This is one of my most favorite subjects.
We first went to WDW as a family in December 1997 at the invitation of wife's parents who owned a non-Disney timeshare. (At Westgate, a terrific place.) Our kids were 9, 6 and 1. Growing up in California, I had been to Disneyland many times, and we had gone there with our kids a couple of times, but WDW was DL x 100! I remember being mouth-wide-open awe-struck by the Swan and Dolphin rising above the trees with the hugh sculptures on the roof. From the moment we drove onto WDW property, I was smitten and there was no turning back. During that first trip it rained hard every day of the week, and we usually returned to the resort soaking wet, but we loved every single minute. We were/are a close-knit family but we had never had so much fun with each other.
At the end of the week, my wife told me that her parents wanted us to come back with them the next year and I actually said that, as much as I would like to return, I didn't want the kids to come to expect an annual trip to WDW. Well, we did return in 1998 and had just as wonderful a time as we had the year before.
Then, in 1999, my in-laws put their timeshare up for sale and had a buyer. I figured it would be a long time before we ever got back to WDW. But then the sale fell through, and I suggested to my wife that we buy the timeshare. We did and the rest is history. We've returned to WDW every December since, and I no longer worry about my kids' expecting an annual trip. In 2002 we bought into DVC, which has only added to the magic.
Looking back, I am certain that first trip was so wonderful in large measure because it was our first visit and everything was new and everything we did we did for the first time. Though no longer "new," our experience each year has the comfortable feel of returning to place where we "belong," where we can set aside for a short time our daily, everyday concerns, and enjoy each other's company and the Christmas atmosphere at WDW.
This year will be very different as our oldest is a freshman in college and will not be with us. But he will be with us next May when we go on our first Disney cruise!