The minute we drive off property! We are all Disney nuts, though my 16yo DD is beginning to get a life. We immediately start the planning process. We decide what we want to try next time, where we might stay(though it seems POR is our "home"), etc. We talk and talk and talk for a few months, planning ADR's, time of trip, finding out when DDs' vacations are and go from there. As far as the actual packing, getting things together routine, I usually start doing this as soon as I book the trip, which is usually at least 6 months in advance. We go in October...I book around March. The trip becomes a reality then and I use every excuse I can to bring out the vacation items. I must get them out of the closet now, lest I forget them later

. I make ADR's as soon as possible and write them all down, lest the crowds dictate we shan't eat at a TS restaurant

. As summer comes to an unofficial end, with the start of school, etc, I start packing the summer clothes and buy more on clearance. I hit the dollar stores and buy goofy things for the room, such as a shoe hanger for our toiletries(saves room in the bath area) and a cheap container of deodorant to prevent blisters on our feet(yes, it truly does work). I also buy a $1 laundry bag to keep our dirty stuff together and I can just carry that to the laundry at the resort. Now, I know this isn't a "What do you take to make things easier" thread, but I just added those tips as a bonus for y'all.
Once it gets to two weeks and less, most things are packed, except for our toiletries and a few other things. This is when I PANIC. What will I forget? What do we need?? What will make our life easier when at WDW? I then scour thru all the threads I have saved and get more tips, which cause me to go out and buy more things. Oh well. I then begin to hope our house won't burn down or that I'll get arrested for some silly reason so as to ruin our lovely trip to WDW.
So, to answer your question...
We start getting ready as soon as we drive off-property
