I have never really been able to figure out a good time to do a loaded tour. I have done several cross state tours like Bike Florida, NC Mountains to Coast and Bike Ride Across Tennessee. These are the ones where you camp but the organizers move your stuff for you. This summer I have 4 vacation days dedicated to a bike tour 6 days counting the weekend. Should I just set out from home (Central IA) by myself or do part of one of these rides, but opt to carry my own gear?

I have thought of driving up to MN or WI and touring along the MS river or to various lakes etc. also. I'd leave Friday evening and hotel the first night, then leave the car at the hotel, ride 5 days, return home the 6th.

What would you do in my position? What did you do for your first tour?

I would think about what kind of riding i like (mountains? rivers? plains?) and pick a location to drive to that will get you a loop with that kind of terrain. If your home area is nice, that makes it easier still.

I wouldn't join a supported tour and carry my own gear, that's like, the worst of both worlds - heavy riding, crowded camping - nothing like solo touring.

Also, can you finagle one more day off work - an unpaid day, even? Would that not get you a second weekend, so an extra 3 days riding for the price of one?

I did a little ride from Seattle to Ocean City, NJ via Bar Harbor, ME. But since you don't have that kind of time, do what Valygrl suggests. Her point about adding one more day is a very good one.

Are you familiar witth Adventure Cycling Association?:

Adventure Cycling Route Network | Adventure Cycling Association

You may be able to use some of their routes to plan at least part of a tour. Their Northern Tier route goes through IA and MN, and they have at least one other route that goes through MN and WI.

My first tours were to the swimming hole and back ..