Celebrate 10 Cranky Years with an Insane Day of Flying on Southwest

On August 15, 2006, I published “Welcome From the Cranky Flier,” my very first post. Here we are, 10 years and nearly 3,000 posts later and I continue to chug along, writing and putting together painfully awful graphics. Over the next few weeks, I’m going to put up some Wednesday posts focusing on the anniversary. Today, I’m talking about how I’m going to celebrate.

I wasn’t actually going to celebrate this milestone in any way in particular, but then something came along to change that. On August 9, I’m going to fly 8 flights on Southwest between 9 airports, all within California.

Southwest Insanity

Long time readers of the blog know that I’m mileage-agnostic, and I really have no interest in mileage runs. So why the heck am I going to do something stupid like this? It’s simple math.

Southwest put a targeted offer out to some Californians so it could try to boost spending. The idea is simple. Fly 10 one way flights before October 31 and you get a companion pass from then through the end of 2017. For those who aren’t familiar, the Southwest companion pass is a magical thing. Anytime I fly, I can have my companion fly with me for free (well, plus a few bucks in taxes).

I already had a roundtrip from Long Beach to Oakland last weekend (trip report coming), so that leaves only 8 flights to go. I thought about just running back and forth on $39 fares between Oakland and Long Beach a few times, but that wasn’t really going to be all that exciting. Instead, my crack team at Cranky Concierge got to work.

After searching for awhile (on a rare slow day here at Cranky Concierge), David found the golden itinerary on August 9: eight flights and I never touch the same airport twice.

Southwest 1061 Lv Long Beach 7a Arr Oakland 820a
Southwest 2577 Lv Oakland 1045a Arr Ontario 12p
Southwest 2578 Lv Ontario 1230p Arr Sacramento 145p
Southwest 2262 Lv Sacramento 205p Arr Orange County 330p
Southwest 2370 Lv Orange County 430p Arr San Jose 540p
Southwest 3136 Lv San Jose 650p Arr Burbank 750p
Southwest 3188 Lv Burbank 815p Arr San Francisco 935p
Southwest 2550 Lv San Francisco 955p Arr Los Angeles 1115p

This will qualify me for the companion pass for a mere $505.03. It won’t take too many free flights for my wife to pay this thing off handily. This is going to be fun, even though the chance that I make it on to all 8 flights is probably slim.

This plan is fraught with peril. The morning starts out just fine, and I’m pretty sure that airplane from Oakland to Ontario turns into the flight to Sacramento. So we’re good there. But only 20 minutes in Sacramento? Could be tough. The 25 minutes in Burbank and then 20 minutes in San Francisco don’t leave much room for error. So I decided to reach out to Southwest.

I didn’t ask for any kind of fare assistance. No, not at all. What I wanted was to see if they could put a little asterisk next to each flight so that the ops guys could make these priority flights for running on time that day. While I don’t have a guarantee that this will happen, I know that people over there really liked this idea. I’m going to give it a shot, though if the weather is bad thanks to some freak summer rain, I reserve the right to back out if the deck appears stacked against success.

With that caveat, let’s do this. If you’d like to hop onboard a flight or two, that’ll be fun (do it in the morning). My guess is I’ll be doing this alone, so the plan is to just log on and work all day long. And it’ll be a VERY long day. By the time I get back home, I could have already been in Europe or Asia with hours to spare. Yes, it’s completely nuts, but it’ll be fun. In the meantime, let’s play a game.

What's the chance Southwest's operation holds up and I'm able to make all 8 flights?

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They say the 10th anniversary is supposed to traditionally be tin or aluminum. It seems appropriate that I’ll be riding on a lot of aluminum to celebrate 10 Cranky Years. I’m also working on another fun thing. I’m not sure I’ll be able to pull it off, but if I do, it’ll be magnifico.

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