I'm not exactly sue how the whole familiar movement thing goes, but we have always played that if you move the familiar can move along with you. But now I am getting zephyr boots and I wanted to know if my floating weapon familiar can fly along with me. Also I have a winged shield, will hat float up with me also?

if your fam is on passive mode it is part of you can goes where u go. But if it is active it only moves when you move it via a move action (so moves instead of you) and it moves based on its move speed and type.

That doens't make any sense. If a familiar can't be more than so many squares from you that would mean you would have to walk only every other round, essentially half speed in order for it to keep up.

It may not make sense but it's the rules. There is a feat that specifically allows your active familiar to move when you take a move action named Active Familiar. There is also another feat that lets you move your familiar with a minor action 1/turn, Quick Familiar. So without those, either you move, or your familiar moves, but not both. On a side note, "keeping up" isn't really a concern because for overland movement you can just put it in passive mode to stay with you, and in combat it's unlikely for the range to be an issue.