How My 2020 Hawaii Plan has Morphed into a Stopover on the Way to Japan

The other day I was talking to my husband about our 2020  plans for visiting Hawaii. A side note: for years we’ve discussed going to Japan, but never pulled the trigger. The main reason had to do with the  length of the flights. Anyway, I casually mentioned that compared to Japan, flying from west coast to Hawaii is a piece of cake. To which my husband replied: “Well, if I have to get on a plane in LAX,  I might as well go all the way to Japan.”

Stop the presses! I thought I had zero chance of convincing him, especially after making him cram his large body into  tiny economy seat on our recent 14-hour flight from Sydney to San Francisco. And a few other flights. But here was my window of opportunity, so I had to seal the deal before he changed his mind. He said I could go ahead and plan the whole thing. It certainly doesn’t hurt that my husband is a Japanophile. He loves manga, sushi and all the latest electronic gadgets.

I’m more into ancient Japanese culture and primarily want to visit Kyoto. Tokyo scares and intimidates me. Like in any large city, there are obviously freaky things going on. But I think Tokyo takes it to a whole new level, at least based on “Parts Unknown” episode (RIP Anthony Bourdain).

The one I can’t get over is special cafes staffed by women in their early twenties (mostly dressed in school uniforms). They cater to middle-aged businessmen and besides food, their job description is to serve up compliments like “You are so smart! You are so interesting!” By the way, guys, if if you have to pay someone to tell you that you are smart and interesting, chances are, you are neither of those things.

Hmm, I wonder if they have similar cafes that cater to middle-aged American/Belarusian housewives?

But wait, there is more!

I told my sister-in-law about the plan and asked her if she wanted to come along.  I wanted to stick to only Tokyo/Kyoto itinerary, but she decided that we should also do a cruise while we are there. What!? She mentioned it to my husband, who got all excited. Then, my father-in-law heard about the plan and said he ain’t sitting this one out.

Originally, we weren’t planning on inviting my husband’s parents on account of them being old and decrepit. My father-in-law had a heart failure plus a stroke this year alone. He lost his ability to read and we weren’t sure he would be able to handle our trip to South Pacific. The doctors didn’t think he would be around much longer.

But my father-in-law is one stubborn dude. He got on a treadmill, worked hard on learning how to read again, he basically refused to give up. He said that flying for 12 hours in economy to Japan is no problem. Whether this will truly be the case remains to be seen, but for now, the plan is for all seven of us to go to Japan in June of 2020.

That means I should be able to book the flights in seven months, which isn’t that far off. My mileage and points balances aren’t that impressive, but if all goes well, I will cut the costs significantly.

Why stopping in Hawaii on the way to Japan (sort of) makes sense

Our biggest concern is 12-hour outbound  flight from LAX to Osaka. So, my sister-in-law had an idea. Why not stop in Hawaii on the way? I definitely don’t need to be convinced to go to Hawaii, but the main issue is whether my husband can take off enough time in order for us to pull off 5-night cruise, few nights in Tokyo/Kyoto, plus a stopover in Honolulu. This would require a minimum of two weeks.

But I’m very tempted, and my husband said he will talk to his boss when the time comes. Hawaii isn’t exactly on the way to Japan, but it’s a logical stopover point.

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

It takes about 5.5 hours to fly to Hawaii, plus another 8-9 hours to Osaka or Tokyo. So, you are looking at 13.5-14.5 hours in the air compared to 12, not a significant difference. Is Hawaii worth a detour? I’ll let this photo speak for itself.

Of course, for someone who has been to Hawaii already and who is short on vacation time, this may not be the best route. But for some folks, it’s a good chance to kill two birds with one stone. If you fly in economy, sitting 8-9 hours in a tiny seat sure beats 12.

With Southwest entering the Hawaii market, getting to this gorgeous state will soon be easier than ever. Fortunately, getting from Hawaii to Japan is  cheaper than you may think. This is a very competitive route and prices tend to be fairly reasonable. Several low-cost carriers like Scoot and AirAsia have  entered the market, which makes it possible to snag a ticket for as low as $150 one-way. Note that Scoot has just announced that they will soon stop Hawaii flights.

I don’t know how the future will look for Air Asia but right now, they are selling Hawaii-Osaka flights for a very competitive price. See this example in early June of 2019:


Keep in mind that since it’s a discount carrier, you will pay extra for everything. Still, a $189 flight from Hawaii to Japan is tough to beat.

