My sons first trip was just after he turned 2. My dad & I were the only ones who took him. The beauty of WDW is that there is so much a 2 yr old can do. He loved the Indy Cars (he even drove as he was tall enough-it was a rough ride though), Small World, Dumbo, Carousel, tea cups, Jungle Cruise, train, Pooh, etc. He did not like the Haunted House and still doesnt, and at the time the 3d movies. At MGM he liked the Playhouse Disney, I Shrunk the Kids playground, Little Mermaid, and at Epcot the tame rides. We watch parades and the shows, including Fantasmic which might be too intense for some. At the time, he was afraid of Santa so in prep for the large characters, I got the Sing Along videos (Beach Party, Small World, Campfire) and the free planning dvd. When it came time to meet them, we had to hold his hand for all except Mickey. We saved the character meal for the last day and by then he was used to them.
I dont know how much he remembered on his own, but I think most memories that year came from the videos and pics I took. When we went back a year later, it was a whole other story. From I-4 he recognized DTD and went nuts. He wouldnt stop talking about Disney, CR where we stayed, the monorail, etc (and that stuff was his own memories, not in the pics and on videos). Now we are planning to go in the fall and hes already talking up a storm about all the rides, etc. He still loves the old favs, and fears the big stuff (roller coasters). Hes even telling his 10 mos old sister about it all. I need to start her on the videos so shes ready!
We stay at the CR as I mentioned (monorail-son loves that it runs through our hotel, can see MK and the fireworks, the water parade, and Chef Mickeys is right there which we love). We like the wings vs the atrium too. The first year we went back for lunch and for our son to nap, but we couldve easily have stayed in the parks (I think we needed the break more than him)! January is when we went, and again the following Feb. The weather is iffy temp wise then, and swimming is out. We did have some warm days (70s), but the mornings, and nights were chilly. Stay clear of MLK and Presidents weekends as theyre crowded. Otherwise the lines are almost nil, especially at Epcot (at least in our experience).
alison