Written by 9:18 pm Travel

Why and How I Got Into the Points and Miles World

If you travel much, and maybe even if you don’t, you are probably aware of the world of points and miles.  And it is definitely it’s own world. (Or maybe even a galaxy.)  

So what is it?  It is the process of earning and then redeeming points or miles earned in various airline, hotel, and credit card loyalty programs for free (mostly) flights and hotel stays.  Frankly, it’s even broader than that to some degree, but this definition is sufficient.  (And to think it all kind of started back in May 1981 with American Airlines AAdvantage.) 

I discovered this world in 2010. This was a simpler time. I can’t recall the first website where I said to myself, “hey, wait a second, this sounds too good to be true!?”, but I soon started following and learning the trade from blogs such as  View From the Wing and then The Points Guy.  

Over the years, both of those sites morphed into something different and I no longer regularly read them.  My go to site became One Mile At A Time which has retained it’s “just a guy with a blog who loves traveling on points and writing about it” ethos. 

So, why bother with the work of earning and tracking points, and then finding flights or hotel stays where you can redeem those points?   Why not just buy the airline ticket, book the hotel night, rent the car and be done with it?  Just like in ye olden days.  

That’s a fair question. And I am completely sympathetic to anyone who doesn’t want the points hassle.  It’s easier to just book what you want and not try and find good deals on travel award redemptions.  Indeed, if I were wealthy enough, I’d probably skip the whole points/miles redemption thing myself. 

Here’s why I (and so many other people) do it.  I can enjoy travel experiences that I could never or would never normally pay for by redeeming points and miles that I earned for transactions I was already going to do –   money I was going to spend anyway.

Case in point: an international long-haul airline trip in business or first class: 

Doesn’t look much like economy, does it? This is an older Cathay Pacific international business class seat. Photo credit: Edwin Leong

Before I got involved in the points and miles world, I had never flown business class. I’m not sure I had even seen a business class suite up in the front of a wide-body jet.  

It’s probably good I never saw an international business class seat because I would have been struck with serious envy.  A business class seat is a massive upgrade from a regular economy seat.  In terms of space, quality of food, service, sleeping comfort, privacy– absolutely everything is better.  Usually far better.  For me, a 6’4″ guy, it’s the difference between an airline flight where I am counting the hours until it’s over, knees often pressed into the seat in front of me, and a flight where I’m sad the hours are passing so quickly and that the experience will soon end.     

But I could almost never justify purchasing an international business class air ticket over an economy class ticket.  The different in price is many thousands of dollars.  For example, Turkish Airlines’ very pleasurable flat-seat business class one way between Washington DC and Istanbul goes for between $6-8K on May 5. That is 10x more expensive than the $730 fare for an economy seat on that date.   Yikes.  (Heck, I can do round trip economy for $1200.)

Enter points and miles.  Instead of me paying up to $8K for that seat, Turkish Airlines will charge me between 65000 miles and 135000 miles plus another $150 or so in fees.  Sweet.  

I actually took this flight last year as the first leg of a Central Asia and Caucasus trip.  The pleasure started with DC’s Turkish business lounge, then early boarding, Turkish’s superb catering and service, great in-flight movies, sleeping on a flat bed, and finally hanging out in their spectacular business class lounge in Istanbul for a few hours at the end of the flight.  

Of course, you’ve first got to earn those thousands of miles using credit cards.  Then you have to transfer the miles to Turkish Airline’s program.  Next you’ve got to actually find available award space on Turkish in order to redeem your accumulated miles, which can be frustratingly difficult.  And so on. 

All this can get eye-wateringly complex.  In addition to the info-blogs listed above, there are many other websites offering paid services to track down those sometimes elusive award seats.  One of the most popular is ExpertFlyer. If you’re going to get that sophisticated (and I usually don’t), though, you had better know your fare class codes.  Like I said, it’s a whole world out there. 

Fifteen years into this, I suppose I know more than most day-to-day travelers – I can pick through  F, J, and Y fare classes, for example, and can quickly identify even second tier airport codes like MSY, NAN, or SCL. But I start getting lost among the R, V, and A fare classes or lesser known airports like EYW (Key West).  In short, I’m nowhere near the level of many folks earning and redeeming miles out there.  But I know enough to have booked some pretty great trips. 

My first award redemption was three round trip economy tickets for the family between Washington DC and Honolulu – 40K United Mileage Plus miles each. Pretty exciting stuff for us but pretty tame compared to what was possible.1

The first big deal business class redemption came two years later.  I knew more now and redeemed mostly US Airways (since subsumed into United Airlines) miles for three business class seats on UA from IAD-EWR-HKG, then traveled on cheap Asia discount airlines through Thailand and Malaysia, then headed home via an open jaw ticket out of SIN-NRT-IAD.2 

Since then, I’ve landed in Sri Lanka, Mauritius, Greece, Uzbekistan, New Zealand, and Chile, among other places, feeling well rested after my relatively luxurious seat experience.  Some of these trips have been with my family, some alone. And those are just the major points redemptions.  

I’ve also used points dozens of times to book shorter domestic trips and many hotel stays – a favorite was five nights (fifth night free when you redeem for four nights!) with Mrs. Anysecondnow at the Ritz Carlton in Santiago, Chile.

Ritz-Carlton pool on the roof.

The points world continues to evolve.  And get even more complicated.  It’s certainly more crowded. Perhaps there are too many enthusiasts chasing too few seats. 

Although I can routinely redeem miles for shorter domestic economy trips, it is unfortunately getting harder to find those holy grail international business long haul seats at reasonable redemption rates. That said, I’m still in the game, earning points on credit cards and looking for opportunities to transfer them to the right airline program for the right seat.

I’m looking to travel next to either Kenya or Tanzania (or Ethiopia?) on the way to my ultimate destination of Madagascar. Nothing available? Well, maybe it’s time to check out more of the Balkans, flying through Paris or Istanbul. I’ll find something, and when I do, getting there really will be half the fun.

  1. Although I soon learned that I’d made an amateur mistake.  I had booked our round trip to both arrive and depart from Honolulu (HNL) in Oahu.  But by the end of our trip we were on the “Big Island”– not Oahu– and had to fly back to HNL to get home.  I should have booked an open jaw ticket (returning from a different airport than the one you arrived at) allowing us to fly back to Washington DC from Keahole (KOA) on the Big Island, instead of wasting half a day flying back to Oahu. ↩︎
  2. We started in Washington DC Dulles Airport (IAD), then flew a short hop to Newark (EWR) where we boarded our long haul flight all the way to Hong Kong. (I did not tell my wife that we were flying business class. I knew I would have one shot at this. She had her neck pillow and was ready to endure 12 hours to Hong Kong in a small economy seat. When I pointed to her spacious seat, she was as amazed and surprised as I had hoped.) On return, we flew from Singapore (SIN) to Tokyo (NRT) back to DC (IAD). ↩︎
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