I began talking to people about what I was planning and the next problem that presented itself was "where would I take the longest walk that I had ever walked?".
A friend and I happened to be driving through Denver and Colfax Ave. presented itself, being commonly referred to as "the longest street in America" by many. I haven't found definite confirmation of that, but I've always been enamored and somewhat fascinated by a road that crosses between States and isn't a highway or freeway.
By the end of the conversation I decided against Colfax, though it may again enter into the plan before this walking is done.
I began by looking for the longest sidewalk. I was hoping for a long, pedestrian friendly, and non-stop walk and a planned pedestrian path in the form of a sidewalk was immensely appealing. My search returned a sidewalk right here in the United States and in an interesting and attractive coincidence a sidewalk along the shore of Tampa, Florida. Bayshore Boulevard boasts the longest continuous sidewalk wrapping up and around the side of a bay with generally nice weather and in a location where I lived.
So, Bayshore Blvd. would be my beginning. Where would I walk to? The sidewalk was not close to the length that I was envisioning for this walk, at 4.5 miles, the longest continuous sidewalk seemed like a great starting point, but it just wouldn't be enough based on my past walks.

I began looking at possible routes from there (and that led Me to begin forming a list of what I would need, including escorts).