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A few weeks ago, we looked at how to split (or not split) group expenses paid with points, and today I thought we’d tackle the overall logistics of group travel with others who both do and do not have points.
The main point for me is that it’s easiest to book award space if I’m travelling alone. The vast majority of my travels are with friends, but we almost always travel separately, usually because we’re going to/from different cities. Often, we’re both on a trip and meeting up somewhere to continue together. If it’s with my partner, I’m booking all the flights with the goal of booking something comfortable and as direct as possible.
I’ve only recently gone on more complex international trips with others who are also “in the points game,” so to speak, and it’s brought both unexpected joys and complications. This is a lighthearted reflection on those experiences.
It’s always worth the effort in the end
If They’re Sorta Points People
For me, these are the most difficult group trips to plan — when the other person wants to use their limited pool of points to book a single destination in a premium cabin on specific dates of a pre-planned trip.
Depending on the level of experience with the other person (usually, it’s a friend whom I’ve convinced to sign up for a credit card or two), I’ll push them to book one year out, when award availability is most predictable.
ANA business class opens reliably one year out
This rarely works because someone who is only semi-into miles & points rarely has enough points to book one year out, is “saving” their points for more urgent trips, and is not accumulating them fast enough to get into the flow of having enough points to book so far out.
Premium cabin award space often appears at the last minute, so many people wait before locking in flights. That approach becomes much riskier when you’ve only collected one point currency, because you’re betting that a single loyalty program will release award space. As the friend travelling with that person, I’m often anxious about whether they’ll even make it to our destination when we’ve already booked hotels, tours, and other activities.
Admittedly, I’ll also rely on last-minute availability, but I’ll have multiple currencies at my disposal and a back-up flight booked.
If They’re Points People
The first thing you might think is that they’re points people, and therefore this is going to be easy. Well, yes and no. While having a plethora of points gives us far more flexibility whenever any award space opens up, we both end up suffering from analysis paralysis or the “optimization curse”.
We’re both trying to accrue elite nights with different hotel programs, and we’ve both flown bucket-list products and want to fly something even better. Every award alert sends us back to the drawing board. Before long, we’re paying cancellation fees for the third time because we’ve convinced ourselves this next routing is just a little better.
Despite our best efforts, we ended up flying Virgin Atlantic’s old business class
If you’re the “points person” of the family, imagine going on a trip with a clone of yourself. Suddenly, there are twice as many Excel budget sheets, twice as many Amex FHR and Chase The Edit credits to optimize, and twice the temptation to position somewhere illogical to book what you believe is a once-in-a-lifetime flight. After all, when will you again have the opportunity to fly first class with someone who appreciates it as much as you do? Someone who sips champagne and understands just how much work went into creating that moment?
If They’re Not Points People
Really, this is the easiest category to handle. There’s an understanding that I’ll be booking flights with points, so we’ll fly separately. The person paying cash will usually book well in advance and then… just leave the booking alone.
I have the flexibility to book whatever flights I want, as long as I arrive there in time for our pre-arranged hotel and activities, and that’s that.
Takeaway
These are, admittedly, all first-world problems. Travelling with friends is a gift in itself, and even better if they also collect points, so we both save money and travel more comfortably. Also, what brings people closer together than 2AM phone calls about cancelling your Virgin Atlantic tickets and flying Condor instead because Virgin Atlantic just swapped your aircraft to its older business class product? Not like I’m speaking from personal experience. 😉
More than anything, these are just observations from years of travelling with different groups of people. Whether your travel companions are deep into the miles & points hobby, just dabble with a couple of credit cards, or couldn’t care less about loyalty programs, each dynamic comes with its own quirks. And each changes how I approach planning, booking, and, occasionally, managing my own expectations.
