For our first trip last May, we decided to go and booked everything about three weeks out.
This upcoming trip (mid november) is more of a process. We booked the hotel late last month. Reserved a kennel spot early this month. Gonna book our character meal and tour on the first day of our window. Last step will be the tickets, as DH is military and I don't want to drop that much money before his leave is approved.
That said, I much prefer the way we did it the first time. Having this much time ahead of leaving to figure things out and think it over, etc, has proved a nuisance and our plans have been changed too many times to count due to over thinking/planning. Last time it was a whirlwind of excitement and spontaneity...this time...not so much.