I've been lucky in my life and enjoyed 4 trips coast-coast and annual trips of some sort (either N to NH/Maine or Rockies) since moving to NC. I have 3 more states to tick off (AK, LA and ND), hoping to tick 2 off this summer. When I raced bicycles, I started my training program by riding from SF Bay Area to Mission Viejo during Christmas, along HWY 1. Needless to say, I love being on the road in some form or another. It's my dad's fault, he insisted on a summer vacation every year I can remember, tent, truck camper, small trailer but a vacation or die.
I love this friggen country, am amazed every time I drive across it and love doing so at every excuse I can come up with. I've done everything from sleeping in rest stops in my car to "credit card" camping. Just friggen do it, I've drug my family through my need to travel, just remember its about the journey, not the destination. Some of my most memorable trips, where life-long friendships were made did NOT go as planned.
Make a plan, obsess about it if necessary but leave knowing its a template that can (and should) be modified as the journey takes it. I can get very anal about planning but build in several options in case stuff happens, like finding an amazing spot that nobody wants to leave just because somebody made a plan.
Destination...who cares, just go...I may have said that already. Time of year can make a big difference, there are amazing places close if you want to go somewhere and chill, I love heading west of the Mississippi. Driving from the Mississippi to the Rockies sucks, no matter which way you go, I prefer I40 but that's because I usually shoot for Southern CO, UT, NM and AZ. I'd take the time the week before departure to check with DOT websites for construction/closures to modify the route.
I enjoy going to "group events" like Rubithon, FJCruiser Summit, Katemcy, GSMTR, etc where one goes, unpacks once, off-roads with new friends and goes home, hitting some cools spots along the way. I also enjoy parking my trailer along a random stream in CO and being alone, I've incorporated both in a couple trips. I'm asking myself many of the same questions as well regarding this summer's plans...
Loon Lake on Rubicon Trail CA...
Moab Rim Trail UT...
Black Bear Pass above Telluride CO...
Yellowstone Lake, WY...
Valley of the Gods, UT