Mileage deals in economy:

1) Virgin Atlantic program

The cost is 20,000 miles one-way on Delta-operated flights from Honolulu to Tokyo. Interestingly, the same award seats run at 30k-35k miles on Delta.com Availability is decent.

2) Lufthansa Miles and More 

The cost is 20,000 miles one-way, and you would be redeeming on United flight from Honolulu to Tokyo. There should not be any fuel surcharges, just a tax of $6. United award availability on this route is pretty good.

3) British Airways Avios 

The cost is 20,000 Avios for flights to Tokyo and 25,000 Avios for JAL-operated flights to Osaka. Be aware that there are fuel surcharges of $100 per person. Availability is pretty good.

4) Jet Blue 

Huh? Hang on, I’ll explain. You can redeem 30,000 Jet Blue points on one-way Hawaiian-operated flight to either Tokyo or Osaka. Those same flights cost 40,000 Hawaiian miles. It’s not exactly dirt cheap, but if you are swimming in Jet Blue points, it’s an option. I may end up going that route, actually. Availability is OK, not great.

5) Avianca Lifemiles 

You can redeem 27,500 Avianca miles (plus $30) on United-operated flight from Honolulu to Tokyo. Don’t forget that through 12/12/2018, you will get a 25% bonus on transfers from Citi Thank You program.

Of course, low-level  availability in  respective partner programs is (usually) required in order to book the award tickets. None of these rates are as good of a deal as paying $189, but if you prefer to fly with an established carrier, those are probably your best bet. Now you just need to find a way to get to Hawaii.

Bottom line

Right now I’m still in the early stages of planning. Will we pull it off? Who knows. But rest assured, this trip will cost a significant amount of money. But that’s the great thing about miles and points. They give you  courage to take the leap, to get off your butt and go for it. Challenging itinerary, you say? I’ve dealt with it before while planning our recent trip to South Pacific.

And I can’t think of  better travel companions than my husband’s family, my partners in crime. Sure, there are times we drive each other crazy on trips, but at the end of the day, those memories we make are truly priceless. I wouldn’t have it any other way. Get on that treadmill, Pops!

P.S. Don’t forget that Tokyo will be hosting summer Olympic games at the end of July of 2020. See Nancy’s related post.

Photo by Sorasak on Unsplash

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Author: Leana

Leana is the founder of Miles For Family. She enjoys beach vacations and visiting her family in Europe. Originally from Belarus, Leana resides in central Florida with her husband and two children.

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27 thoughts on “How My 2020 Hawaii Plan has Morphed into a Stopover on the Way to Japan

  1. Good luck with your trip planning. Just a couple of things to consider. The 2020 Summer Olympics will be in Tokyo. Also, the Hawaii to Japan flights are probably operated by high density planes. If you’re looking at Air Asia, then you are probably fine with that, but you will get similarly tight seating on United and ANA as well.

    • @John Thanks! It’s funny, I totally forgot about Olympics until Nancy has reminded me. We are definitely planning on avoiding that time frame and are looking at June or early July. Not that I’m against going to Olympics, it’s just not the focus of that particular trip. Plus, getting award flights would probably be impossible.
      As far as flights from Hawaii to Japan go, there is a decent chance that we will book JAL. I’ve seen reviews indicating that their planes have more legroom. But either way, economy is economy. I set my expectations low and hope for the best.
      Personally, I would book Air Asia, but with a family I don’t know if I’m comfortable taking a chance. They may cancel the route and then I would be scrambling to find an alternative.

    • @Holly LOL And I didn’t even have to pay you to say that! 🙂 Well, I’m not sure this trip will look the way I envision it. Honestly, we need that Japan cruise like a fish needs an umbrella. I would much prefer to spend more time in Kyoto instead. But that’s what everyone wants.
      I love both Maui and Kauai. Hope you guys have fun!

  2. That HNL-KIX flight gets as cheap as $125. I’ve been watching it for a while. 😉

    You can also pull the same magic on a Hawaii as a stopover to Australia with Jetstar (~$210 one way) , which makes *slightly* more sense geographically.

    • @Ian Yeah, it is crazy that you can fly from HNL to Japan for only $125. I may try to convince my in-laws to give it a go if the route is still there.
      And yes, of course you are right on Australia. My husband’s uncle and his wife flew Jetstar from Hawaii to Sydney awhile back. I was actually the one who found it and helped them book it.

