The Framework I Use to Plan Every Japan Trip With Points - The Complete Overview
How I search, compare, and strategically book award flights and hotels to Japan
The Japan Withdrawal Is Real
If you get chronic symptoms of Japan-withdrawl like I do, the question that dominates your mind is when can I get back to Japan?
I don’t blame you.
Without fail, every time I get back from a trip to Japan, I have Japan-sickness for weeks, if not months.
It’s not that I don’t enjoy my life here in the States - we live in a peaceful suburban area with decent access to Boston, should we crave a little more excitement.
But we don’t go to Boston like it’s Tokyo.
If Tokyo were only 45 minutes away, we would be there literally every weekend. And Tokyo isn’t even my favorite city in Japan!
It’s beautiful when you can find a peaceful abode in a mega-metropolis
The Cure: Planning the Next Trip
Anyways, let’s get to the cure - the fix. How do I plan out our trips to Japan?
My favorite seasons to visit Japan are spring (March - late May) and fall (October to early December).
Although we’ve done winter and summer before, if we could choose, we wouldn’t do it too often.
Part of what makes Japan so fun for us is how it’s so walkable - we just don’t do that enough in the States. And when the weather is too hot, too cold, or too rainy, it literally puts a damper on our trip.
How This Guide Works
Over time, I’ve developed a simple framework for planning our Japan trips using points. Most of the points we use come from a long-term strategy of credit card bonuses and rewards.
This article is the complete overview of that system.
Each step connects to a deeper guide if you want to explore further:
If you follow these steps in order, planning a Japan trip becomes surprisingly manageable.
The Search Begins: Flights First
With the spring and fall months in mind, I use award search tools to find potential dates.
I scribble a bunch of possible departure dates and scour the search engine for the return.
Usually, I start by looking for business-class awards, but I realize they aren’t always available, especially on specific routes. If I find one, great; if not, I move on to premium-economy seats, which are much easier to find (especially direct flights).
From Hotel-Hopping to Staying Put
Once I confirm the flights, I create a calendar in a Google Doc and map out arrival times, transit windows, and hotel stays for each city.
I use an award search tool to see what’s actually possible.
I used to splurge on high-end hotels, staying just one night at a time and hopping from one to the next.
Fun? Yes. Relaxing? Not really.
As I got more trips under my belt (and calmed down a bit), I shifted to booking three to five nights at the same property — giving myself time to enjoy the hotel and absorb its surroundings.
As you’ll see in my trip reviews, avoiding constant check-ins and check-outs removed a surprising amount of stress.
Why Proximity Beats Luxury on Night One
Since most of our flights land at either Narita or Haneda, I often prioritize proximity to the airport over luxury stays from the start (plus, what if there’s a delay and you don’t make it to your first night?
From Boston, a direct flight to Narita airport involves getting to the airport, going through security, and waiting for a 14-hour+ flight.
Then, after the lower half of your body goes numb (in economy - yes I’ve done it many times!) your neck aches and refuses to turn, and you feel like you are carrying the grime of the world (you probably are), the last thing you want is to have to deplane, go through the snakey immigration line, find your baggage, go through customs… and have another 2 hour bus ride to Tokyo.
I’ve definitely done it - many times.
But even with a really nice hotel waiting for you, the idea of going through all of that kills me.
On recent trips, I’ve made a conscious effort to land at Haneda, even though there aren’t any direct flights there from Boston.
This has often allowed us to deplane and reach the hotel in under 3 hours, rather than 4 to 6.
On our return flights, I have no preference, since we are often well-rested and have plenty of time to get to the airport for a 5 PM or 6 PM departure.
Here’s how the trip currently fits together, with confirmed bookings locked in and a few fun decisions still up in the air.
A Sample Itinerary: August–September 2026
Outbound Flight
American Airlines Premium Economy (Flagship)
JFK 10:40 AM → HND 2:00 PM
Booked with Cory’s Alaska miles – 100K + $37.86
Days 1–2: Tokyo (2 Nights)
Super excited to revisit — it’s been over a decade since our last stay.
