The only long 'tour' I ever took was a five-day- 440-mile ride from Cleveland to Milwaukee and then on to Madison, visiting family for a week, then ride 480 miles back home. Solo. Yeah, I was only 20 years old. I carried two changes of clothes in a canvas duffle bag, a nylon windbreaker, and a plastic garbage bag over the duffle that doubled as a 'raincoat'... I 'stealth camped' before that was a 'thing' -- sleeping in underpasses and culverts along the way, with maybe (if I could find some) a layer of cardboard between me (in my clothes) and the ground. No sleeping bag, pad, or tent. Yeah, it was August in the Midwest...
To prepare? I couple of years before, I was riding ~500+-miles/week. Recent riding?
maybe 100-200/wk. I blew that away the first day with 97 miles, followed by another 100+- mile day, followed by another, and another... Once I left home, I was committed. Three weeks before school started again in the fall, $100 in my pocket and that was IT. This was back in the day when I could go to Burger King and get three regular hamburgers, small fry, shake
and a pie for under $2.50! Look at the prices from 1978 and call me a liar!
I'd stop at roadside fruit- and vegetable stands or a local 'greasy spoon' diner during the day, and a BK or McDs for dinner... Wash my clothes at a local laundromat every other day. (small towns, gotta love 'em!)
Flat tires? One. But on the way home , I wasn't paying attention and hit a hole which FUBAR'd my rear wheel... I had to trade the LBS (Local? - a 20-mile ride in the back of a pickup truck) my custom wheelset (Phil hubs. stainless d/b spokes, and narrow rims - one bent beyond repair) for a set of generic LBS cheapies to get me home since I had no money left to my name....
Regrets? Absolutely NONE!! Would I do such a spur-of-the-moment, hair-brained stunt again? If I was single without a care in the world like I was back then? Absolutely!!!