The trip that showed me what travel is supposed to feel like

I wanted to do something special for my girlfriend. Not just a trip — a real experience. Japan had been on both of our lists for a long time, and I wanted her first time there to feel like an arrival, not a recovery. That instinct led me down a rabbit hole that quietly changed everything.

I'd been researching points and award travel for a while, the way you do when you're convinced there has to be a smarter way to do this. And then I found it: Singapore Airlines allowed multi-city bookings with a stopover in Tokyo at no extra points cost. The whole thing — LAX to Tokyo, then onward to Singapore — for 214,000 points and $190 in fees.

For context, that same itinerary in business class would have run somewhere north of $10,000 in cash. Per person.

214k Points Used — $190 Cash Paid — 19 nights total

We flew Singapore Airlines the entire way. And from the moment we sat down — the whole seat to yourself, the dedicated storage, the large personal screen, the flight attendant arriving with champagne and a printed menu before we'd even pushed back from the gate — we both knew this was categorically different from anything we'd experienced in the air before.

“The trip doesn’t begin when you land. It begins the second you leave your house. The flight is part of the journey.”

That sounds obvious when you say it out loud. But most of us have spent our entire travelling lives treating the flight as something to survive — to white-knuckle through with a neck pillow and a downloaded series — so that we can arrive at the destination and finally begin. Sixteen hours in economy to Tokyo is an endurance event. You land exhausted, stiff, and already behind.

We landed rested. We'd eaten steak and lobster somewhere over the Pacific, had more champagne than was strictly necessary, and slept properly in seats that actually reclined flat. We stepped off the plane in Tokyo ready for the city, not ready for a hotel bed.

Tokyo. Osaka. Kyoto. Then Singapore for the race.

We spent six nights in Tokyo, three in Osaka, and three in Kyoto — a pace that let us actually settle into each city rather than rush through it. In Tokyo we stayed at the Mandarin Oriental, which set a standard for the rest of the trip that everything else had to live up to. Breakfast each morning with views across the city. Dinner at Tapas Molecular Bar, which was less a meal and more a two-hour theatrical experience. The Pizza Bar on the 38th floor on another night, which sounds casual until you're sitting above the Tokyo skyline with a glass of wine watching the city light up below you.

Then Singapore for the Formula 1 race — a genuine bucket list moment that I'll be honest, would not have happened without points. There is no version of that trip where I voluntarily spend 16 hours in economy, fly to Singapore, watch the race, and fly 16 hours home. The business class cabin made it not just possible but genuinely exciting from the moment we left the house.

“Once you start travelling this way, you can’t go back. It’s not about luxury for its own sake — it’s about what it makes possible.”

Then came Paris — and the number that changed everything.

A year or so later, we wanted to go to Paris. Of course we wanted to fly business class again — once you've slept flat across the Pacific, the idea of folding yourself into economy for any long-haul flight feels genuinely absurd. So I looked up business class to Paris.

Five to eight thousand dollars. Round trip. Per person. For a flight substantially shorter than Tokyo.

My reaction was immediate and simple: there is no way. Which meant, as far as I could see, no business class. And that stung — not out of entitlement, but because I now understood what we'd be giving up.

So I kept looking. And I found that Air France business class was bookable for 60,000 miles and $250 in fees. The availability opened, and I booked it the same day — even though the best flight departed from Dallas and we're based in Phoenix. We drove to Dallas. It was worth it without a second thought.

That moment — the disbelief at the cash price, the search, the find, the immediate booking — crystallised something I'd been circling for a while. The knowledge gap between what points can do and what most people think they can do is enormous. And on the other side of that gap is an entirely different relationship with travel.

What came after.

Since that first trip, we've been to Japan twice, Singapore twice, Hong Kong, Thailand, Korea, Paris twice, London, Switzerland, Dubai, and South Africa. Almost all of it in business class or better. Almost none of it at anywhere near the cash price.

I've helped my mother book business class. I've helped my girlfriend's family — including a sibling travelling with a three-year-old — fly business class back to their hometown in Johannesburg. If you've ever tried to manage a toddler on a long-haul flight, you understand immediately why a flat seat and real space is not a luxury in that situation — it's a completely different experience for the whole family.

Friends started asking how we were doing it. Then their friends. Then people I'd never met. The questions were always the same: I have points sitting in my account — what are they actually worth? Can I really fly like that? Where do I start?

That's what this journal is. The trips we've taken, the cabins we've sat in, the properties we've stayed at, and exactly how we got there. The redemptions that worked, the ones that surprised us, and the thinking behind all of it.

Because the trip doesn't have to begin when you land.

It begins the second you leave your house.