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There are "wanderers" and there are "planners" and sometimes stles must be adjusted. You sound like more of a planner. Are you willing to search out a place to boondock when you find no available campsites? It's not always a simple thing.
Our trips usually involve other's schedules, so we need to plan it all out. Campgrounds are often packed on weekends and especially so around holidays. Campgrounds near attractions or beaches tend to reserve out early, too, as you said.
Since you are "meandering" plan in plenty of exploring time. Happy trails!
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