I first came up with the idea of taking this trip just sixteen hours ago. I didn’t know for sure that I’d actually be doing so until 10:00 o’clock last night, just 10 hours ago. Now – quite suddenly it seems - here I am strapped into seat 15D on a Horizon Airlines DHC-8-400, winging my way down to Anchorage and beyond in full pursuit of my five millionth mile flown. The fact that I’ll be doing so while cradled in the lap of luxury aboard two of the world’s premier practitioners of the art of International standard First Class service makes this trip all the more exciting.

Let’s back up for a moment and take a look at how it all unfolded…

I live in a cabin amidst towering spruce trees about ten miles outside of Fairbanks, Alaska. It’s been a good winter here in the Interior with lots of sunny days and temperatures often climbing above 0°F, sometimes even into the teens.

Today was just such a day. As I sat at my desk typing out responses to participants’ answers in the Old Timer’s Airline Quiz & Discussion thread over in the Travel Buzz section of this vast site we call FlyerTalk, I decided to take a break from the action and check out a couple of potential mileage runs to be added on to a train trip that I’m taking in April.

When it comes to future travels in any form, my radar is always up. Like a hungry grizzly snuffling around on the tundra in the spring, I’m always sniffing around for good deals. Whereas the bear does it because it’s perpetually hungry, I do it because it’s fun.

Many years back when I was but a wee lad I used to pull out my trusty OAG (that I’d acquired used from the local travel agency) and plan these awesome trips all over the world aboard all manner of exotic airliners. Back in those days “exotic jetliners” meant aircraft like Air Malawi’s VC10 or an Aerolineas Peruvianas Convair 990. Domestic examples included Braniff DC-8s or North Central DC-9-30s. I’d carefully write out detailed itineraries and then sit back, review them and dream. My $5.00 per week allowance never allowed me to venture beyond the realm of fantasy but it sure was fun to visit that realm now and then.

Fast forward to the present and I’m happy to report that yesterday’s fantasies have become today’s reality. For a kid who at age four became fascinated by airplanes following his first flight aboard a classy golden tailed Continental 707, I’ve done pretty well. As of today I’ve logged 5,125 flights covering 4,972,360 miles aboard 178 different airlines.

Now, as I approach the threshold of my 5 millionth mile flown, I’ve been mildly concerned with when and how I’m going to go about crossing it. It is a significant milestone that I’d like to achieve in a style appropriate to the gravity of the accomplishment. I mean, we’re talking Five Million Miles here. Only a tiny fraction of humanity – even here at Flyertalk – has flown anywhere near that many miles. I want to do it in style. Here’s how I’ve crossed my other “Million Mile” thresholds:

1,000,000: September 4, 1985 in First Class aboard a United DC-10 between Seattle and Denver
2,000,000: May 14, 1999 in Economy Class aboard an Alaska 737-400 between Seattle and Anchorage
3,000,000: March 4, 2005 in Business Class aboard a LAN Chile 767-300 between Caracas and Lima
4,000,000: January 27, 2011 in First Class aboard an Alaska 737-800 between Los Angeles and Portland

At present, the only travels I have booked and confirmed for this spring are a six day train trip and the flights necessary to get me to my start point in Chicago, Illinois. Of course I’ll probably take advantage of my time down in the Lower 48 to book a couple of mileage runs but the reality thus far would seem to suggest that if my spring travels stand as planned, I’ll likely be crossing the Five Million Mile threshold aboard a relatively pedestrian 737 of some type.

Well, as I said I’m always sniffing around for good deals and/or interesting itineraries, especially given my ability to turn fantasy into reality these days. I’m sitting on nearly one million miles in my frequent flyer account and as fun as it’s been to accrue all of that mileage, it’s been even more fun to use it. Over the years I reckon I’ve cashed in over 5 million miles worth of awards. And then some.

A couple of months ago I was in daydream mode, tooling around the Alaska Airlines website checking out potential routings for a spring trip. I was looking at airlines like Hainan, Icelandair, KLM, Emirates and LAN just to see what kind of options might be possible. It was a bit early to have a serious look at premium class availability, but the routings and stopovers were there to be examined and considered.

