I travelled with a 7 yo, 5 yo, and 7 month old. We chose a monorail resort, which was very helpful. Rolling on and off with the stroller is far superior to folding to get into a bus. We did take midday breaks, though it turned out the baby didn't need them, the mommy did! The baby can sleep anywhere with a comfy stroller. We used both her car seat + universal carrier stroller (this was best for sleeping) and a Citimini double we rented. I had an Ergo carrier, but she was a very heavy baby, and I only found this useful a couple of times. We would typically be up for rope-drop, hit the parks, have an ADR lunch, and then return to the resort for a rest... Enforced quiet time. The big kids had to close eyes for 10 minutes, parents rested, baby played quietly (always napped early in park due to stimulation, often during lunch which made for relaxing meals!), then we would do a swim and have an early dinner and return to park. For AK, we just left around 2:00, and had a resort night. Honestly, the baby was the easiest age to travel with. RS is a wonderful gift for your big kids. We presented it as that... Because of our baby, you get to ride twice! How lucky!