How I Booked a $17,000 Trip to Japan for Under $100 Out of Pocket

I still remember the first time I realized credit card points were a thing. I stumbled onto a blog post from someone who flew first class to Europe for “just taxes,” and I was instantly obsessed. But once I started trying to do it myself, I hit every wall possible.

Back then, points felt like a secret code no one was really willing to explain. It took me two full years of trial and error, late-night research, and a lot of missed opportunities before I finally cracked the strategy that would change how I travel forever.

Fast forward to today - I just booked another trip to Japan (8th time!) with my partner worth $17,000, and we paid less than $100 out of pocket by having the right credit card points strategy.

Here’s exactly how we did it:

Flights: Business Class to Japan, Both Ways

✨ JAL Business Class (Outbound)

We booked Japan Airlines business class to Tokyo from LAX. US airlines could never beat that Japanese hospitality, if I'm being honest, so we fly JAL or ANA as often as we can!

✨ Singapore Airlines Business Class (Return)

Coming back, we redeemed points for Singapore Airlines business class, one of the most luxurious ways to fly long haul. The lie-flat seats, the satay skewers, the vibe? Unreal.

🏨 Hotels: 5-Star Luxury in Tokyo and Osaka

Conrad Tokyo

Our first stop is the Conrad Tokyo - a sleek, modern oasis right in the middle of the city. Massive rooms, stunning views of the bay, and breakfast that is always more like a Michelin tasting menu at Conrad properties.

Waldorf Astoria Osaka

Next up: the brand-new Waldorf Astoria Osaka. This place looks insane — ultra-refined interiors, personalized service, and the kind of calm you dream about after a day in Dotonbori. And the best part? We booked it entirely with points, making it a perfect example of Japan travel on a budget without sacrificing luxury.

💸 Total Value vs. What We Actually Paid

This entire trip – JAL and Singapore Airlines business class, 5-star luxury hotels, and unforgettable memories – would’ve cost us over $17,000 out of pocket.

Instead, we used about 580,000 points total for both of us.

That might sound like a lot – but when you’re using the best credit cards for travel rewards, maximizing the right transfer partners, booking the right dates, and stacking signup bonuses… it’s totally within reach, even if you don’t spend a ton. It only took us about 3 months to earn all of those points.

Here’s how we did it:

We follow a strategy I developed called the M.I.L.E.S. Framework — the same system I used to book free flights to Japan with credit card points, fly around the world in business class, and stay in hotels that would normally cost thousands… for pennies. I’ve now taught it to over 400 clients, and on average, they save $4,500+ per trip using this exact method.

✈️ Want In?

If you want to start learning how to do this too:

👉 Subscribe to the Cloud9 newsletter for tips to earn more points and travel in luxury without overspending.

Or if you’re ready to dive in head-first:

👉 Book a 1:1 strategy call with me and I’ll personally teach you the M.I.L.E.S. Framework, which is personalized to YOUR spending habits and travel goals, and help you build a customized plan to earn faster, find deals like the ones in this post, and start booking luxury trips with points.