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
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
As 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.
Success!
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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Dan Miller travels with his wife and 6 (SIX!) children. He loves to help families travel for free / cheap, especially larger families. If you are looking for help, drop him an email at 
I booked a trip last year when I expected the contract to be signed for a client. Unfortunately I didn’t start for another week. It was too late to change and I was on the hook for the $200 change fee.
I hear you. I do the same a lot – it is called “the commitment fobia”. Even I might have researched the options and determined an optimal one, something stops me from actually booking it. While procrastinating sometimes might get me a cheaper fare/rate at the last moment, 95% of the time it is the opposite: sold out hotels, higher rental rates, inconvenient alternatives… Scrambling becomes the necessity. Why do we do it to ourselves?
I know! Especially with cars and hotels that are generally refundable! Just book it and then change later!
This was a funny read. 🙂
I am exactly the opposite though. I often book refundable things when I have the points and for days I guess will work, and if the price is especially good. I try to fill in the rest later, and if we don’t take the trip, no real loss. Only issue is on the other side where you have to make sure you didn’t miss a night somewhere when finishing the details. The game changes a bit if I pay for flights, knowing that we are locked into dates, but I usually still punt on the hotel if I have time. I currently have some things booked on Expedia (all refundable) for a trip my wife and I may not actually take. I look at it as a foundation for building the rest of the trip.
way to go, Dad! Glad it worked out. I often will do the same thing, even though southwest surely does make things easy for us with the no-penalty cancellation/change policy.
As I was reading your post, I was thinking, hey, wait, didn’t I read somewhere that swa companion bookings could be had as long as “any” seat was still available? Yup, good ole Dariaus…. one of the good impressions/lessons he gives from those detailed “how to” guides of his..
Repost? Comment dates says November 2015.
Clickbait?
Yes, sometimes we repost older articles that are still relevant. As for clickbait, was this article not what you expected when you saw the title?
I don’t think there is an issue with the content not matching the title – the issue is that it’s not readily apparent until the next to last paragraph (“obviously even though this was a few years ago”) or when you get to the older comments.
One place this happens with some regularity is on DoC, but the way they handle it is to put a disclaimer of sorts in the title, saying “this article originally published…” or something along those lines right in the header, or updated info in the first paragraph or two of the body.
Most of those are about card bonuses, so there may be additional content included, and so it’s not quite the same, but it might appease those who get upset about that sort of thing.
Then again, they might just find something else to get miffed about, so you might not spend too much time on it…
Thanks for the (actually constructive) feedback :-).
Not exactly the same but ,recently missed a flight because my watch was wrong . Not feeling very bright !
I booked a motel for a trip a few months away. Looked at this one and that one and found one that was a good deal. Put it through and paid and got the email showing I booked it for the night I booked it. It was 400 miles away and 11PM so not likely I could cancel. Tried to do so but unable to so the great deal was not so great. 🙁