Well the most I have biked ina day... about 60 miles, it took about 12-14 hours... as far as luggage why couldnt you have a back pack if it was relativly light, and brining some cash and mainly getting money wired too me (hotels, food etc) I plan on doing it this summer, so time isnt a concern really but im guessing i would take a month or two. as far as hills...i dont think id be walking up any. but maybe im wrong. I have a very tall seatpost, thomson 330 MM. and I dont think i really have anything on my bike thats going to "break" thomson, fsa, FMF, Answer, chris king, srp etc...nothing junk