For every trip there's at least some level of planning and preparing involved. Even for those last minute "let's go there, we leave tomorrow" type of trips, it's vital that we leave home with at least a base level of our own stuff. It's the determining of what stuff simply must be toted along for the ride and what isn't really necessary.
That last part is a challenge for certain friends of mine that for my safety shall remain nameless. (You know who you are, Mr. Ten-Bags-for-a-Weekend-Getaway.) Defining what is "necessary" can be relationship-testing to say the least. Does your significant other need to take six pairs of shoes for a three day outing? Is that entire bag of electronics really necessary? In most instances making it a road trip solves that problem, there's room to take the shoes and the electronics. However when that road trip is made in a 2-seater convertible, space comes more at a premium. Make it a week on a motorcycle with two saddle bags and two people and it's a harsh lesson in what really are the true necessities. I've made enough of the motorcycle and convertible road trips to have gone from being the traveling fashionista taking along her extensive wardrobe to making sure that I've at least got my toothbrush and enough clean underwear. It's a challenging and somewhat humbling experience to fit a week's worth of essentials into a space scarely larger than a bowling ball.
Before even the first packing begins, which I always wait until the day of the trip to do, there's the planning. I've noticed how some people feel compelled to plan their trips out in painstaking detail. Ask where they'll be at 12:25 pm on Wednesday and they can tell you. They might even tell you what they'll be eating, and how much should be left on their plate at that precise point in time. Of course there's flip side, the anti-planner. That's the one who thinks "drive east" is too specific. They get up one day, call in well to work ("Well, I'm not coming in today") and leave town. If they happen to remember their toothbrush, it's only by sheer luck or that it was conveniently located in their mouth at the time of the decision to leave.
I enjoy a balance somewhere in-between the madness of it all, with a reasonable level of packing essentials and what I deem as not over-planning. Thankfully I married a man who is the same way.
After a few years of being quizzed by acquaintances, I've developed a little of my own form of torment for those planners with the packing question. We have a little conversation that goes something like this:
Them: "Are you all packed and ready to go?"
Me: "Nope. I'll pack the day we leave."
Them: Horrified Silence.
Yes it's a little bit of torture for the uber-planner who has their entire trip itinerary in a spreadsheet, printed and laminated for easy distribution. To those folks, I pose this question: what happens when I find some interesting place in a brochure at a hotel, or hear something from another passing traveler? Some of the most fascinating stops along my travels have been because we saw some random sign about a Natural Bridge in the middle of nowhere Alabama. Or a water tower painted and shaped to look just like a peach in South Carolina, but if you see it at the right angle, it looks like more of an orange full moon, if you get my meaning. It's those random sort of things aren't always "itinerary quality" stops but they definitely make for a more memorable trip. Without that willingness to just let life and the road take the lead sometimes, I'd have a long list of fun memories I'd have missed.
Bottom line, there are times where planning isn't just a good idea but necessity; other times it's great to hop in the car and just go.