A few weeks ago, my boyfriend casually mentioned, "Oh yeah, I think we might tour in Japan next year." (He's a drummer in not one but three bands.)
He's the kind of guy that offhandedly mentions BIG THINGS in the same way that other people mention what they're considering for lunch. But I know the other people in this band. They don't make idle threats. If they say they're going to Japan, they're going to Japan.
My brain immediately went into overdrive, searching flights and planning a whole damn trip in my head at 11 pm. Japan is – and has always been – a bucket list trip for me.
Then April dropped this challenge a few weeks later, and it seemed like fate. This trip (with these challenging dates) is an imaginary trip, but two people to Japan from the East Coast is something I may be booking very soon.
Final tally: 200,000 points and $1,393. Every single point, six nights, three cities.
Two things I want on the table before we start, because I'd rather you hear them from me:
One: I got here by driving to Canada. My assignment said East Coast. It did not say which country. 🫣
Two: 70,000 of my 200,000 points came out of Rove Miles, which is not a credit card program. The rules didn't say I couldn't, so I did, and I'll defend it below. But if you don't have a Rove balance, this exact trip isn't sitting there waiting for you.
So let's get into it.
First, the ground rules
Quick refresher on the challenge: two travelers, departing the East Coast, and the whole trip has to fit inside a fixed window over Thanksgiving week. The budget is 200,000 points and $2,000, and the points come from a maximum of three cards.
Mine: Rove Miles for the outbound, the Capital One Venture Rewards Credit Card for the transfer to Cathay, and my Chase Sapphire Reserve® doing most of the actual paying.
Here's the itinerary:
Nov 21: Toronto (YYZ) → Tokyo Narita (NRT) on WestJet, booked through Qantas (70,000 Rove Miles + $160 for two)
Nov 22–25: Three nights at the Hyatt Regency Tokyo Bay (45,000 World of Hyatt points)
Nov 25: Tokyo → Kyoto on the Shinkansen ($139 for two)
Nov 25–27: Two nights in a Kyoto ryokan ($429)
Nov 27: Kyoto → Shin-Osaka, all of 13 minutes ($38 for two)
Nov 27: One night at Caption by Hyatt Namba Osaka (15,000 points)
Nov 28: Osaka (KIX) → Toronto (YYZ) on Cathay Pacific (70,000 points + $627)
Let's go through it.
Getting there: Qantas saves the day
About those dates. This was hard and took up the bulk of my trip planning.
Here's just a sample of what I searched:
Option 1: Alaska Airlines
I looked at all major East Coast airports on Alaska to see where I could find the best availability. You can see how wildly pricing fluctuated depending on day: 👇
Those 37,500-mile options on the following days? Truly terrible itineraries. Like, two days to get there with overnight layovers terrible. And spending 125,000 on two tickets there didn't give me enough to work with for the way back.
Option 2: Japan Airlines
Tried to check JAL. I hadn't booked an award ticket with them before, so I just signed up for a frequent flyer account during my search process.
Access denied. 👇
And this is why we always recommend setting up all your frequent flyer accounts in advance of needing them.
Fail.
Option 3: Aeroplan
After hours of searching (there were many other options entertained that I'm not even sharing here), I was starting to lose hope.
But then I started thinking outside the box.
My starting destination was from the East Coast. Not specified which country in North America. As I've recently learned, YYZ is our most searched departure airport in Daily Drop Pro. Plus, living in Buffalo, Toronto is basically our secondary airport. Plenty of people drive the two hours to Toronto to get cheaper, direct flights to their final destination.
Imho, Toronto was fair game.
The Aeroplan options started to give me some hope, until I looked at the overnight layover in Montreal. 💀 👇
If this was the best I could do, I could make that work. The mileage and fees were low, even if the itinerary wasn't great.
Option 4: Qantas
I kept going in the same vein. I learned my lesson from the Points Pursuit challenge – get real creative.
The rules for this challenge didn't say anything about using programs outside of credit card programs, so I leaned on the 50% bonus from Rove to Qantas to celebrate the launch of their partnership. 👇
I ran a search and I immediately thought, "I'M SAVED": 👇
With the 50% transfer bonus, that's just 70,000 and $160 for two. Hallelujah.
Three nights in Tokyo
Moving onto the fun part: accommodation.
Hyatt has a ton of properties in Japan, and luckily I had enough points left to book one for three nights in Tokyo upon arrival: 👇
45,000 points for three nights works out to 15,000 a night, which for Thanksgiving week in Tokyo I will absolutely take.
Getting in at 3:30 pm on Sunday means that that day is a crash out day anyway. And for a major city like Tokyo, two days is the bare minimum imho.
