My first trip to WDW was December of 1987. I was 29 at the time, also first trip for DH (now ex-DH), and DS4 and DD3 (at that time). I had been wanting to go for years. When I was in grade school, a neighbor and classmate wen to her grandmother's in Cocoa Beach every year. I was fascinated with that and remember watching all the specials about WDW being built.
Finally in 1984 I decided my children were going to get to vacation there and started reading and researching. I bought and read the Birmbaum guide every year beginning in 1984 and joined the Magic Kingdom Club through work. I booked the Grand Plan at the Comtemporary Resort for 4 nights. Construction was taking place on The Grand Floridian and the Swan and Dolphin. Since all our meals were included we did Chef Mickey's, character breakfast at the Polynesian, Melvin the Moose breakfast at Fort Wilderness, Hoop-De-Doo, Mickey's Luau, and the Top of the World Sunday Brunch. We did 2 days at MK, 2 days at Epcot and 1 day at the shopping village. I had read so much about the parks, when we walked in I was able to get us around as if I had been coming for years! I priced the same vacation up a few years later and the prices were astronomical! I think we went at a good time.
We had driven from upstate NY for this trip. We went to Kennedy Space Center and Daytona Beach before Disney and Sea World after. We took about 2 weeks total including travel. Even though the kids were small they were wonderful. When my last son was born, I kept saying he was so wild that we had to put off future trips until he knew how to behave. He had to wait until he was 5 for his first trip.
I had such a great time on that first trip I couldn't wait to return. Fortunately for me, I changed jobs to a new company in 1988 and was "required" to travel to Orlando on business 3 times between 1989 and 1993. In 1989, I stretched a 4 day business trip into a 9 day stay with a co-worker, again the first week of December. My youngest son was only 2 months old at the time but I was able to bury the guilt most of the time by thinking I wouldn't have this chance again. Then in 1990, 3 co-workers and I went to Orlando and managed to squeeze in a day at MK and a day at MGM. On another business trip in 1993, I had two co-workers attend the DVC presentation with me. When I made the decision to purchase in early 1994, they both signed my papers as witnesses since they were there with me!
My next family trip was in 11/94 at OKW as DVC members with my family in a 2 bedroom villa and two studios for my sister and her twin daughters and my younger sister. And the rest is history...