As for the urban camping it was the late 80's early 90's so it was a lot simplier then for pulling off that adventure.
Sailing eh? I would love to give that a go. Not in the best place for it on the border of VA and WV. But we have great mountains and moonshine!
The other adventure I want to give a go before I'm too old is a tear drop trailer and hit all 50 states. Low dough, LP tank stove and hit the grocery stores. Planet Fitness membership to get showers and just roll for year. Spend a season in Slab City. Go live on a Res in the Dakotas (I have enough Native to qualify). Hang out w/ the Cajuns for a spell. Just soak in all that this country has to offer :)