File this under “travel mistakes you want to avoid at all costs”.

I left Louisville to head west for San Diego. My first flight, to Denver, was fine. No complications. I landed in Denver dreading the 2.5 hour layover, so I looked for flights that might leave earlier. Jackpot! There were three total flights headed for SD, mine and two others that seemed to be still on the ground. I headed for the first one and it was almost finished boarding. The gate agent told me it was 100% full, but I hung around just in case. After they closed the door I moved on to the next one at gate 36. There the door was closed but the guy scanning passes told me there were seats, but I’d have to go over to the gate agent for a pass.

I husteled over and asked her if I could get on the flight, and that it would get me home 2+ hours earlier. She was on the phone but took my boarding pass (for San Diego, of course), took a look, tapped something on her terminal and printed me a new boarding pass. Double jackpot! I grabbed the pass, gave it to the scan guy and boarded. Within seconds of my sitting down the plane pushed back. I was very proud of the move I’d made to get home early.

About 90 minutes later I looked out the window and noticed something weird. The sun was on the back of the clouds, and heading west in the evening I would expect it to be on the front of them. Hmmm? Another 10 minutes or so passed and I checked again, thinking maybe we were just on a weird turn before. Nope, sun still squarely behind the clouds. I then used SW’s wifi service to check on the flight route/status, and saw that were were only 110 minutes away from landing…in Orlando!

I turned to the two ladies sitting in my row and asked them where this flight was headed. After they answered “Orlando”, I said something stupid about “that can’t be” and “you’re joking, right?”. They edged away from me a bit, probably thinking I was a nut case.

After a while I pinged for the flight attendant and he was flabbergasted. This just doesn’t happen in the modern system of scanners and computer controls. The rest of the flight was nauseating, knowing that every second I was traveling away from home at 550 miles per hour.

I landed and customer service helped me out, though not much. I got a seat on the first/fastest flight to SAN, leaving six hours from that moment. I found a hotel room where I was able to hole up for about 4.5 hours. And I found that my luggage was on its way to SAN and would stay there.

I still don’t know exactly what happened. I know that gate 36 highlighted San Diego on both the big board and the digital board at the gate. It’s possible that the flight parked there had originated in San Diego, and in my hurry to board I didn’t see the Orlando part. But when I gave the gate agent a San Diego-bound board pass and asked to get on her flight to get home earlier, I would think that would have triggered a question or two. But she was distracted and just printed my new boarding pass with the new destination. And I assumed the destination was the same, so I never looked at the thing. Mistake upon mistake upon mistake.

And so here I sit at 530am, writing this and waiting to board my flight. This is a direct flight (not nonstop, but I don’t have to change planes at the layover point). Hard to screw this one up.

Sometime soon this will be a funny story. Right now it’s just painful. About 18 hours extra travel, 50K miles for my new ticket and a $200 four hour hotel nap. We’re having some fun now…