Make sure you have a little poncho for him, it will rain. I don't think 7 nights is too much since the little guy will probably get tired and need some down time. I took mine when he was that age, just me and him. I didn't get him a stroller which worked well for us, when he got tired we would either go rent a Disney one or head back to our room for some down time/swim time. Most important thing is go at his pace. Don't try to do some regimented schedule, if he's tired rest, if he's up early hit it. 7 nights gives you plenty of time to see things so you won't need to rush around. My son was very good about holding my hand or never being too far from me. I was a single mom and took him everywhere with me so he was used to travelling. When we would eat at QS, he would stand in front of me and he had to always either hold my hand or part of my clothes. When I would get the tray, he would hold onto my shirt, I could feel him tugging so I always knew he was there.