Bones Before Meat: How I Plan Japan Trips That Actually Work (Part 1 of 5)
How I approached planning a first trip to Japan for friends - balancing points, expectations, and leaving space for the unexpected.
First off, let’s answer that burning question on your mind: how did our friends have so many points? Below, let’s demystify how they accumulated so much, in so little time.
Six Months, Not Six Years
Brian earned a ton of American Express Membership Rewards points through his business expenses, timing his applications around a 200k Business Platinum offer and a 150k Business Gold he had opened months earlier.
The 200k Marriott points was earned by his wife, Whitney, through the Amex Marriott Bonvoy Brilliant 185k offer.
The 160k AA miles were through two separate applications for the Barclays AAdvantage Aviator Red 70k offers (this card is no longer offered, but the Citi AAdvantage Platinum Select card offers a similar mileage bonus).
The key takeaway: this wasn’t years of hoarding - but rather just six months of intentional applications timed around high offers.
Actually, I had recommended most of these cards to them in the months leading up to this very conversation, but I was still surprised by the sheer amount and diversity of miles in such a short time.
One obvious and rather powerful advantage that Brian has is that he has a business with real expenses, allowing him to apply for business cards and meet the minimum spend bonuses. (A future article will be published about why business cards are a massive plus to your award strategies, and why you shouldn’t assume you can’t have one)
But nowadays, with 175k Amex Platinum personal offers floating around regularly, it’s not hard to imagine that for the average couple who is serious about points-earning, these numbers are not hard to achieve (they can both get the same card and earn double the amount of points from sign-up bonuses).
Great. Now I’m Responsible
Did you know? Crabs have so many legs - but they can only move side-ways. That’s how I feel planing for my friends…
Back to our trip.
This wasn’t just our vacation - I felt responsible for shaping their first impression of Japan.And honestly? We’ve only known them for three years, but they’ve become such close friends to us since we all get along, not just when the guys are friends or vice versa.
The stakes were super high because we had never traveled with them before, and we knew they had so much more energy than we ever do. Plus, as amazingly chill as Brian is, occasionally his Queens, NY personality would come out - Whitney would tell us that he is quick to write something off if he doesn’t like it the first time.
Great.
Since we were spending almost two whole weeks with our first-time-to-Japan friends, I had to really try my best to balance comfort, efficiency, and points cost.
The Reel Avalanche
The inside of my brain while going through every possibility
Leading up to this October 2025 trip, Brian and Whitney had spent literally countless hours on Instagram spamming us with every Japan reel they could find (I admit, I kind of enjoyed them).
Honestly, as the planner, those reels were fun, but also put an immense amount of pressure on me - how could I possibly know which places were actually worth visiting? I may speak Japanese and understand the culture, but I can't read minds.
Our friends are super easygoing, and their food-centric travel style aligns with ours, but this would be their first time in Japan. With so much to see and take in (quite literally), the possibilities were limitless, and I was getting overwhelmed.
Shota’s Happy Place
Full disclosure: I love planning the “bones” of trips. The “bones” are flights, hotels, and routing - the decisions you can’t easily undo once you land. I love the challenge of finding award flights, exploring multiple city routing options, and booking award nights that suit the specific dates & places.
But after all the flights and hotels are booked, I usually hit a state of happiness - Shota’s Happy Place - maybe, and I just kind of move on to the next award trip, even if it’s hypothetical. (Cory hates this - she always tells me to enjoy the moment instead of always planning the next thing. She may have a point, pun intended.)
I literally planned and booked three entire itineraries during Covid when we couldn't travel to Japan - more on that in a future post - only to dismantle it entirely months later when Covid raged on.
So with so much focus on how to keep our friends happy and excited in Japan, I was going crazy researching the “meat” of the trip - the restaurants we wanted to reserve, the cool bars, the matcha farm tours, the endless cafes and hole-in-the-walls - my brain was busting by the seams.
Leave Space for Japan to Surprise You
Now you understand why I only touch some of these “meaty” things.
I mostly care about getting the bigger things right, and then exploring the cities and areas organically and authentically - you know, not planning too much so you have time to stumble on something no one has ever blogged or made a reel about.
Those moments, though rare at times, are gold - and those memories stay with you forever.
Like this really random “rubber-ducky” cafe which turned out to be really really good. Apparently there are 3 hidden ducks that are not yellow or orange and if you find one, you get something special… We opened a few drawers but it was mind boggling how rubber-ducky infested this cafe was! The mascarpone ice cream + berry pancake is very much alive in my food dreams though
Time to Focus on the Points
With the bones in place and priorities set, it was time to put those points to work - starting with getting our friends to Japan rested, comfortable, and excited.
Part 2 will explore Conrad Tokyo, how to (not) deal with jet-lag, and my recommendations for starting your trip the right way - by telling you what went the wrong way.
