Full Circle

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It was a little less than a year ago that I began playing the miles game.

It was probably just about a year ago that I spent just under $8000 on plane tickets for my family of five to fly to Japan.

So it felt pretty good yesterday to complete the booking of our trip to Japan this summer using only American air miles and about $400 in booking fees and taxes.

I ended up booking five round-trip tickets in economy from Portland to Oakland to Honolulu to Kansai international and back.

I used 250,000 American airlines Aadvantage miles and 60,000 Starwood miles (which converted to 75,000 Aadvantage miles) all obtained through credit card churns.

I’m certainly no expert in booking award travel, but I learned a lot in the process and I figured it might be worth sharing some pearls (from a novice perspective.)

So here are the lessons I learned from this award booking.

1. Book segment by segment starting with the most difficult segment.

In this award the most difficult segment was between the Bay Area and Honolulu (surprisingly) so I built the trip around the availability of this part of the route.

2. Starpoints are incredibly powerful both for their 1:1.25 transfer ratio to most airlines, as well as to their extreme flexibility in terms of airline partners.

3. When booking with two award accounts, the way you book the tickets makes a big difference in terms of fees. I was originally going to split the families one ways each way between my wife and my accounts which would’ve doubled our telephone booking fees.

By rebooking them as three and 2 separate roundtrips we got around this.

4. Free one ways on American Airlines are close to impossible if you are not originating your travel from an international gateway city.

5. With a family of five you simply cannot have too many miles or miles currencies.

6. Although the best thing about learning the miles game is that it gave me the skills and confidence to pursue early retirement, there’s something pretty darn magical about booking a trip like this for such a reasonable price.

So this was definitely proof of concept.

And although we will not be flying first class anywhere or sampling any of the excellent premium class products this time around I definitely feel as if I won the lottery.

Only in America is such bounty readily available.  Only in America.

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6 Responses to “Full Circle”

  1. Hamster March 9, 2014 at 9:27 pm #

    Nice Alexi. As a physician, and a reader of MMM, I was happy to come across your blog several weeks ago, as I can relate on many levels. We’ve started putting some of this to work and are hoping to get nearly free flights for the family to Korea to visit my in-laws next year.

    I really appreciate the time and effort you’ve put in. It’s a great read and instructive.

    • Miles Dividend M.D. March 9, 2014 at 11:36 pm #


      Thank you for your kind words.

      Flying your family to Korea next year should not be a problem. 2 1/2 2 card churns alone over six months for you and your wife should net you 240,000 Chase ultimate rewards points and United miles each. (2 inks, 1 sapphire preferred, one business and 1 personal 50K mile united cards).

      One benefit of the miles game that I did not appreciate until recently, from the perspective of a high income earner, is the tax-free nature of miles/points. This makes the miles game a very lucrative part-time job. But it’s really too fun to call a job!


  2. Syed March 10, 2014 at 1:48 pm #

    Thank you for sharing your experience and what you learned. I’m planning on booking a family trip to ireland later this year and will keep your points in mind. I have been able to do domestic trips rather easily for a year or so with miles and points but this year will be my first foray into the world of international points traveling.

  3. Miles Dividend M.D. March 10, 2014 at 4:55 pm #

    Thanks Syed,

    You can do it!

    I am not sure what your homebase is, but if you Took advantage of The 100,000 mile British Airways offer earlier this year, I remember there being a very good redemption value on Air Lingus from Boston to Dublin.

    Keep us updated.


  4. Kat J March 10, 2014 at 11:17 pm #

    Congrats on your first year! (almost) Great Job!

    Thanks for your sharing your processes.

  5. Miles Dividend M.D. March 10, 2014 at 11:25 pm #

    Thanks Kat. I saw that one of the card companies is launching quantas cards down under. Time to start churning.”


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