Charles Veley is some rich dot-com guy that travels all the time. He is featured on www.mosttraveledpeople.com. I read an interview with him in the Oregonian and was struck by the genus of the answer to this question.
Q: Do you plan ahead or wing it?
A: Plan as if you need to schedule every waking minute, and then, once you get there, set aside the plan. By doing all the planning as if you had control over all aspects of your trip (which you do not) you’ll have enough knowledge to make good decisions when things start going haywire (which they will.)
I’ve never minutely planned everything, or even very much, for a trip because I didn’t want to turn into the anal, planned-every-minute girl. But because I don’t plan every minute, I often have no idea of what I could be doing while on the trip. This seems a great combination. Go Charles Veley. I guess dot-com millionaires are good for something after all.