If he uses a pacifier, get a Booginhead clip. Booginhead also makes a sippy cup strap that is wonderful. We use both attached to the stroller so there is no loss or dirtying. I use gallon sized ziploc bags for diaper changing stuff. I add four diapers, one outfit, wipes, antibacterial handwipes, and diaper cream to each bag. That way we only need to bring in one bag plus a changing pad into each bathroom trip. I throw two or three of these bags into the bottom of the stroller and replenish each at night before the next day. Add another empty ziploc into the bag in case you get a poop accident and need to bag the clothes. We bring our own high chair cover for trips for sanitary reasons. If you don't have a large floppy sunhat I recommend you get one. We do go back for naps when on vacation but we also try to keep the nap routine close to home routine even in a hotel. We read a story, do milk, brush teeth, change into jammies, etc, just the same as we do at home. I bring a bottle brush and a small travel dish soap to wash sippies and bottles at night in hotels and lay to dry on a towel. If you are flying on a plane to get to Disney, I recommend wrapping little things like presents and having your child open one every 30 mins or so on the flight. It gets then excited to play with whatever it is and makes the time pass faster. I wrapped small boxes of crayons, a calculator, bandaids, stickers, a new book, small stuffed animals, simple puzzles. Etc.