One routing in particular caught my eye. It was on Emirates between Singapore and Houston. Mind you these aren’t published routings like we used to be able to access on Expedia about ten to twelve years ago. No – these days you’re pretty much at the mercy of the airline website and what it chooses to display. To be sure there are ways for knowledgeable people to work the system but it’s a lot easier when the system hands you a doozy of a routing such as I was presented on that day. To wit:

I’d plugged in Singapore to Houston with my primary motivation being to fly the Emirates A380 from Dubai into Houston – one of the ten longest routes in the world and one that would be an attractive addition to my map of international routes flown. I had fully expected to be presented with a nonstop flight from Singapore into Dubai connecting to the A380 on into Houston. The best case scenario I’d hoped for was a flight arriving Dubai early afternoon leaving me enough time to head into town, enjoy a nice dinner and take a hotel for the night. Imagine then my surprise and delight when the following routing displayed for the day I was checking:

DAY 1: Emirates 432 Singapore to Brisbane Depart: 3:15pm Arrive: 12:45am
DAY 2: Emirates 435 Brisbane to Dubai Depart: 8:45pm Arrive: 5:20am
DAY 3: Emirates 225 Dubai to Houston Depart: 9:05am Arrive: 3:20pm

Oh my God! What an awesome routing! I’d get an afternoon departure with an enroute sunset between Singapore and Brisbane and an entire day to bop around Brisbane at my leisure before heading out to the airport for a fourteen hour flight aboard the A380 across to Dubai

Interestingly, this routing wasn’t offered every day nor in every city pair despite the BNE-DXB flight arriving early enough to comfortably connect with a multitude of departures to a variety of US cities. I know because I checked them all. It’s weird because you could have the flights available in First all the way through from Singapore to Houston and yet when I’d plug in SIN-LAX, SFO or SEA – any of which showed First Class available out of Dubai when checking other city pairs such as BKK-SFO, the routing via BNE wouldn’t be offered.

Over the past few weeks I’ve occasionally revisited this city pair, plugging in random dates just to see if it still would come up. For over a month it never did. My assumption was that perhaps it was offered only to provide an extra option during the busy Christmas and New Year travel period. Still, I kept checking. You never know…

So yesterday afternoon, during a break in the action at the Old Timer’s Airline Quiz & Discussion, I headed over to Alaskaair.com to see what’s goin’ on. Like a bored fly fisherman casting his line into the a favorite fishing hole for the umpteenth time, I casually plugged in SIN-IAH for February 18th (four days hence) and settled back to see what I might reel in.

Whoa, Nellie! There it was! And each flight was available in First Class! Holy Cow, Batman! This was the equivalent of an 80lb King on the line! I immediately sat up straighter and began to consider the possibilities. Today was the 14th. If I left tomorrow, I could head on down to San Francisco or LA and catch Cathay’s nonstop across to Hong Kong with connections into Singapore arriving either the afternoon of the 17th or the morning of the 18th. Hmm…

One thing you’ve got to keep in mind is that when it comes to travel aboard Cathay Pacific or Emirates, for me it’s First Class or nothing. Okay, I’d accept Business Class on a shorter flight such as Hong Kong to Singapore or Dubai to Karachi but for long distance sectors over 3000 miles, only the best will do. Besides, I’ve got a great track record on both of these airlines to maintain.

Starting with my first flight aboard Cathay Pacific back in March of 1987, I’ve since logged 25 flights totaling 149,970 miles – all of them in First Class. On Emirates I’ve logged 9 flights totaling 45,180 miles thus far – again, all of them in First Class. That’s a record I’d like to maintain as long as possible.

So then, what’re the chances of scoring a First Class seat to Hong Kong and on to Singapore with Cathay Pacific? It was time to get on the horn to Alaska Airlines’ Partner Desk and find out. Truth be known, First Class on Cathay Pacific can be a tough seat to come by these days. Two things I had in my favor were that I’m only looking for one seat and this is a last minute booking. It’s been my experience on Cathay in particular that First Class award inventory is often released a day or two out. While this is of little consolation to couples who hope to book their travels a month or more out, for an impulsive single guy like me it means there’s a good chance I can make this work. And if it doesn’t, it’s no big deal because we’re in the middle of a fantastic winter here in Alaska’s Interior. Additionally, we’re gaining six and a half minutes additional sunshine every day. There’s light in the sky at 6:00pm now and sunsets have moved from the southern sky way over to the western sky. Even though spring is a month away yet, its promise is tangible. After the long dusky days of December and January, this is a great time to be in Alaska!

