Most people only consider what time of year they want to go to Disney World when planning their vacation. They plan it around their kids' school schedules, around the peak vs. regular season, etc. Those things are important to consider, but you should also take into consideration the ages of any children that might be going with you.
Under 3 years old: I strongly urge families to take a trip as close to, but before, a child turns three years old since under 3 years old does not require a ticket for park entry. Our first family trip was when my youngest child ~ Andrew ~ was two and a half. He still talks the things he saw and did on that trip. Then again, Andrew constantly is telling me that he "amembers everything" so perhaps my now 5-year-old child is just gifted! :) Sure, there were a few meltdowns over the 6 days and some juggling required since he couldn't do everything, but it was worth it! We had even considered not taking him so we could doing everything with the older two together. But then I realized...duh, we're driving so that doesn't cost any extra. He'll eat free (three and under are allowed to eat off parents' plates, even at buffets). He can sleep in his pack-n-play (fyi- we don't have to count him in the "headcount" of the hotel room...and yes, that matters!). For example: Our first trip, our family of 5 was able to stay in a 4-person room because Andrew didn't "exist." Our second trip, we had to upgrade to a room that would sleep all 5 people...translation = more expensive room. So you see, he was completely free!!! It was a no-brainer. Try to take advantage of this age bracket if it applies to your situation.
Before 10 years old: The reason for our first trip was to celebrate our daughter's 9th birthday. We attempted to surprise her the day before her birthday with a last-minute roadtrip. (That's another story for another post ~ fyi, don't trust my husband Casey with any secret roadtrip.) It has now become a family tradition to go to WDW every 9th birthday of each of our three children. You see, once a child turns 10 years old, they are considered a "Disney adult." This means you have to pay adult prices for park tickets and they can't eat off the kids' menu anymore. Perfect time to plan a trip...before your kids turn double digits. :) Plus it keeps my kids from asking the dreaded question, "When are we going back to Disney World?" They already know. I should tell you that the age span between my 2nd and 3rd child is 4.5 years. This is apparently too long for me to go between Disney trips because we are planning to go again in November 2012 instead of waiting until May 2015 like the tradition calls for. Haha.
