First Class Family Trip to Japan

JAL First, Starlux, EVA, Ritz Carlton, and Conrads

by Sash
a map of the world

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Our family’s annual March getaway is just around the corner, and we are so excited to spend a couple of weeks in Japan to take in the sights, sounds, and, of course, the cuisine. Planning a family trip is always challenging when booking flight awards, let alone in first-class for an entire family. Top that off with exquisite hotel award redemptions, and you have a combination that maximizes the points inventory.

I’ll be sharing not only what I’ve booked in terms of flights (JAL First, Starlux, EVA) and hotels (Conrad, Ritz Carlton, Luxury Collection) but also how I booked them using points and miles while ensuring maximum redemption value to the best extent possible.

Flight Planning

Let’s first take a look at the flights I booked. This took the better part of a full year to finalize. This is because I often book the award flights I find ~10 months out and adjust as better flights become available. This could mean paying a nominal change/cancellation fee, but I have no qualms about this: it is a small price to pay to secure the best flights especially since my travel dates are fixed.

I’ll provide an overview of all the flights I booked for the first class family trip to Japan, including tips that may help you if you’re looking to book something similar.

Flights – Air Canada Business Class

Montreal (YUL) – Dallas (DFW)
27,800 Aeroplan + $111.33 taxes

  • This flight was booked approximately T-6 weeks out at an Economy Latitude fare and e-upgraded
  • The Aeroplan points were earned through a plethora of credit cards (too many to list)
  • Air Canada status to upgrade was achieved by holding the Chase Aeroplan credit card and a status extension from Air Canada for my 50k status.
a seat in an airplane

Air Canada A220 Business Class

Flights – Japan Airlines First Class

Dallas (DFW) – Tokyo (HND)
80,000 AAdvantage + $5.60 taxes

  • Booked just weeks before departure.
  • Points earned by transferring from RBC Avion, which were earned from the various RBC credit cards available in Canada. Avion transfers to AAdvantage at a rate of 1:0.7. Note that RBC sends to AAdvantage every Thursday night; transfers are not instant.
  • If you want to fly JAL, here are some tips:
  • British Airways Avios has access to JAL award flights at the end of the calendar before AAdvantage and Alaska, albeit at a higher cost in points and taxes. Only 1 seat is released at this time, and this is subject to change.
  • JAL First release patterns are ever-changing, but the patterns stay constant for a period before changing again. What this pattern is an exercise for you to figure out. 🙂
  • Awards are released at different times for each city pair.
  • Award seats will only be released close in if unsold seats exist (Fx, where x > 0).
  • Award tickets are such high in demand that seats are booked within 1-2 minutes of release. Some programs can have access to seats minutes before others.
  • The new JAL A350-1000 First Class (and business) class cannot be booked through the conventional AAdvantage, Alaska, Avios methods.
  • Check out more JAL First hints on a What Did You Book? – Atlantis Paradise Island and Top 3 Flight Bookings
a seat and table in an airplane

Japan Airlines First Class

Flights – Starlux A350 Business Class

Osaka (KIX) – Taipei (TPE)
15,000 Alaska Mileage + $41.60 taxes

  • Booked in September 2023 (T-6 months out) when Starlux awards became available through Alaska
  • Points earned from the legacy Canadian Alaska Airlines credit cards, Marriott Bonvoy Transfers, Point purchases, and other “fabrication” methods.
a row of seats in a plane

Starlux A350 Business Class, source: Business Insider

Flights – EVA Air Business Class

Taipei (TPE) – Toronto (YYZ) – Ottawa (YOW)
88,200 Aeroplan (Flex) + $91 taxes

  • Booked May 2023 (T-10 months out) when EVA Air released a plethora of seats through Aeroplan.
  • Aeroplan’s dynamic pricing through the Toronto-Ottawa route worked in my favour, effectively lowering the price to less than a Taipei-Toronto flight.
a seat in a plane

EVA Air 777 Business Class, source:

Flights – Takeaway

As we move further past the COVID-19 era of flight award abundance, I hear more of folks having trouble finding award space. Social media has further fueled this, with influencers flexing their fancy flights without detailing how they were booked. I hope this flight planning exercise for a family of 3 to Japan will inspire others to not give up and continue the hunt for flights they aspire to take.

What are 3 key takeaways from what I’ve written thus far?

  1. Have your points diversified in different award programs and/or in transferrable currencies like American Express Membership points or RBC Avion.
  2. Study award release patterns, use tools, stay up to date on large award seat releases, and, most importantly, be involved in points and miles communities.
  3. If you can’t do #2, consider hiring a travel consultant (not me!), but remember that no one can do a better job than you if you really want something.

Hotels Planning

I was blown away by the astronomical costs of the hotels in Japan ($800+/night). Prices have skyrocketed so much in the post-COVID era that it has become hard to justify spending cash over points at many properties.  In fact, I booked all but 3 nights of my entire 16 day vacation on points, which I rarely do.  Let’s dive right in.

