The first time we went to wdw, dd had NEVER been away from my mom for that long. We had always either lived next door to mom or with mom for all of dd's life. She just couldn't imagine going anywhere without her nanny. We went by mom's place of work as we were leaving so that dd could tell her goodbye (we were driving to FL). Of course, dd cried, (and so did nanny!), but about 30 minutes down the road and she was fine. It didn't ruin our trip or anything and she was so excited to tell nanny everything when she came back. So, if grandpa wants to take you to the airport, let him. If dgd cries, she will only cry for a little while before she is distracted and it won't ruin the trip!