Japan on Points (Part 2): Turning Points Into Hotel Nights in Japan

Mar 7

Planning to fly first class is only half the battle of planning our two-week trip to Japan. If you read Part One of this Japan series, I talk about the strategy that I’m using to try and get us First Class flights to and from Japan. But what about once we’re there? The biggest costs when travelling, especially to another country, is the flights and the hotel where you’re going to stay. You can definitely save on your accommodation costs based on where you choose to stay, but even then hotel costs still make up a decent amount of the budget. So, when my wife and I decided we wanted to go back to Japan, I told her a goal that I have was to have our flights covered and our hotels as well. By doing this we’d cut out the two biggest expenses of travelling to Japan and now any money that we would be spending on this trip would be for food and different experiences while we are in the country. Now, hopefully the dollar to yen conversion stays in our favor because having the two biggest expenses taken care of with points means this trip would become significantly cheaper.

The Key to Our Hotel Strategy

So how are we planning to do it? In this post HERE, I dive into the different types of points currencies, flexible points currencies and dedicated brand point currencies. Now in Part One of this Japan on Points series, I talked about how I plan on utilizing our flexible points currencies, Chase Ultimate Rewards and American Express Membership Rewards to book our flights to Japan. For our hotels I’m planning on going a different route. For some years now, I’ve been a dedicated Hilton guy. I started out with their free Hilton Honors card back in the day and eventually upgraded to the Hilton Honors Surpass card with American Express. This card has been my key to earning a lot of Hilton points since our last Japan trip in 2023. Not only are the multipliers decent, I also get complimentary Gold Elite status just for holding the card. Due to special rules during the pandemic and spend the year after that, I’ve actually had Hilton Diamond status for the past three years.

Before I dive further into how I’m planning to book hotels, let’s start with the current amount of points I have. Currently, I have 584,103 points to use towards our stays in Japan. How did I amass this amount of points? The first part of the equation ties with my status. As a general Hilton member, you earn 10 points per dollar on eligible spend at majority of Hilton properties (some of the brands under the Hilton umbrella only give you 5 points per dollar). As a Diamond Elite member, you earn 100% bonus points on eligible spend. This means that simply being a Diamond Member, I earn 20 points per dollar. Now that’s a pretty decent multiplier for spending at a hotel, but it gets better. When I use my Hilton Honors Surpass card, I get an additional 12 points per dollar on eligible spend at a Hilton property. This brings my points per dollar multiplier to 32 points per dollar. When my wife and I took our honeymoon a few years ago, the strategy was to pay out of pocket for our hotels as we had been gifted a generous amount from family and friends. We were in Europe for two weeks and as I mentioned above, once you get to your destination your biggest expense can easily be where you stay. If memory serves, after we took our honeymoon trip my Hilton account was well into the 100,000 range as every hotel we stayed at was a Hilton. Knowing we wanted to make it back to Japan, I would pay out of pocket for some of our smaller trips to keep stacking my Hilton points. At one point in early 2025, my point balance was around 750,000 points and was on track to cross 1,000,000. What happened you may ask? Well, when we took our next Europe trip in 2025 (the year after our honeymoon), I used about 280,000 points for a hotel my wife, her cousin, and I stayed in during our time in Brussels to help control the cost of our trip.

Points Earning and Strategy

So that brings us back to the here and now and what I’m planning for Japan in the Fall of 2026. The bulk of this trip will be in Tokyo, with a short stint up in northern Japan just outside of Sendai. Because of the ruralness of that part of our trip, we may have to pay for a cheap hotel for the few days we’re up there. But for the parts where we’re in Tokyo, the plan is that we can have our stays completely covered by points. Now Hilton hotels in Tokyo are not the cheapest from a points cost and due to dynamic points pricing, it can make rooms cost more points depending on when the trip is being booked. So how do I plan to go about this? I’m planning to utilize some of the benefits of my Hilton Honors Surpass card and my status with Hilton. Now with the Surpass card, when I spend $15,000 in a calendar year I earn a Free Night Award (FNA). Hilton FNAs are some of the most useful as they can be used at pretty much any property as long as there is a Standard Room available to be booked. At the end of 2025 I hit the $15,000 spend requirement and earned a Free Night Award. So, part of the plan is to use at least 1 Hilton FNA on our hotel bookings. Hopefully I’ll be able to earn at least one more so that I’ll have two to use. The next part of the strategy is to take advantage of Hilton’s 5th Night Free on Award Stays perk for Silver status and up. These two things right here could cut down my points cost significantly and allow me to book a nicer hotel for less points. The hotel that I’ve currently been eyeing is the Hilton Conrad in Tokyo, which from my research is typically around 130,000 points per night. The reason I’ve been eyeing this hotel is because it’s in the heart of Tokyo and Conrads are just one tier below Hilton’s top-tier Waldorf Astoria chain. Not a bad way to stay in Tokyo if you ask me!

Now you’re probably doing the quick math and are thinking “you’re going to need a lot more points if the hotel costs 130,000 points per night”. To that I’d say your absolutely right! And that’s why, like our points for flights, we are still accruing points until we’re ready to start booking our trip. That means I’m being as strategic as I can to make sure I’m optimizing the spend that is put on my Hilton Honors Surpass card. For example, I use that card to pay for gas each week because I earn 6 points for every dollar on gas. I’ve also been using it as my catch all card because it earns 3 points per dollar on all non-category spend. Now some may argue that Hilton Honors points aren’t the best when it comes to value to which I’d say you’re right. Typically, Hilton Honors points are usually valued around $0.006 per point. The reason that I’ve stuck with Hilton, and you can see this above, is because of the multipliers. It’s pretty easy to earn a lot of Hilton points quickly, so this is what works for me. And to be fully transparent, my wife currently has the free version of the Hilton Honors American Express card that we got a 100,000 point sign-up bonus for. And from spend that she had put on that card she’s sitting around 125,000 points. We stopped her spend on that card to focus on our flexible points currency on her Chase cards to help us with our First Class flight goal. And ideally I’d want to leave her points untouched so we have something for our next adventure after Japan. But, if need be, I can pool points with her to combine our points for an award booking to ensure we don’t have to pay for our hotels.

Conclusion

So that’s where we are right now when it comes to continuing to plan out our trip to Japan later this year. I hope that this is an encouragement to you on how to figure out how to use points to reach your travel goals. If you’re just starting out feel free to check out this post HERE, so you can figure out where to start your credit card journey to reach your travel goals. But hopefully this was more of a fun read where you can see how things can play out in real-life through real-life examples. I’ll look to continue this series so you can see the progress that my wife and I are making as we eventually get to booking things for Japan. Do you think we’ll truly be able to do all these things I’ve talked about in the first two posts of this series? Or will we fall short? Be sure to come back to the blog to see how things pan out.