“My Girlfriend and the Airline Agent Look Bewildered at Me Holding My Boxer Shorts.”

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Welcome to the next installment of our interview series where folks share their thoughts about Big Travel with Small Money!

Miles & Points Interview:   Travel Hacking Class

Huntly’s Travel Hacking Class includes 56 lectures to help folks learn how to use miles & points and save money on travel.

Travel Hacking Class - Interview With Huntly

Caitlin and I at the Grand Canyon – The Sunset There Is Breathtaking

How and when did you start collecting miles and points?

My miles and points obsession started 4 years ago.  My boss at my corporate job had been telling me for months that I should sign-up for credit cards to earn airline miles, but I kept brushing him off.

Then one day I was in his office during lunch and he happened to be booking a trip.  I saw him buy 2 round-trip tickets to Asia and pay only $25 in cash, the rest in miles.  That’s when it clicked for me – I applied for 2 high bonus credit cards that same day, and haven’t looked back since!

Why did you start your blog?  What’s special about it?

My blog is special because…it’s not a blog at all!  It’s an online class that covers how to earn and burn airlines miles and points!

I started my class because I know how hard it can be to learn about miles and points when you’re just starting out.  When I first got into the miles game, I was lucky enough to have a mentor (ironically, my boss at my first job).  He showed me how to find and book award flights, how to strategically choose the right miles to earn, and the fine details of how to earn those miles.

That guidance helped me pick up miles and points quickly and take great trips right away.  After mastering everything myself, I realized that type of hands-on instruction was really valuable.  

So I created an in depth online class on miles and points, with lectures and video walk-throughs, to help other people learn the same way!

Travel Hacking Class - Interview With Huntly

Beautiful View of Prague – An Amazing Ancient City

What’s the one single thing people can do to get more miles?

Just like any other miles and points fanatic will tell you, my answer is: opening up high bonus credit cards.  But – it’s important to be strategic with your card selection.

One of the 1st cards I opened up had a bonus of 55,000 miles.  Unfortunately, they were Delta Skymiles.  When I went to go find and book an award trip, I found out the hard way why their nickname is Delta SkyPesos!

What’s your most memorable travel experience?

Last summer I took the most important award trip of my life…a trip to Europe, where I planned to propose to my girlfriend in Paris!  My most memorable experience comes from a SNAFU that happened while trying to secretly bring the engagement ring over there.

After getting the ring, I started getting nervous about how I was going to bring it to Europe in secret.  (The proposal was a complete surprise.)  I definitely didn’t want to put it in checked luggage, but a carry-on was risky too.  What if my bag got searched?

I literally had a nightmare featuring an airline security agent pulling the ring out of my bag and asking me what it was.  Then I’d have to get down on one knee and propose in the airport!  A little less romantic than my planned midnight proposal in Paris.

Travel Hacking Class - Interview With Huntly

Me and Caitlin in Paris…I Proposed That Night!

I decided I had no choice but to bring it in my carry-on.  Everything went smoothly on the flight to our 1st destination, Prague, but things got a little sticky on the flight from there to Paris.  We got to the airport late and were frantically rushed to the front of the line to check in.

The agent hurriedly says, “You’ll have to check all your bags, there won’t be room for your carry-ons now.”

I think, “%*&$!  What the heck am I gonna do!?”  Another airline worker grabs my duffel bag (with the ring inside!) out of my hands, and starts walking away to check it in.  I run over and snatch it back.

“Wait I need to get something out of that!”

My girlfriend screams, “We’re going to miss the flight!  It’s only 2 hours, just get it when we land!”  Now the airline agents and everyone on the line are looking at me.  With my heart racing wildly I say, “It can’t wait, I need this for the flight!”

So I reach into my bag and pull the ring box out, which I had wrapped to conceal.  The only problem is, I had wrapped it with a piece of clothing I knew my girlfriend wouldn’t touch if she had to go into my bag for some reason…a pair of my underwear!

My girlfriend and the airline agent look bewildered at me holding my boxer shorts.  Someone waiting on the line chuckles.  I sheepishly shove the pair of boxers into the shopping bag I’m carrying, and in the most commanding voice I can muster, say, “Alright let’s go, we don’t want to miss the flight!”