So – I get on the line to Alaska’s Partner Desk and initially it doesn’t look good. All of Cathay’s west coast gateways show zero availability for the 15th and 16th. But wait! Without any prompting from me – mainly because I was unaware you could even route this way – my Alaska agent informed me that First Class was available from Vancouver all the way through to Singapore departing out of Vancouver tomorrow night – the fifteenth. Oh no, I thought. The dreaded 1:25am departure.

But no! It was better. Much better! Here’s the routing:

February 15: Vancouver to New York Depart: 9:50pm Arrive: 6:00am
February 16: New York to Hong Kong Depart: 9:00am Arrive: 2:05pm
February 17: Hong Kong to Singapore Depart: 3:15pm Arrive: 705pm

As an added bonus, the flight from Hong Kong down to Singapore would be aboard one of Cathay’s venerable and soon to be retired 747-400s.

When it comes to First Class air travel, the 747 offers – for me at least – the finest First Class cabin I’ve ever flown in. There’s a wonderful and unique ambience to its forward cabin as the windows taper off toward the nose and allow more forward viewing than is possible on any other jetliner. The upstairs cabin ain’t bad either, as evidenced by Lufthansa’s unique seat and bed arrangement which I had the good fortune to experience between Buenos Aires and Frankfurt almost two years ago to the day.

So – things couldn’t have looked better with two exceptions. There was no space available between Fairbanks and Vancouver. Nor were there any seats out of Houston back to Fairbanks. Dang! It’s always the little things that get you! There was space into Vancouver on the 15th, but only on flights that didn’t connect with Cathay’s departure out of Vancouver. Hmm… We’re so close…

I asked my helpful Alaska Partner Desk agent to please confirm the all of the flights between Vancouver and Singapore – costing me 70,000 miles for a one way First Class award – and then I’d see what I could arrange separately between Fairbanks and Vancouver. Additionally, I was able to switch the Dubai - Houston flight over to a Dubai - San Francisco flight. There were plenty of seats available on well timed connecting flights between SFO and Fairbanks.

One of the most valuable benefits of elite status in Alaska’s Mileage Plan is a little perk called “Same Day Confirmed Standby”. Basically, if you’re booked on a flight arriving Vancouver at 1100pm, starting at 10:00pm the night before your travel date you can check in and request an earlier flight. If the coach space is available – regardless of fare category – it’s yours. And so it was that for an extra 12,500 mile one way FAI-YVR award, I got myself booked on a flight departing Fairbanks at 7:40am, arriving Vancouver at 4:38pm, leaving me plenty of time to connect to my 9:50pm departure to New York and beyond. The only drawback is that I’ll have to suffer the indignity of economy class travel between Fairbanks and Vancouver. After 5,125 flights, 60% of which have been behind the curtain, I think I can handle it!

Once I had the Cathay Pacific flights booked, I sped back over to Alaskaair.com and booked the fantastic Emirates routing. All told, this 33,000 mile orgy of First Class air travel would see me gone from Alaska for just six days – a good thing as I’d promised my neighbor Sharon a ride to the airport for her departure to Raleigh on the night of the 21st. I’ll arrive back home on the night of the 20th.

Finally, it should be noted that one of the great benefits of living and traveling alone is the ability to easily and instantly indulge your wildest impulses. Here in the middle of a long Alaskan winter, I just feel like treating myself to some quality First Class service. So there.

Most normal people would never consider a “trip” like this. The more pragmatic amongst us will likely decry this cavalier redemption of hard-earned miles with terms like frivolous and wasteful. Indeed, only the most diehard of airline geeks would ever want to take a trip like this. Having logged 4,972,100 miles aboard 5,124 flights on 178 airlines – that would be me.

Years ago I would never have redeemed this many miles unless I was setting off on a major trip, as in a month or two long. Back in those days though, it felt like I worked a lot harder for my miles. Back in those days I also remember thinking that a half million miles was a huge amount.

Oh well. What can I say? I’m in the enviable position of having an embarrassment of riches in my mileage account. I can afford it. I’m earning the miles faster than I can spend them. So, to any of youse getting all huffy out there over the perceived waste of time and mileage, I’d advise you to stick a sock in it! And don’t forget - the payoff is going to be cracking that Five Million Miles flown barrier in a style appropriate to the feat – in First Class aboard an Emirates A380. Maybe I'll even have a drink with Jennifer Anniston at the bar...

This is gonna be fun!