Graeme (out CTO) and I went through a marathon 6-hour session on how the heck we’re going to make this trip happen — let alone the logistics of video blogging and a myriad of other details. Keep reading to see what happened. I had some things I have been dying to blog about and wanted to make sure we went through all the pain that everyone does from booking to traveling so we could discuss how to make things less complicated…

First, I wanted to purchase all the tickets using each airline’s website — this way I could review on my blog how easy it was to both purchase and change tickets — as we knew we would probably have to change tickets from time to time as we got deeper into the itinerary. And don’t forget, time was running out on us because we were well inside the 14-day advance-purchase window (for leisure travel), plus,we’d documented 10-attempted airfare increases since Labor Day weekend. So, we knew this wasn’t going to be easy — or cheap.

Not to mention, I had to re-learn grade school geography! We put up a crude map on a big white board in my office,with all the states and the major cities in each state (an aside: Graeme, who is from Scotland, knew more about geography than I did — or at least I let him think so …)

Anyway, we both knew the key was going to be getting to/through the states that had airports with very few flight options — and, we wanted to make sure all the connections were at least one-hour long (even though we knew such “perfect world” connections wouldn’t always be possible).

And, remember, this had to be super cheap, because — we are cheapskates! We don’t have a big marketing budget; in fact, we don’t have a marketing department at all!

So, we pulled up our database of world-wide flight schedules and began writing custom queries to analyze our options; we also pulled in the cheapest airfares from our database (the database that powers our website) to check all the possible route combinations between cities (and there are millions, as it turns out). We wanted to map out how to make our purchases, while optimizing any back-tracking routes.

We decided to tackle the tough areas first: the swing through Rhode Island, Delaware, New Hampshire and Maine, and also the area of Western states that includes Montana, Wyoming, and North and South Dakota.

Meanwhile, time is running out: we need to start purchasing tomorrow to stay outside the 7-day window,as we want to start this trip this coming weekend.

But at least now, we have the basic plan; it just needs some fleshing out…