The only place that you definitely won't be able to do this is the food court at the Land. No strollers are allowed in that building.
I hear you about the highchairs...you might want to get a highchair cover if you are concerned. We have a very compact high chair cover made by Fisher Price that I bought at Target that doesn't take up a lot of space in our backpack. It's made with a nylon material that is easy to rinse out with a little laundry detergent in your hotel sink at night.