Park Hyatt Tokyo
70K Hyatt points (Shota)
3-day cancellation window
Days 3–7: Sendai (5 Nights)
Family time.
The Westin Sendai
157K Marriott points (Shota)
Corner Suite Upgrade using Nightly Upgrade Awards
(earned from 50 nights in 2025)
Day 8: To Kansai
No trip feels complete for us without time in this region.
Flight or train — not booked yet.
Most likely via Amex or Chase travel portal.
Days 8–12: Osaka / Kyoto (5 Nights – TBD)
New and exciting hotel options vs. tried-and-true.
Options:
DoubleTree by Hilton Kyoto Higashiyama – 160K for 5 nights + breakfast
Conrad Osaka or InterContinental Osaka – FHR, $300 credit per night + ~20K Amex to cover the gap
Sowaka – 150K per night or Hilton Free Night Certificate
A decision I’m still happily weighing.
Days 13–14: Mount Fuji Area (2 Nights)
We’re going for it. Again.
Will we go 4-for-4 with clear views, or lose to fog?
Fuji Speedway Hotel – FHR credits
Free breakfast, onsen access, $100 property credit
1-day cancellation
Day 15: Yokohama (1 Night)
The obligatory buffer night that nudges us closer to the airport.
Either The Kahala Hotel & Resort Yokohama
or InterContinental Yokohama Pier 8 (~50K IHG)
Day 16: Return Flight
Sometimes comfort beats multi-stop routes in business.
Japan Airlines Premium Economy
NRT → BOS
Booked with Cory’s AA miles – 100K + $89.06
What’s Different
My first step with this trip was to search for flights out of NYC, which was a fun change.
We would be in NY in August anyway, and figured it would be great to take a direct flight to Haneda.
In fact, the very flight we booked is the one our friends flew on during our 2025 trip together. With the seats being the new flagship-model premium economy, we are excited to see how they compare to JAL or ANA.
Proximity and Luxury - a Dream Start to Any Trip
Knowing we’d land in Haneda around 2 PM helped me to book our first two nights in Tokyo at the Park Hyatt.
I’m genuinely excited to be back at this hotel after its year-long renovation and hope to write an in-depth review - more than a decade after our first visit.
At first, I looked at options near Narita since Boston has direct flights there. The Hyatt Regency Tokyo Bay, for example, offers club rooms and suites for 14k–23k points - a fraction of the 45k–70k+ rates you’ll see closer to central Tokyo.
Even so, Haneda offers more direct access to the heart of Tokyo and a much more premium hotel right from the start, which is the best of both worlds!
Sendai: The Closest Thing to Home in Japan
Whenever I’d visit Japan growing up, we would go to the northern city of Sendai, in Miyagi prefecture.
My grandparents and my older brother’s family are there, and it is my home away from home.
I’ve only recently started seeing foreign visitors in the city, but it is a hidden gem, full of amazing food, people, and shopping.
I understand that's a very broad assessment, and you’re not wrong.
It would be hard not to find those things anywhere in Japan, but what sets Sendai apart for me is the fact that it’s cozy - everything is walkable and accessible.
It isn’t as overwhelming as Tokyo, as noisy as Osaka, or as busy as Kyoto. It’s just right.
If you ever get a chance to stretch your legs north, I highly recommend spending a few nights near the station to get a taste.
Small City Problem: Not as Many Options
Sendai included, most smaller cities in Japan don’t have many Western hotels.
As such, using points for hotel nights becomes less rewarding or difficult altogether.
Thankfully, Sendai has two Western options, including The Westin Sendai.
Personally, I am excited to stay there again, with a possible suite upgrade, because similar rooms in the area cost $300-$450 a night, even though the city is overall much cheaper than Tokyo.
Since my brother and his family live near Sendai Station, this hotel is perfect for our stay.
