Well, I'm still trying to work the details, as I've never done any touring before (i've biked, i've camped, but never at the same time).
To add another little monkey-wrench, I want to bring my oldest boy (7) along. He's never ridden without training wheels (will work on that this spring to be sure), so I'm currently thinking about doing a loaded tour with racks/panniers on my bike, plus a trail-a-bike, and (if necessary) a small trailer behind that.
The plan is to take a week to ride from my house (northern twin cities, MN) up to and along the length of the Willard Munger trail to Duluth MN. My wife and other kids would meet us at a hotel (with a pool) at the end and haul us home.
Before doing that, I'll definitely pack the bike and kid, and bike to a nearby campground for a test-run of myself, my son, and the chosen gear.
Am I crazy to even consider this? The route is approximately 170 miles.