Editorial
AwardTraveler of the week
Editorial

Godfather of the Skies: Meet The Guru of Points & Miles who Flies Around the World for Free

Every day we track down a great award traveler. For this week, we are honored to present you - Gary Leff from View From The Wing! Throughout his over-40-year travel life, Gary has been influencing the whole award travel industry for decades with his professional insight and word of wisdom. Read below for some of Gary's tips for newbies and also some of his "Best Points Deals" he's ever redeemed.


Hi Gary, can you tell us a little about yourself, like the city you grew up in and go-to song when in a good mood?
I was born outside Ft. Lauderdale, grew up in New York, went to school in California and then moved to DC after college. 18 years later I moved to Austin.  So “I’ve been everywhere, man.” At least in the U.S., large enough to matter, and that isn’t absurdly cold. Here are, I think, the very best songs about travel – led, of course, by Iggy Pop’s The Passenger.

You’ve been writing View From The Wing since 2002, that’s a really long period! What made you begin the point-collecting life and how do you stay persistent?
I started paying attention to miles and points after graduating college. My family let me use some of their British Airways points for American Airlines travel to fly from home for visits. I was flying a lot myself, for work mostly, and I signed up for everyone’s programs along the way. I got a US Airways credit card in 1997. And I used to read all the fine print in the newsletters airlines would send.

I started to blog about miles and points to document what I was learning along the way, because I was constantly getting questions, and because friends were starting political blogs at the time and I didn’t have anything truly unique to offer in that space.

It’s not easy to maintain a rigorous blogging habit with such a busy career like yours. How did you find the balance point between the frequent flyer career and your day job?
I do the things I love, there’s not a huge difference between work and non-work (other than, I suppose, whether someone is paying me). Writing about miles, points and travel is what I want to be doing and thinking about, so it isn’t really work.  And since I get up super early and start working – day job, blogging, what have you – I just keep doing both as-needed throughout the day and into the evening.  On planes thanks to inflight internet I keep working non-stop as well.

Singapore Airlines Suites - AwardTraveler of the Week: Gary Leff

As the so-called “Airline Industry Brainiac,” what is the best advice you have for becoming an award traveler? What’s the first step for points rookies?
The first step with miles and points is just to sign up and pay a little attention, it’s possible to overwhelm someone with advice. There’s so much knowledge and complexity it can seem overwhelming and not worth it.  Airlines used to offer miles when a customer would deplete their account of points, they were worried the customer would no longer have a reason to be loyal once they’d earned 25,000 miles in their account.  They learned the opposite was the case – once you’ve redeemed for an award your accumulation speeds up. You’ve proven to yourself you were making a good decision, that you’re getting value, so you’re willing to keep investing time and attention.

Throughout your over-30-year award travel life, what’s the best points deal you’ve gotten in your award travel career?
I’ve been traveling since I was a little kid. My parents were divorced and I used to fly back and forth – first with my dad flying to pick me up, and then when I got older as an unaccompanied minor. I had family move to Sydney when I was 5. So my travel life dates back around 40 years. And my award travel life dates to the 1980s, though I have to admit allowing American Airlines miles expire around 1993.

I used to upgrade on United and earn more miles from class of service bonuses (based on the cabin flown rather than ticketed) that I made miles off the upgrade.  Here are what I think are the best miles and points deals ever, and my favorite recent award booking values.

According to your interview with Map Happy in 2015, you said you like Singapore Airlines and Cathay Pacific the most, could you tell us why?
I love Singapore’s food and service, and their Airbus A380 Suites Class is great. The 10 year old Suites product still holds up, but I still haven’t tried the new Suites they unveiled in the fall. Cathay Pacific offers one of the most consistent products, and their first class bed is among the very best for sleeping.

Singapore Suites Center Seats Become a Double Bed - AwardTraveler of the Week: Gary Leff

From 2008, you have written over 110 flight reviews on View From The Wing, and you’ve had the chance to enjoy many gourmet dishes in the air. Which airline offers the most finger-lickin' good food in your opinion?
Gosh, it’s probably a lot more reviews than that but I’ve failed to catalog them. The best main dishes are on Singapore Airlines, their book the cook especially departing Singapore is amazing. I’ve rarely ever had laksa as good!  ANA and Asiana have exceptional meal service. I’ve found Etihad to be the most customizable – a flight attendant trained as a chef can mix and match ingredients, and you just look at the menu to figure out “what’s in the kitchen” and you can suggest a dish.

Singapore Airlines Laksa - AwardTraveler of the Week: Gary Leff

From your interview with Wendy Perrin, we knew that you are always open for trying out exotic street food, but what’s the most bizarre food you’ve ever eaten in your life?
If I’ve eaten it and enjoyed it, it doesn’t seem that exotic to me, so I guess the only way to answer this question is with where I draw the line. I don’t eat beetles or scorpions on the street in China…

Beijing Street Food - AwardTraveler of the Week: Gary Leff

Are you using any useful hacks/tools to assist you in planning trips or finding award tickets?
For everyday searches I use the KVS Tool. I’m lazy and so I like to set up a big search with AwardNexus which lets me search multiple routes and airline alliances at a time across a range of dates. I use ExpertFlyer for email alerts about when space I’m looking for opens up. All three are paid services but I use them enough they’re a value tome.

This one is more like gossip: What do you think of One Mile At A Time?
Ben Schlappig writes the best travel blog on the internet, it’s the one I read most often.

Though View From The Wing has become one of the most successful award travel blogs of all time, are there any do-overs you would like another chance at, if you could start your blog all over again?  I’m the luckiest guy in the world.  Why would I do anything differently?  I just write what I’m thinking, as though nobody’s reading, and I’m fortunate enough that people read it anyway.   

What’s next?  What’s next for me is really a function of what’s next for the travel and loyalty industries. I speak at conferences regularly and get an insight into where airlines, credit card issuers and payment networks, and loyalty marketers are going. I don’t always like what I see, but I try to figure out how to navigate through it all to have the very best travels that I can and share my thoughts along the way.

Editor's Bottom Line:

We really appreciate Gary’s time in sharing his life stories and thoughts. For the AwardTravel Editorial team, it’s been a pleasure to work with Gary. He has embedded words of travel wisdom for our readers. No matter whether it comes to points & miles or travel experiences, Gary never hesitates to share his thoughts with readers, and we believe that’s the major reason View From The Wing is beloved by all and has been for many years.

Interested in Gary's favorite airline cabins? Check out our Singapore/Cathay flight reviews: 


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