Flights, Hotels, and the First 48 Hours: When the Plan Meets Reality (Part 3 of 5)
We booked everything perfectly - then the first 48 hours taught us otherwise.
Plan vs Reality: kind of like seeing Mt. Fuji above the clouds - once you land, you don’t see squat
My goal was to get our friends, Brian and Whitney, to Japan rested and ready for their adventure - but maybe they arrived a little too energetic.
Cory and I had actually arrived a few days earlier to visit family, so by the time they took off, we were already in Tokyo.
That changed my mindset completely. I wasn’t just booking flights anymore - I was preparing for their arrival. Would they be wrecked? Hungry? Euphoric? Would premium economy actually take the edge off a 14-hour journey?
I was extra curious because we were planning to fly this exact same route ourselves in 2026. In a way, this was the preview.
When was the last time you got off a 14-hour flight and felt energy? When you were 10? But, before I tell you how my planning paid off - and how things went wrong - let’s get to the point: how did I distribute the miles, and what did we book?
The Plan
With our dates firmed up, I eagerly got to work and quickly found award flights for their departure. It wasn’t easy since we were only a few months away from the trip at this point - I usually book our trips a year to ten months in advance.
Departing from Boston early morning, routing through John F. Kennedy, NY on a 10 AM flight, arriving in Haneda Airport, Japan at 2:35 PM the next day (flight AA167).
Since we couldn’t find Premium Economy or Business class on Japan Airlines (JAL) from Boston to Narita airport using AAdvantage miles we got them the next best thing - using 60,000 American Airlines miles for each person to fly on American’s newest flagship aircraft in premium economy (Boeing 787-9 Dreamliner).
Having them arrive at Haneda was a huge win for me, because I wanted them to be able to grab their bags after immigration and just hop into a taxi to reach the hotel. Narita Airport, on the other hand, can get a bit confusing and stressful if you were to try to navigate the “Limo-Bus” or the NaritaEX/ Skyliner trains on your first visit.
We had them transfer 190,000 Amex points to Hilton, resulting in 380,000 Hilton points (due to the 1:2 transfer ratio).
We could have waited for a transfer bonus from Amex which runs quite often throughout the year (great link here from the Frequent Miler), which would have maybe cost them only 140,000 Amex points to get the 380,000 we needed. But I’m glad we pushed them to act early because not much longer, Hilton devalued some of their top hotels and the Conrad Tokyo - which we booked for 5 nights with “only” 380,000 points quick ballooned to 520,000! It literally jumped from 95,000 a night to 130,000 in a matter of weeks.
(Tip: Hilton and Marriott have a cool feature where you get the 5th night free if you can cover 4 nights using points, so this only set us back 380,000 Hilton points)
An Important Points Lesson
So herein is a small points-world lesson - sometimes it’s best just to use what you have to get what you can while you can, rather than speculatively wait for a “sweeter deal” which may never come - or in this case, become downright bitter.
The Arrival
Our friends literally arrived at Haneda Airport at 2:35 PM and were at the hotel checking in before 4 PM - we spied on them around a corner of the Conrad Tokyo’s grand lobby - slightly jealous of how easy it was for them to get there (had they landed in Narita, they would have arrived around 8 PM). We surprised them when they came around, taking commemorative photos.
This was one of those decisions that paid off within hours of landing.
When we were still planning the hotel, I specifically told Whitney that taking a taxi would be so worth it after a long flight - that it’s a fantastic option to have, since taking a taxi from Narita would easily cost $250, instead of $40. She playfully jostled me, saying that she liked a challenge and wanted to explore Japan’s famous train system.
Ohhhh kayyy.
I reminded her that after a 14-hour+ flight, feeling grimy and in need of a shower, and lugging luggage - navigating Japan’s complex train system is the last thing she needed to do.
Thankfully, in the end, she gave in and took a taxi. The only train exploring she had to do on her own from start to finish was the bullet train back to Yokohama, then to Narita for their flight home, which was apparently enough excitement for her.
Oh, I didn’t mention Brian because he doesn’t really navigate well. It’s not that he can’t - he won't. He’s too chill to care. Not to mention, Brian kept messing up his digital Suica balance (he didn’t load it when we told him to) and kept getting stuck behind the train station exit gates.
I don’t think they would have arrived at the Conrad before 4 PM if they decided to have fun with the train system.
