[Editors' Note: Earlier posts in this series can be found here (Part I), here (Part II), and here (Part IIb).]

Book ‘Em, Dano

Because JetBlue would only let me book over the phone, I had to go through several annoying steps to get my flights in order. After I had built up my complicated list of interlocking flights and figured out a rough outline of where I would be and when, I had to look on its Web site to make sure the airline actually had flights between all the destinations — in the order I wanted — and had seats available. This led to some frustrating reshuffling as my trips pushed the limits of the airlines network.

Sing them blues, Gene.

JetBlue is primarily based out of New York. It has many flights into and out of the city’s oldest and noticeably aged airport, La Guardia, but a great deal more go in and out of T5, its massive high-tech flagship terminal at JFK International Airport.

JetBlue's T5 terminal at New York's JFK International Airport

Actually, in general, the company has a lot of flights coming to and going from the East Coast. It doesn’t, however, have a whole lot going on over on the West Coast.

You can’t, for instance, get from San Francisco to Portland, or Portland to Seattle, or the other way ’round. To get from one place on the West Coast to another, you pretty much have to fly back to Long Beach — an hour (or three, depending on traffic) outside of Los Angeles — and change planes there.

Given the incredible deal I was capitalizing on, I wasn’t too aggrieved by the situation, but if I were just a regular West Coaster looking to get around the Pacific Coast region, I probably wouldn’t be looking to hard into cramming my plans through JetBlue’s maze of inter-West Coast connections. With All You Can Jet pass in hand, though, my middle names were “Westy Cram.”

I spent several hours figuring it all out and making sure there were seats available. Once I had all the flight numbers and times down, I called in to book them. Again, I had almost no wait time getting to an agent. The agent was super polite and helpful. Each flight (there were around 10 total) had to be input manually — and separately — and then for each one I also had to be confirmed, assigned a seat, and then booked.

The process seemed well suited to making a couple of travel plans — this is probably what it was designed for since JetBlue tries to get most of its customers through its Web portal, but showed its limitations under the extreme circumstances of All You Can Jet travel. It was taking a long time.

After booking the third or fourth flight, my agent noticed that I pretty much always wanted a window seat. She asked me if we could just cut out that step and she’d put me as close as possible to the front door with a window. I agreed and the process moved a little quicker — but still took somewhere close to 45 minutes to finish. Throughout, she remained good-humored.

I asked her at one point, “Is this the craziest itinerary you’ve done so far?”

“Actually,” she said, “it’s pretty typical.”

After that was all done, I called my friends to let them know exactly when I was coming to their respective cities. Within five minutes, I ran into my first problem. For my second stop on the trip, my friend would be at a wedding when I planned to get in. I immediately called JetBlue back — and by strange coincidence ended up with the same agent. She recognized me right away and I had her switch two legs of my trip to accommodate the nuptials. The switch was as easy as pie.

Or so I thought.

In that exchange a terrible, potential CRM-disaster-making secret was lurking.