I did my first 'tour' - meaning a longer than a weekend excursion - back when I was in my early 20s and just laid off from my job. I was also used to riding 40-50 miles/day, and had gone on a number of organized century (100-mile) rides. I had nothing to lose, so I set off to visit family in Wisconsin - and I'm in the Cleveland OH area. 1000 mile round trip.
I set off with a spare change of clothes, some plastic garbage bags, a canvas duffle bag, $100 and my tool kit. No tent. No sleeping bag. I did what is known as 'stealth camping' by sleeping under bridges, in culverts and under trees alongside the road. I made it to Madison in just six days, averaging 85 miles/day. It was riding into the prevailing wind that knocked the heck out of me, not the saddle time. I ate at local diners, mom&pop greasy spoons and even McDonalds when you could get a good meal for $2. I even stripped down to my skivvies and did laundry at a laundromat somewhere in Indiana...
Back then my bike was just a regular old 'ten-speed' - My '75 Fuji that I still have today, although it has been upgraded several times through the years...
That trip is something I'll always remember. The kindness of strangers when I'd ask to fill my water bottle. The incredulous look on the face of the woman at a roadside vegetable stand where I stopped to buy something to munch on when I told her that I had already ridden 75 miles that day... Now that I'm semi-retired, I'm planning another three-week 1000-mile tour.