Off to the Best Start Imaginable!
Into the night we go!
By 5 PM, they were all freshened up and ready for dinner. Cory and I were stunned because, on our first evening, we usually shower, soak in the tub, and get a room order for the night. We knew our friends lead Energizer Bunny lives and were crazy active, but wow - we’d never seen anything like it!
So off we went to grab some Japanese BBQ, which was an instant hit. As we finished our last sips of draft beer, Whitney whipped her phone out, and with a slick smile, showed us our next stop: a British-themed bar she’d found in a reel. At this point, nothing surprised us.
Too Smooth it Makes You Wonder
After a wonderful first night out, Cory and I were 90% convinced that our friends were just built differently. I played a lot of sports growing up, and that is most definitely a real thing: some humans are just special - they aren’t like the rest.
And so we figured that our super-human, circadian-rhythm-buster friends could truly handle this time-change business without batting an eye.
The Terrible Signs Begin
The next day, even before we enjoyed a generous breakfast spread at the Conrad, our friends had already worked out and enjoyed the spa steam room. Brian showed up to breakfast in his slides, which threw Cory off, until she realized they had just come straight from the spa. No shame there.
After breakfast, we visited Glitch Coffee in Ginza, found a local unajyu shop (grilled eel), shopped around, had a couple drinks at a mysterious lab-bar - and we were even able to squeeze in a little down-time back at the hotel in the late afternoon.
Then. The troubles began.
I had very stupidly booked an omakase style dinner. I did so based on our friend’s insistence on how they don’t ever suffer from jet-lag and how they love all things Japanese.
Well, even their love for Japanese omakase couldn’t overcome their nausea as their stomachs caused an internal, gut-wrenching rebellion that just wouldn’t go away.
Cory and I usually don’t make dinner plans or reserve anything in the evenings for this very reason. We usually don’t experience too much jet-lag in terms of sleepiness or lethargy, but we do feel like our stomachs are upside-down on our first few nights.
Breakfast and lunch go great, and dinner is almost non-existent.
Here we were walking with our wobbly friends, smiles completely wiped off their faces, looking like they could gag at any moment.
As we sat down, Brian confessed that he hadn’t been feeling great since the drinks in the afternoon, and we nearly blurted out, well, duh! but held it together as large portions of sushi and handrolls came barreling onto our small table.
Long story short, they were eventually able to feel a bit better and ate most of what was served. But we were across the table from them, dying internally the entire time, realizing how torturous it is to swallow down food when your stomach is turned off.
So whose fault was it? Absolutely mine. Since I outdid myself with getting them to the hotel so smoothly the first night, I think it gave our friends false energy. Thereafter, Cory and I completely believed that they were not human, and thought their stomachs were also extraterrestrial.
Alas, it was not meant to be.
A Tip for Your Stomachs
So a big learning moment for all you future jet-laggers: do not book a dinner reservation for the first few nights if you want to save yourself from nausea and embarrassment.
I only say embarrassment because on our first trip to Japan, we also suffered from “jet-lag stomach” and had to give up on a platter of expertly prepared sushi.
We had the two platters plus some extras that were quite hefty and rich. Instant regret.
The whole meal became a mental calculation: I only have space for two more pieces - if I don’t eat that o-toro piece that cost $10, I’m going to puke mentally - so I might as well risk it and eat it while I can.
Definitely not the kind of mental negotiation you want to have between your pride, stomach, and wallet.
In the End, it was All Good
But of course it wasn’t all doom and gloom for our friends. The next day, they worked out and enjoyed the spa in the morning - claiming that it helped them to sleep better, and lighten the blow of jet-lag.
With mornings being the best time of day for most people with jet-lag (from the U.S.), having a healthy spread of fresh juices, hearty options, and Japanese and Western food was a huge boost.
A brief shout-out to Conrad Tokyo: they have a really well maintained and therapeutic steam room, which we all took ample advantage of both at the start and end of each day of Tokyo adventure.
Later in the trip, we almost had to pay nearly $200 per person to use the spa, and another hotel, The Ritz-Carlton Osaka of all places, had parts of the spa area closed for routine maintenance, which was a blow to our sauna-ful Japan trip.
Next, in Part 4, we check into a brand new Osaka hotel - where a surprisingly tense check-in turned into one of the most memorable hotel experiences we’ve ever had.
