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Last month, I took a trip to Asia that involved hopping around the continent, coordinating dates with friends and family, and making a few last-minute pivots along the way. I thought it would be fun to report on what I booked, but also use this as a way to demonstrate the power of miles and points — and honestly, just how many places you can go.
The Context
A few things needed to line up:
- I had a voucher for Tao Philippines due to a last-minute cancellation of a non-refundable expedition from 2025
- My partner is studying in a PhD program in Miami and Spring Break in March is one of the few guaranteed holidays (March 9-13)
- Having travelled Japan together multiple times, the goal this time would be Taiwan
- My high school-aged younger brother has a one-week March Break (March 16-20)
- Japan’s been on his bucket list for years
- A friend — who rarely travels, so this is a special occasion — wanted to travel to Taiwan together
- Due to the above date restrictions, we settled on March 22-29, with a few days in Macau until April 1
- I wanted to catch the cherry blossoms in Japan, typically late March/early April, so I would head back solo after Taiwan
Therefore, I intended to go to the Philippines first to take my 4-day Tao Philippines expedition through the islands of Palawan, then travel with my partner, my brother, and my friend for a few weeks before going to Japan to hopefully catch some blossoms.
The Flights
The Transpacific Crossings
By the time I had everything in place, I had missed the one-year booking window. Given how hard it is to find transpacific premium cabin space these days, I figured last-minute bookings would be my best bet.
For my brother, I ended up booking him on a paid cash ticket outbound in WestJet business class for $1,355 CAD (I got lucky catching this fare) and a return in WestJet economy for 54,500 Flying Blue miles.
As for my partner and me, I set a bunch of alerts on seats.aero.
For the outbound flights to Asia, I received Thrifty Traveler alerts for China Airlines business class space on Phoenix—Taipei (new route by China Airlines) back in October for a series of late February (for me) and March dates (for my partner) that worked perfectly. Phoenix is a 5-hour positioning flight from Miami, but I’m not one to look a gift horse in the mouth. I snapped them up immediately for 72,500 Flying Blue miles (transferred from Amex US MR during a 25% transfer bonus) + $180 CAD per person.
China Airlines A350 business class
On the return leg, I miraculously received a seats.aero alert last July for ANA business class on the Tokyo (HND)–Seattle route for 55,000 Aeroplan points. It was on the Monday after the break ended, but after explaining how rare an opportunity it was and booking it meant not needing to wait until days before departure to hopefully get something better, my partner agreed Monday would be just fine.
As for positioning flights on the departing leg, I bought Fort Lauderdale–Phoenix tickets on JetBlue for 5,200 TrueBlue points (transferred from Chase Ultimate Rewards) + $5.60 USD. My partner purchased a cash ticket on American Airlines from Miami to Phoenix for $160 USD. On the return, I booked Seattle–Miami for 6,000 American AAdvantage miles + $5.60 USD (transferred from RBC Avion).
The only thing missing now was my return from Japan. I wanted to fly either ANA First Class or Japan Airlines A350 First Class, so I set seats.aero alerts and got to work studying award release patterns — stay tuned for next week’s post to see how that turned out.
Intra-Asia Flights
With the most important flights booked, I still needed to book a few intra-Asia flights:
- From Taiwan roundtrip to the Philippines + domestic Philippines flights
- From Taiwan to Japan for my partner and me
- From Japan to Taiwan for me (to meet my friend)
- From Taiwan to Macau (for me)
- From Macau to Japan (for me)
Due to the tight timing of my Tao Expeditions boat, the only Taipei–Manila–Coron and El Nido–Manila–Taipei flights that would work were on a combination of China Airlines, Cebgo, AirSWIFT, and Air Asia. The only one bookable with points was the China Airlines segment, but with no award space and no flexibility, I went ahead and booked everything on Expedia for TD and used TD Rewards earned from my TD First Class Travel Visa Infinite to offset the cost.
Landing in Coron, Philippines
The Japan–Taiwan (stopover)–Macau piece was easily handled with 35,000 Aeroplan points and EVA availability departing from Osaka, which fit my itinerary perfectly. I also got lucky from Macau back to Japan with ANA business class availability on Hong Kong–Tokyo, which I booked for 22,500 Virgin Atlantic points (transferred from Amex US MR during a 40% transfer bonus).
Ironically, I would’ve preferred to book economy tickets to save a few points, but business class was all that was available. Well, if the heavens deem it so, who am I to disagree? 🙂
My goal for Taiwan–Japan was to book Starlux business class for 15,000 Atmos Rewards per person, but it never ended up opening up. Eventually, I got seats.aero alerts for Kaohsiung–Tokyo on China Airlines, which honestly worked even better for our itinerary. Travelling with P2 made a business class splurge feel more justified, so I spent 21,500 Virgin Atlantic points per person and grabbed two seats on CI’s A321neo (featuring lie-flat seats, which was neat).
China Airlines A321neo business class
Last Minute Flight Pivot
As my trip in Asia progressed, it became clear that the cherry blossoms in Japan were blooming earlier than I had anticipated.
Nakameguro in Tokyo
About 10 days before departure, I decided to skip Macau. Cancelling my Aeroplan and Virgin Atlantic tickets was straightforward, albeit with cancellation fees. I opted to cancel my Aeroplan ticket rather than just removing the Macau leg because there was Starlux business class award for Osaka–Taipei, so I grabbed that with 15,000 Atmos Rewards instead (my EVA flight would’ve cost 30,000 Aeroplan points).
