I’m part planner, part free spirit.
I love to read up on a place before I go. It doesn’t make sense to go someplace with a rich history, culture and art and not know anything about it before hand. You miss out on the significance of it.
Pre-booking depends on how busy it is. Some places require a reservation or you won’t get in. The Alhambra in Granada, for example. To go to Spain and then miss the Alhambra because you don’t have a reservation would be terrible.
I also like booking accomodations sometimes. When I walked the Camino de Santiago last spring, I booked reservations in big cities, but in the smaller towns I just picked a place I was walking by. That worked out well. In the US on a road trip, I generally don’t make reservations. You never know how far you’ll feel like driving and something is usually available.
There are times when I’ve arrived someplace only to find out the town is sold out for the college football game or because the state fair is taking place, but that’s pretty rare.
But I don’t like to overplan. It’s nice to just do what you feel like doing at the moment and not have every minute scheduled.