An open letter to friends of miles & points enthusiasts

I have a bone to pick. I love that so many people in my life come to me for advice on booking travels using miles and points, but in 16 years of being in the hobby, certain assumptions come up far too often. To save the sanity of miles/points enthusiasts in your life, here are the top three misconceptions you should take into consideration the next time you reach out to your resident miles/points enthusiast for advice!

Caviar service aboard Cathay Pacific’s 77W First Class

Just because an experience can be booked on points doesn’t make it free

Capitalizing on an award redemption doesn’t mean you’re in the clear on any other fees or related charges. Many flight awards involve surcharges and can vary greatly even within a single loyalty program. For example, with American AAdvantage miles, you may only be on the hook for a few dollars on a Qatar QSuites redemption, whereas a British Airways Club World redemption through the same program will run you hundreds in surcharges.

Cathay First Class awards can be booked for either minimal or hefty surcharges depending on the program used

With properties, while your room might be free, you may still be on the hook for significant ancillary costs. For example, booking the St. Regis Maldives on points will knock out the otherwise hefty nightly rate, but you’re still on the hook for $745pp roundtrip seaplane flights and you’ll be captive to high food & beverage, spa and activity costs. In addition to budgeting the points required for that redemption, one needs to account for the thousands of dollars they’re likely to spend in relation to that redemption.

It’s not as simple as “tell me which points I need to fly XYZ product”

The miles and points hobby is an extremely nuanced one that, engaged with optimally, requires a deep understanding of complex rules and intricacies of dozens of loyalty programs.

As much as it may seem like it from the outside, many award redemptions are not as simple as “I want it, I got it.”

Learning the nuances of this hobby requires a deep passion for it – and just when you think you have a good grasp on that knowledge base, you find yourself scrambling to stay on top of all sorts of program updates like rule changes and redemption devaluations! A single redemption can involve a LOT more hard work than you may ever see on the surface of a flight someone books on points.

While EVA’s business class is relatively easy to book, other award redemptions require a lot more work than meets the eye

For this reason, next time you want to emulate something the miles/points enthusiast in your life has posted on a sick flight or from a crazy property, and assuming you’ve already properly broached the subject on discussing whether it was an award redemption per my advice in the next section, be prepared for them to respond in one of a variety of ways; for example:

  • If you want to recreate their exact itinerary – for flights, this means the same origin, destination, airline and class of service; for properties, this means the exact same property – it’ll be easy for them to share which loyalty program they used, how many points it cost and which transferrable point currency may have helped them land the redemption.
  • However, since redemptions depend on a variety of factors and any deviation from exactly what they did could change any advice given, they may provide some guidance – for example, letting you know some of the easiest redemptions to the Maldives from the U.S. will likely be on Qatar using American miles or Cathay using Alaska miles – but then ask you to then Google or consult any of their recommended blogs (hi!) for further details.
  • And finally, they may just direct you to Google or their recommended blogs altogether; many sites now break down redemption opportunities by flight product or property. If you know you want to go to the Maldives, there’s definitely an article out there specifically on all point-redeeming opportunities in the Maldives. If you want to fly Emirates first class, it’ll be pretty easy to find an article dedicated exclusively to the various avenues you can take to do just that. I promise your friend isn’t writing you off; there’s just so much information that it’s more efficient for them to not reinvent the wheel and just confirm for you that your inquiries are, in fact, Googleable.
A lot of effort went into booking these Singapore Suites

As much as you may want to “pick the brain” of your resident miles/points enthusiast, you have to be willing to accept that the amount of work that went into a certain redemption may not be easy to explain to a layperson; don’t expect your miles/points enthusiast friend to serve as your own personal travel agent and be willing to put in a bit of work when you’re directed to alternative resources!

It’s rude to assume that the only way a miles/points enthusiast can afford to travel is on award redemptions

Whether or not that’s the case, it’s rude to assume that any or all travel experiences a person is enjoying is thanks to award redemptions. While miles/points can make aspirational experiences far more attainable than they might otherwise be on cash, for many enthusiasts, it’s just one tool in an arsenal of travel expertise.

Regardless of how you think a person may have paid for an experience, your first question should never be “how’d you book that on points?” lest you communicate to that person that you don’t think they could’ve afforded it otherwise. As I’ve had to say more than once to the non-zero number of people who have asked the question: y’all, The Brando will never be bookable on points*.

This view from our villa at The Brando didn’t come cheap, and certainly not on points!

*An exception is if you’re using transferable credit card points as a cash equivalent for booking through the credit card issuer’s travel portals; in this case, your points are actually just being used as a cash equivalent. For example, with a Chase Sapphire Reserve you may technically be able to use >400k Chase Ultimate Rewards points per night at The Brando, but only because those points are technically being redeemed for $0.0125 cash back per point going toward the payment of that room. Chase then pays the property cash for your booking.

Here are a few reasons someone might use miles/points instead of cash:

  • Miles/points can help stretch a budget – by employing award redemptions on one part of a vacation, one can splurge more on another part of their vacation. For example, since we used points for our stay at the St. Regis Maldives, we made the decision to stay in Sri Lanka’s most aspirational (non-points) properties for the second half of that trip. If we had stayed at a property on cash in the Maldives at the rate the St. Regis rooms were going for, we might have considered saving the Sri Lanka trip for another time to space out our spend a little.
  • Miles/points may be a better value proposition in some cases in which a person is perfectly willing to spend cash. For example, I generally try to never use points on any redemption worth less than $0.02/point. For flights, if there is award availability, I’ll do that quick calculation and if it falls below that, I pay the cash rate; above that, I’ll consider using points.
  • Finally, yes – for some people, miles/points may open up experiences that may not otherwise be available to them; for example, a person might never get to a point where they can (or even want to) spend thousands on a flight, but they could take several flights worth that much booked on points over the course of their lifetime. Even in this case, it’s still rather uncouth to point out to someone that the luxuries they are enjoying wouldn’t be available to them otherwise.

When someone saves up and spends their hard-earned cash on a top-tier experience, it can feel minimizing for someone to then assume they only got there with points – don’t be that person who makes such an assumption!

Qatar QSuites are one of my favorite uses of American Airlines miles

So let’s say a friend of yours took an amazing vacation and you think they may have used points for some part of it. How can you politely broach the subject with them?

Easily! Let them know you really loved what you saw of the trip they took and you may want to plan one to the same place or on the same flight product in the future. Ask if they have any tips on booking – let them fill in the rest. Most miles/points enthusiasts are more than willing to let you know which parts they booked on what point currency (see point above).

In Conclusion

It’s safe to assume that your miles and points enthusiast friend has plenty of people coming to them regularly asking for award redemption advice, making wrong assumptions in doing so. Don’t be that friend and be cognizant of these frequent misconceptions; this understanding will go a long way the next time you need that friend’s help!

Raising a glass in Lufthansa’s first class

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