First time on the fly
This is my first time "winging it" on a trip. This trip I am going solo so I do not have to compromise with anyone about mileage, when to stop and what to see. I have a start point and a destination 10 days later. The only hotel I have booked is the one the night before I fly back home.
In the middle, if I am hot, I can walk to the river and dip my feet (or whatever). If I am freezing, I can bundle up and ride until I find a warm place for the night. I'm bringing my tent and sleeping bag but that is just a back up, unless I find a spot I really want to pitch my tent.
I usually plan everything in advance (gas stops, hotel, food places...) so this is a big departure for me.
Am I nervous that I will be SOL when I come to a town and I want to sleep only to find it booked out? Yes. But, I don't have the stress of making it to X town by Z day. Trade off there.
If it sucks, I won't do it again ;-)