Here's how I planned out up coming trip (October). In February, I purchased our airline tickets because the fares were good and low. In April I made our reservations off-site this year, since DH works for that particular hotel chain. In July I made all my PS's for dinner. This morning I purchased 2 7 day hopper passes. So it's August 15th and all that's left to do is pack. An advantage of spreading out your reservations is that you don't have to come up with all the money at once. Hope this helps