It's a fun idea, and props to the person who did it.
But, but, but: obviously you can still drive from A to B, but don't forget that On the Road documents trips taken before the Interstate system was built, so the whole thing takes place on roads that are now mostly sleepy backroads or completely vanished. I guess a similar caveat applies to the various urban locations described. I haven't looked at the ebook, but I hope the creator made an effort to use those backroad routes instead of the Interstate wherever possible.
Also, On the Road is such an odd book... it's not especially difficult, but it seems to get more difficult as I get older (and I know I'm not alone in having that response to it). What was once exciting, revelatory and profound for 17-year-old me -- wow, such rebels and free-thinkers, and 20 years before the Summer of Love! -- just seems kind of shallow and self-indulgent to 47-year-old me.