Hotels – Grand Hyatt DFW

$247 (1 night at a negotiated rate)

  • The Grand Hyatt DFW is the only property connected directly to the terminal building, which felt like an excellent option given our late-night arrival and mid-morning flight.
  • A Guest of Honor (GoH) was applied to the booking, which will entitle me to full Hyatt Globalist Status Benefitsa large building with many cars and a freeway

Hotels – Conrad Tokyo

380,000 Hilton Honors Points (5 nights)

  • With the best cash rates at over USD 700+ per night, using 380,000 points was the better incentive, especially with the 5th night free when you redeem 4 free nights.
  • Hilton Points were acquired through the plethora of US Amex credit cards
  • I booked the hotel approximately T-6 months out when there was excellent award availability. However, when I checked award availability T-1 month, the hotel had no revenue or award space available. Book early, especially for an extended staya river with a body of water and buildings in the background

Hotels – Hakone Kowakien TEN-YU

USD 568 (1 night)

  • This is an all-inclusive Ryokan with a private Onsen in each room. It is located in the beautiful mountainous region of Hakone.
  • I booked through Citi Travel using my Citi Premier card, which gave me a $100 travel credit in addition to 10x points earned.
  • In the Hakone region, Ryokans MUST be booked weeks, if not months in advance. This property was sold out 3 months before my arrival.a collage of a hotel and a pool

Hotels – Ritz Carlton Kyoto

3,000 Bonvoy points/night + 2 x Free Night Award Certificates (2 nights)

  • It’s well known that the Ritz Carlton Kyoto is a top redemption in the Marriott Bonvoy portfolio with cash rates north of $1800/night, especially if you have a free night award (FNA) certificate valued at 85,000, which I’ve acquired from my US Amex Brilliant credit card.
  • Certain US Amex cards ran a promo in the late fall of 2023 to acquire an additional FNA after spending $4000. This is how I ended up with 2 x 85,000 FNAs. This effectively saved me 170,000 Bonvoy points.
  • I utilized hotel award alert websites to stay informed of fluctuating rates and secured the lowest amount over 85,000. This exercise resulted in several reservations, cancellations, and rebookings. It’s just how you beat the Bonvoy at its own game.
  • Award availability was excellent up until T-7 days.a collage of a hotel

Hotels – Hotel The Mitsui Kyoto

130,000 Bonvoy Points + 2 x Free Night Award Certificates (3 nights)

  • Another top redemption property as part of the Marriott’s Luxury Collection portfolio with rates once again north of USD 1000+/night
  • The cost breakdown was 2 x FNA with a 13,000 top-up per night as the rate was 98,000 per night. The 3rd night was straight points at 104,000.
  • I used my wife’s FNAs, which she acquired from her US Amex Bonvoy Brilliant credit card and the additional FNA she acquired from the Fall 2023 promo.
  • Award availability was excellent up until T-7 a collage of different buildings

Hotels – Conrad Osaka

2 Free Night Awards (2 nights)

  • This property was booked using 2 x Hilton Free Night Awards acquired from my US Hilton Aspire and Surpass credit cards. The point equivalent value was 95,000, and the cash rate was approximately ~USD 650. While this is not an optimal use of an FNA, I’m happy with it, given that the FNAs are expiring soon.
  • Award availability was quite good up to T-30 days.a collage of a room with a view of a city

Hotels – W Taipei

$227 (1 night at a negotiated rate + extra 20% off)

  • This property was chosen based on positive feedback from many people.
  • I would receive an effective 20% discount by utilizing the Bonvoy Gift Cards that I regularly purchase when they come on sale at a 20% discount through American Express offers. a collage of a hotel room

Final Word

A two-week first-class family trip to Japan is challenging to accomplish on points and miles, even for the seasoned points guru. Inflated hotel costs in Japan, combined with scarce transpacific award space in premium cabins, have frustrated many folks. However, it’s not impossible with the right strategic approach, and I’ve tried to demonstrate this so that it may help others reach their travel goals.


Robert Covington p March 14, 2024 - 12:53 am

I think business class award for YYZ-TPE on aeroplan is 75K, you mentioned you paid 88.2K, I’m trying to figure out how did dynamic price work in your favour, unless I missed something, please let me know, thanks for many used tips, thumbs 👍

Sash March 14, 2024 - 10:23 am

Hi Robert. YYZ-TPE is just over the 7500 threshold so the fare is 87,500 on business low fare

Anthony March 12, 2024 - 12:00 pm

Great post Sash !!

You mentioned using British Airways to find availability on JAL 1st since BA’s calendar extends longer.

Can I use that calendar to find availability But then call Alaska Miles call center to book the flight Even though it doesn’t show on alaska’s calendar of availability, to save on the taxes ?

Thank you.

Sash March 14, 2024 - 10:12 am

Hi Anthony. No, you cannot call Alaska to book an award beyond its calendar window. Agens don’t have any more access than what you see on the website.


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