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Over on the Points With a Crew miles and points Facebook group (which you should totally join if you haven’t already) we had an interesting discussion about booking travel for other people.  I thought I’d see if anyone else had any thoughts on it

Reader Matthew posted

Have you guys had a hard time coordinating travel with friends or family who always say how great it would be to travel? But when it comes to planning, you’re presenting all the options based on what they say and just watching the rates increase week after week as they decide? I’m asking because I’ve tried everything over the last few years, and it’s almost never worked. At least a dozen occasions. I can offer a free room, free flight, or just pay me back the taxes, and etc. Some have even confirmed and then canceled, so I just end up cancelling points bookings.

Is it just me? Am I just really unlucky? Or do people outside this hobby appreciate trips less when they’re paid with points? Because to me, it’s totally the opposite! Because DUH.

Image from Flickr

Other people weighing in

It appears Matthew was not alone – here were some other comments from members of the group

  • We have had similar experiences for sure! I think planning travel with a group is tricky in general. Add in people who maybe don’t travel as much or have different travel styles and it gets even more complicated. We’ve had the best luck when planning trips with other friends who understand the points game.
  • I once offered a free room for a staycation to my brother in law + wife that we hadnt seen in a while. They just had to drive an hour to get there and he declined saying there was a squirrel in his attic. You CANT make stuff like that up
  • LOL doing this right now with my parents. I sent them the flight options that they could book with points, on a schedule that worked for them, great deals in business class. And… nothing. “oh yeah, we’ll talk about it later.” I haven’t even gone back to see if those flights are still available yet, because it’s not worth the time until they say “yes, we’re in!” at which point I’ll find them flights and walk them through booking it.
  • I have same issue.. If they dont want to save.. then let them pay the higher cost.. if they let a trip slip through their hands because they waited.. then.. maybe next time they will jump on it.
  • I have had the issue with friends who won’t commit far in advance. Now I don’t bother trying to plan anything with them and save myself the aggravation
  • I have yet to meet my mother in law because of this! We seriously set up flights like every other month and she waits until two or three days before to say yes! And by then the flights has gone up x4! Someday she’ll meet me and her grandkids! Invalid request error occurred.
  • So actually, similar issue.. Knew that Air new zeland would have cyber Monday sale.. Asked my mother if interested in going to cook islands with us.. I just booked her ticket for her.. My sister could not tell me plans that far in advance, so had the option to join us at higher price
  • Yep. I arranged flights and 7 nights in Wailea for 12 people over NYE. Rooms $240 for the week and each ticket less that $50. Still can’t get complete commitment, thankfully it’s all cancellable. I just tell people I’m happy to plan and have them come along but we will be going even if you don’t
  • I have about 2 discussions with people and when I get the feeling they are just talking, I don’t bring it up again. Then I book a trip and they say, hey, I thought we were going together? Say, sure, you can still book it, no problem. They never do. There are doers and there are dreamers
  • Spent hours and hours setting up a multi leg Asia trip using points to find out the guy we were supposed to visit had moved back to the USA by seeing him a bar.

a woman shrugging with her hands up

My experiences trying to book travel for others

I’ve had a few experiences booking trips for other people.  Booking a trip to Europe for my parents went fine – but I was only responsible for flights.  They gave me a window of dates that they were available and once I was able to find saver availability, I gave them the dates.

I’ve bartered miles and points for babysitting a few times, and that’s proven tricky.  For one trip, we were trying to book a 7 day IHG Point Breaks trip, but it proved to be harder than it looked.

(SEE ALSO: Can you book a hotel for someone else?)

For another bartering trip, it took almost 2 years before I was finally able to repay my babysitter with a flight she needed.  On the other hand, booking a trip for my brother wasn’t too bad, even if I did have to suck it up and book a “standard” award…

And of course then was the last time that my sister missed her flight (that I had booked for her with United miles)

How to book travel for others

If you do want to try and navigate the world of booking travel for others, here were a few suggestions that might work for you

  • Easy solution: “Here’s the options, here’s the dates, here’s the cost. You’re deadline is X”. And move on. You’ll go nuts otherwise.
  • Set a deadline even 24 hours and then let it go. In life if it is important people make it happen. I would also tell them that
  • Ask for a retainer

Now it’s your turn – have you ever tried to book travel for others with your points?  What has your experience been?  Leave it in the comments

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