Hubby and I have always started taking our children to Disney when they were between 18 months and two years. All three children "just know" that we do a yearly Disney trip. (Unless I am really far along in a pregnancy).
Now that they are older, they love to see pics and video of themselves meeting characters for the first time. They don't necessarily "remember" the experience, but they are very familiar with what happened each trip thanks to the fact that DH and I are avid video/picture buffs.
Fortunately all three of mine are pretty go with the flow kind of people, so there was never really any stress involved. We paced ourselves (really, we sort of let the youngest among us set the pace). We both did really enjoy seeing each of our kids experience "THE MAGIC" for the first time...enjoy these days - they are so fleeting and so precious...

Now that they are older, they love to see pics and video of themselves meeting characters for the first time. They don't necessarily "remember" the experience, but they are very familiar with what happened each trip thanks to the fact that DH and I are avid video/picture buffs.
Fortunately all three of mine are pretty go with the flow kind of people, so there was never really any stress involved. We paced ourselves (really, we sort of let the youngest among us set the pace). We both did really enjoy seeing each of our kids experience "THE MAGIC" for the first time...enjoy these days - they are so fleeting and so precious...