I'd say: do the opposite! Don't plan anything, stay no more than two nights at the same place, jump on a train and see where you end up. Then, if you don't like, just take the next train somewhere else.
I did this twice in my early twenties and it was amazing. I mean, it was absolutely horrible. I slept on bark benches, in Cafés, in train stations, before train stations (until they turned on the sprinklers)... I was picked up by the police because we got lost in a field and more than once I was convinced I'd die. But it was absolutely worth it and both trips became core memories / PTSD trigger.
But seriously, don't follow this advice if you have a kid and are not an immortal twenty-something.
Oh yeah, I remember the good ol' "Our whole business Logic is within this 30 tables spread sheet, that only one person can read, and don't you dare restarting that computer" times.
One person. Sitting in front of three monitors. In front of a spreadsheet that maxed out every resource of that computer. It was glorious.