! As if all the free travel you get thanks to rewards wasn’t enough!!!
By the way, we strongly recommend taking advantage of the offer of $1025 free in simple points, which also gives 4 free passes for VIP airport lounges. It’s one of the best offers ever seen for simple points redeemable for almost any travel expense, with no restrictions or complexity.
It’s also an excellent offer to finally get started in this wonderful world. And like all good cards, it has insurance for rental cars to avoid paying for something you can get for free so easily!
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Summary
My experience entering the United States at the land border was as normal as our 4 entries by air since Trump’s return, unsurprisingly. Just in April 2025, there were 1.8 million Canadians who entered the United States (60,000 per day). The vast majority of Canadian travelers who go there for tourism have no problems, just like before Trump.
What would you like to know about entering the United States by land border as a Canadian? Tell us in the comments below.
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Featured image: U.S.–Canada land border (photo credit: Kevin Gagnon/Flytrippers)
