Why Last Minute Travel Can Suck & Why People Hate Miles

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Photo courtesy of Jon Rawlinson.

A while back I wrote about how I love last minute travel. How I love to go places on a whim. Well today I am a little stuck because of it and feel frustrated. (I swear that I am making the same face as the guy above.)

This is the feeling that most people get when they try to redeem their hard earned miles. I can’t tell you how many people I have spoken to who have 25,000 or 50,000 miles and have tried to book a simple trip to find out that it is not possible.

Thankfully I am not most people and have backup plans, but I am still a little frustrated. Tomorrow my wife, son & I are flying to Colombia for a week. After that my son and I are staying in South America while my wife flies back for work.

I had a flight picked out from Bogota to Santiago, Chile, but just as I was finalizing all of the other flights around it, the availability disappeared. Oh why couldn’t I commit sooner?

So while I have two other options, it’s the final decision time and the Santiago flight has not come back. We are off to Panama it seems. (And I am mad that the IC Panama is not available on Point Breaks anymore. Boo hoo!)

While I take pride in my ability to travel on a whim, it screwed me this time. I should have committed, but I am so used to waiting until the last minute and it backfired.

Will this force me to change my ways? Probably not. I have been traveling this way for the better part of a decade and I certainly have had more good times than bad.

To put it in perspective, I am complaining about visiting Panama instead of Santiago. Talk about first world problems. While most people find themselves frustrated with miles & loyalty programs, I am continually amazed at how I can travel for pennies on the dollar, even if I have to settle for second fiddle.

Watch for upcoming posts about our actual mileage bookings and our experiences in Colombia and other random places. Wherever we go, my family and I are aware everyday that we are blessed!



  1. I’m just the opposite, Shawn, but becoming more frustrated at my inability to buy and upgrade tix on Virgin Atlantic, my choice for SFO-LHR. I’ve even looked at buying one UC tix and using miles for a second one, which I recently did with AirFrance/Delta. Virgin can’t seem to make up its mind when to release the first class space … up until a couple of years ago, I could sew up a great trip 11 months out for two of us, now there’s very little availability. New York is much easier, 3 airports, lots of flights but I prefer the one daily n/s from SFO. So I am practicing that face above!


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