Once in Paris the engagement was a success (she said yes!), and it was all worth it.  Even if a bunch of Czech airline agents and an entire line of travelers think I had some very strange reason to need an extra pair of drawers for a 2 hour plane ride!

What do your family and friends think of your miles & points hobby?

It’s always the same – first they’re not very interested, then after seeing the great trips I’m taking, they’re curious and a little suspicious.  And finally, after I show them how it works and help them book their first trip, they’re huge fans!

Travel Hacking Class - Interview With Huntly

Soaking up the Beach in Punta Cana – A Perfect, Warm Getaway for a Few Days!

Is there any tool or trick which you’ve found especially useful in this hobby?

I’d say that thinking about trips 1st and earning points 2nd has been the most useful.  For trip possibilities and miles needed, I use the website Milez.biz, and the interactive flight route maps for my two favorite alliances, Star Alliance and OneWorld.

Then for earning, I head to the Million Miles Secrets Hot Deals page to see the best current offers.

What was the least expected way you’ve earned miles or points?

Around a year ago I booked an award trip for a friend.  When he checked-in for the flight, out of habit, he gave the airline agent his frequent flyer number for United Airlines, which is a partner of the airline program I used to book the flights.  He ended up earning United miles for that trip, even though it was an award flight!

That’s not supposed to happen, but the airline must not have communicated the award flight status properly.  I later found out that this actually isn’t that uncommon, so now I always give my frequent flyer number for a partner program when I check in for an award flight.

What do you now know about collecting miles and points which you wish you knew when you started out?

That not all miles and points are created equal.  There’s nothing more frustrating than working hard to earn a lot of one type of miles (like Avios) only to realize that they’re not right for the trip you want to take (International).

That’s why I cover how to choose the best miles and points currencies in depth in my class on travel hacking.  I also use Million Mile Secrets post categories to research individual programs.

What would your readers be surprised to know about you?

I used to hate flying!  When I was a kid, my parents would always book flights for family trips super early in the morning and with as many connections as needed, to save money.  Their version of travel hacking!

All my childhood memories of flying are of being overtired and of long times spent waiting in airports.  But it’s not that way anymore!

Travel Hacking Class - Interview With Huntly

Visiting the Vineyards in Napa Valley – A Great Trip for Anyone Who Likes Wine

Any parting words?

I encourage everyone I meet to travel more, and to use miles and points to make their dream trips happen.  One of my favorite blog posts ever comes from a nurse who took care of end-of-life patients.  From her conversations with them, she recorded their top 5 biggest regrets in life.

Those regrets serve as wise and heart-moving advice for the rest of us, and reading them always motivates me to do more in life.  That includes traveling and sharing travel experiences with friends and family.

I created my travel hacking class to help people do that, and I encourage you to take the wisdom from that nurse’s post to heart and get busy traveling sooner rather than later!  Thanks for reading!

Huntly – Thanks for sharing your thoughts on having Big Travel with Small Money!

If you’d like to be considered for our interview series, please send me a note!

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4 responses to ““My Girlfriend and the Airline Agent Look Bewildered at Me Holding My Boxer Shorts.”

  1. Hi,

    thanks for the tips. I booked an award flight with United miles to travel on multiple star alliance partners, is there a way for me to get points/miles for a United partner from my United award ticket? If so, which program do you recommend and how to enter my mileage number into the reservation?

    Thanks!
    Sam

  2. I wonder if the courses are designed for beginners or are there things seasoned vets could take advantage of? I’ll have to check out the website.

  3. You keep referring to “hacking”. Do you understand what that word means?

  4. @Sam – You’re not *supposed* to be able to earn miles on an award trip, but sometimes you can if you give a freq flyer number of another program, and that airline makes a slip-up. I’d do it when you actually check in for the flights at the airline counter at the airport. In terms of which program, it depends on your travel needs, but ANA or Lufthansa are both pretty decent programs in the Star Alliance

    @Justin – the course is designed for everyone and is especially useful for beginners. It covers the basics of award travel, but also dives deeper into more advanced stuff like stopovers and open jaws, and the details of app-o-rama’s