Really, there's only one answer: just have fun.
If taking a detailed, fully planned trip is what does it for you, then by all means run with that. Want to wing it on the fly? No problem. Trailer the bikes to get to the good stuff? That's great. So long as you're enjoying yourself and the trip then that's the right thing to do.
Being a little more pragmatic, I tend to plan things a bit more when I'm shorter on time. I'll do my versions of Shamrock Tours (ala Roadrunner Magazine). Find a center hub then take day rides originating out from the hub in four different general directions. They tend to fit well into your average person's week off and can be as minimally or maximally planned as you want. Hell, there's plenty of times where I've felt like just trailering the bike to do a hub-based tour -- especially if lugging along camping gear -- but lacking a hitch, trailer, and a place to store said trailer I just deal with the inevitable point A to point B rush. Besides, outside of climate control my sport bike and car are the same in long distance comfort, so it mostly comes down to squaring off my tires and gas money.
In three weeks I'm taking off three weeks from work without any solid plans. Just me and the voices I bring along in my head (and probably ADV from the peanut gallery since I'm most likely going to be doing a live ride report). I might figure out an interesting route for the day and take that, point my tire and go in some random direction, or plop for several days and basecamp.
Anyway. Moral of the story is to give it a try. Can't hurt to try a trip without planning or seeing how a trip goes with trailering. It's your ride, so enjoy it, however that enjoyment may come.