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Ah yes… the worst feeling in the world – having a vacation mentally planned, but when you go to actually book the trip, you realize there’s a major problem.  This sinking feeling in the stomach has happened to me a couple of times – here’s one example from back in 2015.

Planning a trip to Las Vegas and Phoenix

I took advantage of a sale that Hertz is offering with cheap one way car rentals TO Arizona (though my dates didn’t work out to get a FREE rental)


Of course, as any good denizen of the Extra Miler Club says – “the shortest distance between two points is no fun!”  So instead of the 5 hour drive between Las Vegas and Phoenix, we’ll be going a…. slightly different route


Don’t worry – it’s for counties!

Booking it part-way

I booked my flights (IND-LAS, PHX-IND) a few weeks ago for about $200 one-way and using Southwest points the other way.  I intended to use the $200 flight as my Amex Platinum airline credit, but misread the terms of that, so only got reimbursed for the $11.20 taxes 🙁 (that’s a story for another day)

I also booked the car rental, but not the hotels.  I was planning on taking one of my sons with me as my companion.

Oh no!  Problem!

I had delayed actually booking my son’s companion flight for a good reasons, some of them good, some just laziness.  For instance, I couldn’t change my Southwest Companion Pass companion to my son until I had completed a previous flight, to the Family Travel for Real Life conference last month.

But then I kept forgetting, and putting it off, until yesterday, I went to add him as my companion, only to find…


OH NO!  There were no longer any “Wanna Get Away” fares available for purchase on my flight!  I was under the impression that you could only add a Southwest companion if there were Wanna Get Away fares available.

My heart dropped into my stomach.  I’ve been planning this trip for several months, already told my son about it and got him excited about it, and now it looked like it would no longer be possible.  All of the flights that I looked at seemed sold out.  The dates and locations are somewhat set, since in addition to the Grand Canyon and Hoover Dam, we are going to check one more item off of my travel bucket list by visiting the Veteran’s Memorial in Anthem, AZ that is perfectly aligned at 11:11 a.m. on November 11th

Check out what happens when the sun hits this monument at 11:11 a.m on November 11th

Check out what happens when the sun hits this monument at 11:11 a.m on November 11th

So my location and dates were pretty fixed, and I got bit by the the traveler’s triangle.

This confusion and delay reminded me of when I nearly screwed up our hotel booking in Dublin by not booking in time, to where the hotel sold out (thankfully I was able to eventually find a room there, though we ended up canceling in the end anyways when Aer Lingus canceled our flight)

Thankfully problem solved

thumbs-upAs I walked around, wondering how I had screwed this up and facing the possibility of having to explain to my son how Dad screwed up his trip, I thought of options.  First was to reach out to Kenny from Miles4More, a fellow #FT4RL presenter, who I know flies Southwest a lot.

Before I did that though, I searched around online to see if anyone else had run into my predicament.  I found a post from Million Mile Secrets, which said

You can add your companion to your Southwest flight, as long as Southwest is still selling a seat – ANY seat –  on your flight.  It doesn’t matter if your ticket was the cheapest “Wanna Get Away” fare and the only seats being sold on the flight (when you add your companion) are the most expensive “Business Select” seats.  You can still add your companion

Sure enough, after I called in to change my Southwest Companion Pass companion, the agent was able to immediately book my companion on these flights, even without Wanna Get Away fares available.


Why do I do this to myself?

I don’t know why I keep doing this.  In a world where almost all hotel and car rental reservations are refundable, along with some airline reservations (including Southwest), there really should be no reason for me not to even speculatively book trips.  I know that Kenny from Miles4More does that with Southwest bookings – I’ve seen him post on Twitter that he will sometimes have 3-4 trips booked for the SAME WEEKEND! (And then just later go back and cancel most of them)

I guess it’s a mental thing – for some reason I like to make sure that EVERYTHING is all set before “committing” to anything (even though I know that most reservations are not really commitments at all)

And obviously even though this was a few years ago, I haven’t learned my lesson – see more recent examples like forgetting to book my positioning flights and then forgetting to book them AGAIN!

Have you ever had a trip halfway planned only to find out that the rest of your trip wasn’t bookable?  I want to hear your stories in the comments

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