      • Do you just book this flight on the Jetstar website or is there a better way? I’ve been trying to get this exact trip together! Thanks

      • @JB You can use respective websites for Air Asia or Jetstar, sure. Both airlines are bookable via third-party websites, and show up when you do a search on kayak.com So, there is an option to use a travel agency if you feel more comfortable going that route. Hope it works out!

  3. I’m so interested in hearing about your trip planning as I just started my own campaign yesterday in talking my husband into a 2020 trip to Japan! Granted it’s cheating for me because I live in Honolulu so the flight isn’t a big deal but I am pregnant with kid #2 right now so it’s more talking him into the logistics of traveling with a baby versus a long plane ride with a stop-over. Good luck with your planning! I can’t wait to read more.

  4. I’ll be sitting here waiting to see what other destinations or side excursions you will add on. You know it’s bound to happen. Haha. I’m still shooting for just Hawaii this year or next.

    • @Jennifer Oh goodness, I hope we don’t add any more side trips! This will be a sure way to kill my father in law. I wish we could remove the cruise, to be honest. I love cruises, but Japan?! I’m shocked that Doug is willing to go along with this madness.

  5. Leana, you have to keep me in the loop for this trip. My kids would rather go to Japan than Europe…my youngest is even trying to learn Japanese on duolingo. I was thinking of Tokyo and Kyoto as well…I’d love to see Mt. Fuji, Tokyo Disneyland and DisneySea, Owl & Hedgehog Cafes, the Fish Market, etc. They even have a 1 Star Michelin restaurant (inexpensive): https://yelp.to/nm72mAV2CK

    Where would you stay?

    • @Stephanie Sounds good! Since you are based in LA, going to Japan is probably easier than flying to Europe. I say go for it if your whole family is on board. Using Avios on AA flights is a good deal as long as you fly into Narita(no fuel surcharges and costs 25k Avios one way).
      If we add Hawaii, we will probbaly only have two nights in Kyoto, and one or two nights in Tokyo. The cruise would take up a significant chunk of time, unfortunately. But hey, two nights in Kyoto is better than zero nights in Kyoto. I would like to get a hotel in Gion area, to be as central as possible. Ideally, we would get three rooms. There is a cheap place called Laon Gion Kyoto, or something along those lines. Very central and affordable. I’m sure when (or if) I book the flights, I will do a ton of research. For now, this is just a rough plan. It really depends on my father-in-law’s health. A year and a half is a long time. But it’s fun to dream, right?

    • @Russ Thank you! Well, dreaming up the trip is different from actually pulling it off. We’ll see. As my in-laws get older, their health is the biggest unknown factor. Also, our family trips tend to be crazy. But I think I must drawn to chaos or something. 🙂

  6. We are still deciding on whether or not we will go to Tokyo in 2020. But now I’m intrigued by the cash prices between Japan and Hawaii. If award availability sucks during the Olympics, maybe we could pay cash for that portion and use miles to fly back from Hawaii.

    • @Nancy Air Asia must be doing OK on that route since they recently increased frequency from four flights per week to daily. But who knows how things will be in 1.5 years. But yeah, it’s a possibility as long as the math adds up. Plus, stopping in Hawaii isn’t the worst thing in the world!

    • @Army It also stops at Busan (South Korea). I first typed “North Korea”and had to correct myself, haha! All the Japanese ports are places I’ve never heard of, but I’m sure they are worth visiting.

  7. “Tokyo kiree ya nai des. Kyoto kiree des.”

    I took a semester of Japanese at university and I still remember that sentence: “Tokyo is not pretty. Kyoto is pretty.”

    I have never researched Japan but Kyoto must be very pretty! It’s the key example used in Japanese 1001 at the U of M. 🙂

    And I’m starting to think your husband likes to pretend to hate to travel. I think his cover has now been blown.

    • @Talchinski My husband loves exploring places, he just hates flying. The biggest challenge is to convince him to endure the actual journey to the destination. Once he is there, he seems fine. But he loves all things Japanese, so it was an easier sell than I thought it would be.
      As far as Kyoto goes, the photos look really pretty. However, I was surprised by how big the city actually is. I’ve always pictured a sleepy town, but it’s not. Plus, all the famous sights are kind of spread out.

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