The next best option is undoubtedly the Metropolitan Sendai East and Metropolitan Sendai Station hotels (both built into the station for seamless access), but the stay would have to be paid for in cash rather than points.
I’ve redeemed Chase Ultimate Rewards points by booking through their travel portal, but you usually don't get outsized redemption value for using your points the “easy” way, and it may be wise to save your points for a smarter transfer.
Osaka & Kyoto: Too Many Good Options
Although we have to stretch north to visit family (usually Sendai and Sapporo), we always make trips to the Osaka & Kyoto area to get our fix for some of the best hotels.
This time, I am undecided: I have eight $300 annual vouchers from Amex's Fine Hotels and Resorts (FHR) program, and I’m wondering whether to use them here.
The two hotels I listed are ones we’ve stayed at before and would love to stay at again, with all the perks of an FHR booking (early check-in, late 4 PM checkout, upgraded room, free breakfast, $100 voucher to use, and more).
Conversely, a property like the DoubleTree by Hilton Kyoto Higashiyama or other Hilton properties that we’ve never visited would be a great experience, as we’ve heard great things about how they are not just any “Hilton” or “Double Tree” you’d see in the States.
The final option I’m toying with is the Sowaka Hotel, a beautiful Small Luxury Hotels (SLH) boutique with stunning rooms and a strong commitment to Kyoto architecture and Japanese quiet luxury.
I had 5 nights booked there a year ago, soon after they first joined Hilton on February 7th, 2024.
The award night stays have ballooned from 95k to 150k/ night, sadly following recent Hilton devaluations, but standard rooms seem to be available for a Hilton free-night award if you have the Hilton Honors American Express Aspire card.
Taking a Calculated Risk on Mount Fuji
I’ve often debated whether I should return to the Fuji-Kawaguchiko area.
So far, we are 2 for 2 in seeing the breathtaking mountain in person, but we realize some have struck out time and again because of thick fog. I used to think, it’s just a mountain, how special can it be?
But oh boy was I wrong.
That photo is from 2016, when iPhone cameras were nothing like they are today. It doesn’t do it justice, but imagine waking up to that view after not seeing a thing the first day.
So yes, it’s 100% worth it if you can see it.
For 2026, we are going to take another leap of faith and stay at the Fuji Speedway Hotel using Amex FHR credits.
The hotel is a touch remote, but everything near Mount Fuji is remote, so we’ve come to accept that fate.
What drew me to this hotel was the views from its private onsens. They seem to have indoor and outdoor options, and visitors are raving about the views and the food.
I didn’t need much more convincing after that!
Ending the Trip the Easy Way Home
After one final night somewhere in Yokohama (I call it Little Tokyo), we will take the direct flight back to Boston on Japan Airlines' premium economy.
One quick note is that these seats are in a shell - meaning you slide forward into your own space, and you never bother the person behind you since you don’t recline into their space.
I appreciate that feature a lot as I am very self-conscious about when and how much to recline - I almost never get to lean it back fully, defeating the purpose of any advertised “seat pitch.”
As a tiny little tip (you may not care at all, and that’s ok), for products like the newest American Airlines premium economy seats, even though they lean back into your neighbor's space, if you book last-row seats, you will not have to worry about anything.
The incredible view from above 40 stories
Why This System Works for Us
All in all, this 2026 trip only took me a couple of hours to figure out and piece together.
With all the preliminary research out of the way and my dates firmed up, the only things left to book are relatively low-stress.
I may switch out a hotel or two by the time we actually travel, but that too is what makes award travel so flexible and fun.
What’s Next
I hope this glimpse into my travel-planner brain was helpful - and that the three deep dives below make planning your own award trip a whole lot easier.
Next: The Framework I Use to Plan Every Japan Trip With Points - Part 1: Flights
Also in this series:
The Framework I Use to Plan Every Japan Trip With Points - Part 2: Hotels
