Booking Up

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Perhaps I am just a freak.

Maybe all this early retirement stuff is just a post facto attribution as I try to justify my own neuroses.

Perhaps there are just different breeds of people. Some who enjoy spending, and some who don’t. And I belong to that second strange herd.

In any case I spent several hours today trying to book this summer’s trip to Japan for my family.

Why I did not get this done at the end of last summer, I can’t be sure.

But the time had come to fish or cut bait. And I don’t like dicing worms.


But fishing can be difficult too…

So I spent several hours today putting together an itinerary.

And I’ve got it pretty much set.

Here then are the lessons, fresh in my mind, from my experience booking an international award for my family.

1.  When you are booking an award for five people, you can never have enough different flavors, or total number of miles.

2.  The more miles you have the better. You simply cannot have too many. (Award booking is no place for minimalism.)

3.  Diversification is not just a concept relevant to portfolio planning. It also decreases your risk of failure in booking awards. I had always planned to fly Star alliance to Japan this year because I’ve built up a big nest egg of United and Ultimate Rewards points. But I ended up falling back on my American miles stash, bolstered by topping up my account with Starwood points.

4.  100,000 points is nothing to lift your nose at, even if it comes along with a sizable first year fee on a credit card. (AKA being a cheapskate also has repercussions.)

5.  It is possible to wait on hold for over two hours to talk to an American airlines agent. The excuse: inclement weather in the Northwest. Looking outside my Portland Oregon window I saw only drizzle. Not impressed American Airlines. Not impressed.

6.  Saving $8000 in plane fares is not easy, but it’s definitely worth it. (It should be worth over $16,000 in 10 years.)

7.  Free one ways are a beautiful, beautiful, thing.  (and I still need to tack one on to my itinerary.)

So there you have it, in a Nutshell: the time is right, get churning, get lots of miles, don’t be too much of a cheapskate, and don’t procrastinate.

You are welcome.  And please do as I say.  Not as I do.

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4 Responses to “Booking Up”

  1. Adam March 3, 2014 at 6:13 am #

    Just curious, were you able to find 5 seats on the same flights?

  2. Miles Dividend M.D. March 3, 2014 at 8:25 pm #

    Yes I was Adam. Routed portland to honolulu to kansai.


  3. John August 19, 2014 at 12:31 pm #

    Just saw this article – do you think you would have had as difficult of a time if you booked 11 mos. out? Or do you typically have a headache trying to book your family to Japan?

    I’ll be in a similar spot next year w/ 4 to Japan out of SEA, trying to see if it’s even possible to go direct on miles. Like the blog!

    • Miles Dividend M.D. August 22, 2014 at 5:25 pm #


      Booking a trip 11 months out for a family of four shouldn’t be any problem at all.

      There are lots of Seattle to Tokyo direct flights and one Seattle to Osaka (on Delta).

      It’s always wise to concentrate on the flexible point currencies such as ultimate rewards, membership rewards, and star points.

      Good luck!


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