It Started with a Flight Between Saskatchewan and Ontario
Back in 2016, I was flying frequently between Saskatchewan and Ontario for work. Those flights added up fast — and that's when I started digging into travel points. Aeroplan was exceptional in those days, and WestJet had member-exclusive redemptions that actually made sense. I was hooked almost immediately.
What started as a way to offset domestic flights quickly became something much bigger. Within a couple of years I was booking business class cabins across multiple continents — and paying next to nothing for them.
The Redemptions That Changed Everything
My first major hotel redemption was a Christmas and NYE stay at the Ritz Carlton Cancun — an experience that showed me just how far points could stretch when used correctly. But it was my first Mini Round-the-World trip with Aeroplan that really made me understand the power of knowing the rules.
That itinerary: Toronto → Brussels → Bangkok → Melbourne → Delhi → Chandigarh → Mumbai → Dubai → Frankfurt → New York → Toronto — all in business class, including a domestic Qantas business class leg across Australia. At the time, Aeroplan's Mini RTW was only 150,000 points per person. Most people didn't even know it existed.
My 2018 trip combining that Mini RTW with a stay at the Ritz Carlton Al-Hamra remains my personal favourite to this day. It set the bar for what's possible when you know exactly which programs to use, and when.
Meet the Little Canadian Traveller
My daughter is three years old. She has already clocked 45 flight segments — first class, business class, premium economy, and economy. She is, without question, the most well-travelled three-year-old I know.
She's the reason the name exists. @littlecanadiantraveller is her Instagram handle, and it captures exactly what this is all about — a Canadian kid seeing the world, one points redemption at a time. Every Christmas and NYE we head somewhere warm: Aruba, Bonaire, Curaçao, and this December we're heading to Bali. Tickets already booked.
All 10 Provinces — Right Here at Home
Most people think travel points are for international trips. I believe Canada itself is one of the most underrated destinations in the world — and I've backed that up by travelling to every single one of the 10 provinces.
Some of my most memorable trips have been purely domestic. I've stood on the shores of Newfoundland watching icebergs drift past — ancient ice that calved off Greenland glaciers thousands of years ago, floating quietly in the Labrador Sea. There is genuinely nothing else like it on Earth.
I've also made the trip to Churchill, Manitoba — the polar bear capital of the world. Watching polar bears in their natural habitat on the Hudson Bay tundra is a once-in-a-lifetime experience that most Canadians don't even know is accessible to them. Points made both trips possible.
Why Google Can't Do What I Do
People ask me all the time: "Can't I just Google this?" Sure — the same way you can Google a recipe and think you're going to cook like a five-star chef. The information exists somewhere, but knowing what to look for, where to look, and how to apply it to your specific situation takes years of experience that no search result can replicate.
A friend of mine once redeemed 140,000 points for a Vancouver to Istanbul ticket. I would never have let that happen for a client — not unless they were completely set on it after understanding the alternatives. Google didn't tell him about partner carrier routing, positioning flights, or the programs that could have done the same trip for half the points. That's the gap I fill.
I've had this conversation with CEOs, business owners, and busy professionals. One executive I worked with at a former company had never considered the US credit card ecosystem. After one conversation, he dove in completely. That's what 10 years of obsession looks like when it's applied in 45 minutes.
How I Think About Points
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