Award Booking Guessing Game

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My husband turns the big 4-0 next year.  Naturally, we want to plan a big trip to celebrate a big birthday.

So, we will play a quick round of the award booking guessing game.  Here are the clues.

  • 42 minutes actively on the phone with United to get it booked b/c would not work online and gave the booking agent real trouble as well
  • 120K United miles each round trip with taxes about $100 per person
  • Fly on a mix of United, Singapore, and Turkish metal (mostly) in business class
  • Stopover in Amsterdam on the way there
  • Come home via Asia
  • We are super duper excited
  • Pretend price of $42,000 for two tickets

Any guesses?


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  1. Easy. My well known favorite location! 😉 Also the same place I spent *my* 4-0 last year. So sounds like you are doing United to Amsterdam, Turkish Amsterdam to Istanbul to…. fave place … the Singapore Airlines from … fave place …. to Singapore and then on back home through some combo of UA/SQ

    It’s an amazing place, enjoy it!

  2. Just for the sake of variety, I will say IAH-AMS/AMS-IST-SIN/SIN-PVG-LAX-IAH

    IST/SYD will have a stopover somewhere in Asia, so it won’t be the longest flight, won’t even be top 30, and if it goes through the general Europe-Sydney stopovers, United alone will have many flights longer than it.

    SQ doesn’t intentionality release any C/F/R space on their long haul/new config planes to partners.

  3. Gotta be the Maldives! I’ll guess IAH-AMS(stop)-IST-MLE(dest)-SIN-NRT-IAH

    Sounds like my trip this summer on a mix of UA, AC, TK, and OS (LIT-IAH-YYZ(23hr)-IST(stop)-MLE(dest)-IST-VIE(23hr)-YYZ-ORD-LIT). If I had all the hours back I’ve spent on the phone with United on that one through a few schedule changes… Looked at one point at returning thru Asia, but schedule didn’t work. I think my “pretend price” was $12,000 for 2 of us.

    Enjoy it!

  4. Many of you guys have it more or less figured out. It is a place with a Hyatt, and it is Maldives! They did let me route there through Europe and home via Asia, but I couldn’t get that to work online. I had to call in and they didn’t question the routing, but I had already secured part of the award without their help first I will share more details in a dedicated post later this week!

    • ey, should be possible but you couldn’t have the AMS stopover since you would need the stopover in your hometown to add your “free/discounted” Hawaii one-way, assuming that is what you are talking about.

  5. I wish i would have read this two weeks ago. I just booked to the Maldives, but didn’t know you could have a stopover other than SIN or IST. So i opted for the o/w to LGA.

    when you are going?

  6. My hometown is HNL. I was thinking of doing 1st class:

    HNL-LAX-FRA stop UA/LH
    FRA-BKK destination LH

    I wasn’t sure if I could end in SEA or does it have to be HNL.

  7. Our travel plans seem to mirror each other. You’re in Kauai, I’m going there in September. I’m going to the Maldives next March and then you are too. I booked my flights using AA miles and my itin is as follows: PHX-HNL,stopover, then HNL-NRT-HKG-CMB biz and then after buying a roundtrip ticket from CMB to MLE, CMB-HKG-LAX-PHX in 1st.

  8. You are very lucky to be able to take a trip like this without your daughter. If i were to plan a trip like this, it would have to be for 3. 🙁 and that’s many more miles.

    • LMR, indeed. She comes on some adventures, but not on all. For us, this one is better suited for an adults trip. 😉

  9. We are going to Maldives for our honeymoon this Thanksgiving. Courtesy of Hilton devaluation I cleaned out two accounts for Conrad Maldives. Now, I am breaking my head as to how book the trip in business with a stopover in Dubai on the way back. Really not looking forward to going out of the way to Singapore on SQ for the sake of sticking with Star Alliance (prefer non-stop MLE-DBX). If only one could book Emirates one way via Alaska – I’ll even settle for coach!

  10. I can’t wait to read how you are making this happen! I have been trying to put this trip together and have been coming up with some crazy points needed to make it happen!

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