There have been multiple threads on this issue and there are generally two camps: Those, like you, who don't like a rigid schedule, and those like me, who don't want to stress over a place to stay, so we make reservations. A lot of it is based on time as well. You appear to be lucky enough to be able to meander and probably in the off-season as well. I don't have that luxury, so I structure my vacations accordingly. There's no right or wrong way. Do you have definite plans as to where you are going? If so, then maybe a reservation or two along the way won't hurt. If not, then it might be tough to travel together.