I can appreciate the virtues of spontaneity and whimsy, but it seems the converse virtues of organization and planning are not so well respected in popular culture. Perhaps it's just because there's a personality-type correlation between artistic types and a distaste for planning (correlation, not equivalence!) or perhaps it's more endemic.
Consider the idea of vacation travel. Being organized is often equated with "no fun"; one imagines a stuffy bureaucrat with a clipboard and a stopwatch, taking a perfunctory picture of Big Ben, making a tiny tick in a tiny checkbox, then hurrying off to Westminster Abbey from 3:38 to 3:46. The idealized romantic fantasy is that you just grab a few things, hop in the car or on a plane, breeze through some interesting place, and have lots of exciting, unpredictable adventures and experiences.
That's how it happens, too... in romantic comedies. In real life, the person who is being spontaneous may well have a wonderful vacation; I've done the "let's leave tomorrow" trip during peak season and had it all work out wonderfully, so it can happen. But it's far more likely they'll pay twice as much to spend half as much time and do half as many things, they'll wait in long lines and not be able to get in to places they want to go, and they'll come away disappointed.
And there is no reason that a planned trip has to be no fun. The clipboard-and-stopwatch image is an absurd extreme. A more moderate and realistic trip would have blocks of time for things, to make sure to arrive when you need to, and to have reservations where needed, but it wouldn't be broken down to the minute, nor would it be rigidly adhered to regardless of circumstance or whim.
That doesn't mean there isn't a time to get away from some of the organization in your life. Being on vacation (albeit stay-at-home vacation) myself this week, I've just been thinking about that. But you don't have to go to the far extreme; that's throwing out the baby with the bathwater. The trick is to use the right amount of organization, not too little or too much, to suit the activity.
Time is the one thing you can't ever get more of. "Dost thou love life? Then do not squander time, for that is the stuff life is made of." - Benjamin Franklin