How I Plan to Tackle Award Flights from Florida to Japan via Hawaii (for Seven People!)

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A few weeks ago I published a post on the evolution of my 2020 Hawaii plan into something way more complicated. This is the story of my life… Whether the trip will actually materialize remains to be seen, but  for now I will be operating with the assumption that it will.

If everything goes according to the plan, this is what the map of our adventures will look like:

Maps generated by the Great Circle Mapper – copyright © Karl L. Swartz.

My goal, as always, is to reduce the cash outlay as much as possible. When tackling a complicated family trip with multiple flights, I don’t worry about lodging until the airfare is taken care of. If seven of us do end up going, we will most likely rent a house in Hawaii via AirBnB (my referral link that will give you $40 off your first rental of $100 or more).

We will probably go with a local hotel (or ryokan) in Kyoto because I would like to stay in a historic district of Gion. Beyond that, we will use renewal certificates from various hotel credit cards to cover one-night stays during layovers. So, I’m not really worried about that piece of a puzzle. It’s the flights that concern me. And for a good reason. On top of having to redeem miles on seven (!) tickets, we will be tied to a cruise schedule, and travel during  peak summer period.

My attitude towards points is that my in-laws are welcome to use whatever I have leftover. We are a very close family, and they help us immensely. Plus, they usually end up covering vacation rentals and other miscellaneous costs, so it all evens out in the end.

In this post I will be focusing exclusively on economy flights. We might pay extra for an exit row seat here and there, as long as the price isn’t outrageous.

Taking inventory of miles and points I have at the moment

Miles and flexible points:

1) 105k Southwest Rapid Rewards points

2) 40k Membership Rewards points

3) 25k Avianca miles in my account, and 22k miles in my husband’s account

4) I have 53k Avios, and my husband has 147k Avios. Due to this new plan, I recently ended up transferring some of my MR points to my husband’s Avios account in order to take advantage of 40% bonus.

5) 130k Jet Blue points

6) 62k Delta miles

7) 5k Citi Thank you points

8) 40k Ultimate Rewards points in my Chase Freedom account that can become transferable if I upgrade to Chase Sapphire Preferred.

My sister-in-law has:

1) 15k Membership Rewards points

2) 25k Southwest Rapid Rewards points

My in-laws have no desire to apply for new credit cards in a near future.

Tackling the puzzle 

Obviously, I can’t predict what award availability will look like in six months, which is the earliest time I can book the awards. But assuming all the pieces magically fall into place, this is what the puzzle will look like:

1) MCO-SFO leg

I’m hoping to fly to San Francisco, but it can be any airport served by American Airlines or Alaska Air with saver flights to Honolulu. We will probably end up using Southwest, and my 105k points should take care of seven award tickets. This leg is directly tied to the next segment.

If you are interested in Southwest Companion Pass, see this post on why now is a good time to pursue it. 

2) SFO-HNL (or LAX-HNL, or…) leg

I’m hoping to utilize Avios points because this route costs 12,500 miles one-way. The key is finding sAAver (lowest level) availability on either Alaska Air or American. It’s not easy, but it is doable. American Airlines releases seven award tickets on its LAX-HNL flights, but sAAver availability isn’t always loaded when the schedule first opens up. Persistence is key.

Cost: 87,500 Avios for seven award tickets. My sister-in-law could transfer 12,000 MR points to her Avios account (she has 500 Avios in it) and book one of the tickets. I would use my 75k Avios for the remaining six seats. The great thing about Avios is that if you cancel, you only lose what you’ve paid in taxes. In the case of LAX-HNL flight, it’s only $6 per person.

See more information on Chase British Airways Visa here

3) HNL-OSA leg

While it’s not the best deal out there, I’m hoping to burn my Jet Blue points on Hawaiian-operated flight from Honolulu to Osaka. The cost is 30k miles+$6 per person. Another alternative is redeeming Avios on JAL, at a cost of 25k Avios+$105.

Since we have seven people, I would need a total of 210k Jet Blue points. I have 130k points, 20k points short from covering five tickets. I can transfer my 5k Citi Thank You points to Jet Blue on 1:1 basis, and 20k Membership Rewards points to get 15k points unless there is a bonus.

The remaining two tickets will be purchased by my in-laws with cash. This route tends to run at $400 per person, not dirt cheap, but not horrible either. I don’t think they will be comfortable taking a chance on a discount carrier Air Asia, but we’ll see.

Heads up! You can still get access to 60k points offer on Citi Thank You Premier card if you use someone’s personal referral link. Email me at milesforfamily@gmail.com if interested. 

4) NRT-LAX leg

After the cruise, we would take a bullet train to Tokyo and fly out the following day from Narita airport. Our best option is to use Avios on American-operated flights from Narita to Los Angeles. Those don’t have fuel surcharges, so the cost is 25k Avios+$40 per person.

We would need a total of 175k Avios. If I end up burning Avios on flights to Hawaii, I would have 125k Avios left. There is a possibility to co-pay with cash at a cost of 1.2 cents per Avios point. However, I have a different idea. I really want to use up my Avianca miles. We would have to redeem them on United-operated flight from Narita to Los Angeles at a cost of 35k Lifemiles+$40.

It’s not as good of a deal as using Avios on American flights, but it would allow me to liquidate Avianca miles once and for all. In order to keep your Lifemiles account active, you now have to actually earn miles every 12 months in order to prevent them from expiring. Not something I want to keep track of each year.

Of course, I would need to top up both accounts first. I can use the rest of  my MR stash (20k points), but would still be 3k miles short. I can add myself as an authorized user to my SIL’s Blue Business Plus card and transfer her 3k MR points to my Avianca account. Boom.

Heads up! The 50k points referral offer on Amex Gold card (more info here) is set to expire on 1/09/2019. 

5) LAX-MCO leg

This one has to be non-stop because Florida is three hours ahead of California. Fortunately, there is a lot of competition on this particular route. I’m hoping to put my Delta stash to good use. The award seats tend to run at 15k miles per person, so my 63k miles should take care of at least four tickets (I hope).

Since I got the card this September, I can even burn the miles at 1 cent apiece toward revenue fare, which is what I will do if award rates are through the roof. My in-laws will have to purchase their three tickets, unless I find a way to get more Delta miles. And I’ll try.

So, if everything goes according to the plan (somewhat unlikely), my in-laws will only need to come up with maybe $1,500 for extra tickets and award taxes. My family of four should be covered completely via miles.

Plans going forward

As soon as I’m done with Terps Visa, I plan to apply for Amex Everyday card using my husband’s referral link. That should net us 25k MR points, factoring in referral bonus. If Delta Card has a 60k miles offer in a near future, I may apply in my husband’s name using my personal referral link. To my knowledge, the best offer right now is 50k miles.

MR points are obviously more versatile, but I’ll still take 60k Delta miles when given the option. At some point next year I plan to give applying for Barclaycard Arrival Plus a shot, but I’m not very hopeful.

Even though I don’t think American AAdvantage miles will come in handy for this particular trip, I still want to apply for Platinum card in January, as soon as I’m eligible for the bonus. You never know how things will play out, and we can always burn AA miles on car rentals or hotels. No such thing as a worthless mile, as far as I’m concerned.

Readers, let me know if you would do things differently with my medley of miles and points. The winner will get a virtual high five from yours truly!

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