My first time on Starlux A330-900neo
Given the situation in the Middle East and passengers being rerouted throughout Asia, on top of the general cherry-blossom-induced high-season availability, booking a new ticket from Taipei back to Japan proved challenging. After what felt like endless searching, I discovered a new route on FlightConnections: Starlux flies Taipei–Kumamoto. What’s in Kumamoto? I’ve never heard of it, but there was Starlux business class space for 15,000 Atmos Rewards points, and that’s all I needed.
I ended up really enjoying Kumamoto
Two days later, I booked a Kumamoto–Tokyo flight on ANA economy for 7,000 ANA Mileage Club miles (transferred from Amex US MR). This flight was not available via Aeroplan or United MileagePlus.
The Hotels
Since the Tao Expeditions trip (I realize I’ve mentioned it several times now, but this is not an ad nor sponsored, although I genuinely enjoyed my trip immensely and recommend it to everyone) covered most of the nights in the Philippines, I only needed one additional night. I chose Cadlao El Nido for $350 CAD through Expedia for TD and offset the cost using TD points at 0.5 cents per point.
4 days of sailing, snorkelling, and beautiful beaches
Taiwan
For the first two nights in Taipei, I booked one night at the Regent Taipei followed by one night at the W Taipei using Amex Fine Hotels + Resorts since my Amex US Business Platinum card comes with a $300 credit twice a year (Jan-June and July-December). There were two reasons for this: the hotel credit is per stay, and, most importantly, I wanted more Marriott elite nights; the first night at the W was exorbitantly priced.
W Taipei
After that, I needed one night in Tainan and booked a night at the Aloft Anping for $135 CAD, including all fees. The points price was reasonable, but cash rates qualify for bonus EQN under the current Marriott promo.
I then spent one night in Alishan, booking the Yin Shan hotel for $360 CAD. Finally, I would spend 3 nights in Kaohsiung and used more Amex FHR credits from my and my partner’s Amex Business Platinum to book three nights at the InterContinental Kaohsiung with a total out-of-pocket cost of $160 USD.
A side quest to Starlux 7-11
When I returned to Taipei later on with my friend, I booked a four-bed private room with private bathroom at the Meander 1948 hostel for $1,375 CAD for 7 nights. This was exactly what we needed, as we’d need 4 beds and ideally would not have to share. The setup was fine, the hostel facilities were great, and I’d easily book it again for a friend group trip.
I love a good Taiwanese breakfast
Japan
The first three nights were in Tokyo, so I booked one night at the Mesm Tokyo with my soon-to-expire 85,000-point Marriott Free Night Award (earned from my Amex US Bonvoy Brilliant card) and two nights at the Courtyard by Marriott Tokyo Ginza Hotel using 35,000-point Marriott Free Night Awards (FNA) (earned from the Amex Bonvoy and the Amex Bonvoy Business cards on both sides of the border) and topping up 10-15,000 points per night.
There was initially no availability, so I had set alerts using rooms.aero (by seats.aero and a Pro subscription includes both).
The view from the balcony at Mesm Tokyo
About a week before arriving, Marriott announced that you can now top up FNAs by up to 25,000 points per night. I seized the opportunity and rebooked two nights at the AC Hotel Tokyo Ginza. The AC and Courtyard are right next to each other, but I’ve yet to stay at the AC, so I wanted to check it out. Ginza is my favourite place to stay in Tokyo, so I’m more than happy to use all my FNAs here (the cash price was about $800 CAD per night).
The next 3 nights were in Kyoto and while I briefly considered spending 45,000 Hyatt points per night at the Park Hyatt Kyoto, I ultimately decided on the Hyatt Place Kyoto for 8,000 points per night (transferred from Chase UR). It was my brother’s first time in Japan, we’d be out exploring most of the day, and the Hyatt Place is centrally located right on top of a subway station.
My favourite hotel in Kyoto is the Ritz-Carlton, but prices during my dates were a whopping 154,000 Bonvoy points per night — a far cry from the 100,000 per night I paid back in November 2022.
Finally, I’d spend 2 nights in Osaka and I redeemed my Hilton Free Night Certificate at the Waldorf Astoria Osaka (earned from my Amex US Hilton Aspire card) when I saw standard room availability. I was keen to check out this newly-opened property, but did not want to redeem 100,000+ Hilton points for the second night as my brother’s flight out was at 8AM. Luckily, I was able to score a discounted rate at the Moxy Osaka Umeda for $110 CAD.
Waldorf Astoria Osaka
Upon returning to Japan solo at the end of my trip, I would have 2 nights in Kumamoto and 2 nights in Tokyo. I booked 2 nights at the REF Kumamoto by Vessel Hotels on Expedia for TD, once again offsetting the entire $250 CAD hotel cost.
Tokyo accommodation was more challenging to book last minute and I initially booked two nights at the 9h nine hours Hamamatsucho (a capsule hotel) for $250 CAD with my TD Rewards points. Then, the first night opened up availability at the Courtyard Ginza, so I grabbed that with my 40,000-point Marriott Free Night Award and topped up 10,000 points.
The FNA was earned as my Annual Choice Benefit for reaching Marriott Titanium Elite and last year was actually my first time selecting it since I usually pick 5 Nightly Upgrade Awards.
Can you believe this cost $125 a night?!
Takeaway
Yeesh. This blog post ended up being quite long, but I hope this shows how you can string together a trip like this to East Asia using miles and points while minimizing out-of-pocket expenses. Of course, all the money I saved went straight to shopping in Japan, but I digress.
Understanding award availability patterns, taking advantage of paid services, and using tools like Flightconnections were all necessary to make this trip happen, including when I had to pivot at the last minute. It’s important to collect transferable currencies to keep all your options open, but also worth considering making a speculative transfer when a bonus is being offered if you are likely to make use of the points on an upcoming trip.
