I have nowhere near the experience that the folks above have, but what I found out on my first tour this year was that you need to plan for where you want to be and dress accordingly. I was riding to visit my son, and was expecting to spend several days in Chicago.

What I found was that I could have got by with two sets of cycling clothes (I took three), some pants that zipped off above the knee and two shirts I could wear to museums, restaurants, etc. If you don't plan to go to restaurants, you don't need to dress up for them. I also had a tent, sleeping bag and a couple of penny stoves to heat water for oatmeal and coffee in the morning. Theoretically, I could have heated up some noodles or rice in the evening.

Bring some baby wipes or moist towelettes to wipe the grime off, an extra tube, basic repair tools and you are good to go! Sounds like a fun trip.