Fair warning, and I'd rather say it than have you find out on arrival: Tokyo Bay is not central Tokyo. It's out by the water near Tokyo Disneyland, and you'll be on a train to get anywhere you actually came to see. Unfortunately, I didn’t have the points balance to stay anywhere closer, but if you do, there are plenty of other options (or you can of course pay cash). 🤷♀️
Tokyo to Kyoto, and a fight with a website
Next up: Kyoto via the Shinkansen, or high-speed train.
The official Shinkansen is something else y'all. I fought with it for at least an hour before it was finally wrangled into submission. I mean…what website has after hours???
I can see why there are numerous travel agencies that have sprung up, selling tickets online via functional and friendly websites (for a not insignificant upcharge, of course).
But, the beast finally tamed, I was able to see pricing for my route: Tokyo to Kyoto. 👇
As of writing, the exchange rate for 22,200 JPY was around $139 USD.
Keep in mind that there are rail passes that might make sense if you're staying longer, but for this trip, buying individual tickets was the most economical option.
Two nights in a ryokan
Kyoto is the historic former Japanese capital, and as such, I wanted the full traditional experience.
Give me a ryokan (Japanese inn) with tatami floors, futons on the floor, and gentle hospitality. I'm sure that's not for everyone, but this is my trip, and I'll stay in a ryokan if I want to. 🤷♀️
I like to mix up the accommodation on my trips by redeeming some nights for points, and other nights for unique experiences that I could only get in that place. Isn't that why we travel, after all? Or is that just my anthropology background – always desiring a deep cultural dive – showing?
I found the following ryokan on Chase Travel℠ - another lesson from Points Pursuit. Book hotels there for the 8x multiplier earned with my Sapphire Reserve. 👇
Two nights, $429, and it had it all. There was even a private onsen for guests to book.
Yes please.
One night in Osaka
The trip coming to an end, it's time for the final night in Osaka.
It's just a 13-minute train ride away from Kyoto: 👇
$38 for the two of us, which after the Shinkansen booking experience felt like the system apologizing.
And because I still had some points left, I was able to book yet another Hyatt property for the last night: 👇
15,000 points, and it puts us in Namba for our last night, which is where I'd want to be anyway.
Getting home on Cathay Pacific
Once again, the flights were a bear.
I went through the same barrage of airlines listed above, with flight prices once again ranging wildly. In one instance, one day was 175k, the next was 42,500.
Qantas, which saved me on the way there, was absolute TRASH on the way back.
Finally, I landed on my savior, Cathay Pacific: 👇
A perfectly respectable flight (even if fees were a bit high), made even better by the current 10% transfer bonus.
Here's the honest accounting on that one: 76,000 Cathay points, which cost me 70,000 Capital One miles after the bonus, plus $627 in fees. That's the single most expensive line in this entire trip, cash and points both.
Would I rather have paid $160 like I did on the way over? Obviously. But this is what the last week of November does to a return flight, and I'd rather show you the number than quietly leave it out. 😮💨
The damage
Adding it all up:
Points: 70,000 (Rove → Qantas) + 45,000 (Hyatt, Tokyo) + 15,000 (Hyatt, Osaka) + 70,000 (Capital One → Cathay) = 200,000
Cash: $160 (outbound) + $139 (Shinkansen) + $429 (ryokan) + $38 (Osaka train) + $627 (return) = $1,393
Every single point spent, $607 of the cash budget left over, and six nights across three cities.
What I'd actually do (if I weren't locked into these dates)
Set up the JAL account six months ago. That 60-day waiting period cost me an entire option, and I've been telling readers to do this for a year. Do as I say, not as I did. 🫣
Move one day. One of my searches showed 175,000 points and 42,500 points on consecutive days. If your dates are flexible at all, you can save a tonnnnn of points.
Buy a rail pass. Individual tickets won this time because we were only making two train trips. Add a third city and the pass starts paying for itself.
Don't count on the Rove bonus. The 50% transfer promo was live when I booked and it's the reason my outbound was 70,000 instead of 103,600. Transfer bonuses expire. If it's gone when you read this, price the Aeroplan option with the Montreal layover instead and decide how you feel about an overnight in Quebec.
The bottom line
Can two people get from the East Coast to Japan and back over Thanksgiving week, plus six nights in Tokyo, Kyoto, and Osaka, on 200,000 points and $1,393?
Yes. Barely, and only because I was willing to drive to another country and dip into a program that isn't a credit card.
That's the part I'd want you to take from this rather than any specific booking. The itinerary that finally worked wasn't the fifth version of the same search. It was the version where I changed one of the things I'd assumed was fixed.
For me, that thing was the departure airport.
For you it might be the dates, or the airline, or which city you fly home from. But if you've run the same search four times and hated the answer four times, the search isn't the problem. 🤝
And if you're nowhere near a second airport and Japan is nowhere near your list, the Buffalo-to-Toronto trick still works for basically anywhere else. Go see what's cheap from the airport you've been ignoring.
