I agree with talking to your MD and considering a wheelchair or ECV.
I had to travel for work while wearing a walking boot. Just the travel part -- airport, flying, connection, flying, airport -- was enough to make my foot/ankle and therefore knee and therefore hip most unhapppy. I was fortunate that I was attending a training class so could sit most of the time at the destination. I cannot imagine even attempting Disney in a walking boot unless using a wheelchair or ECV.
Also, if you will be flying: my boot had air bladders in it that inflate to hold the limb in place. As the plane ascends, the air in the bladders expands. I had not thought of this on the first leg of my journey (oops). We were ascending after takeoff and suddenly my booted leg became rapidly extremely painful as the air bladder quickly inflated - we're talking it went from fine to very very painful in seconds. It took a moment for me to remember physics and realize what was happening. I then had to unbelt myself and scramble reach the boot and to deflate the air, all in the cramped confines of economy class. I deflated it all the way and left it that way until we were at altitude then carefully inflated it again, though not fully, just in case. As we descended the air "shrunk", and I had to reinflate it again once we were on the ground. For the rest of the legs of the trip, having learned the painful lesson, I deflated fully once I was boarded and seated, inflated some once at altitude [enough to keep the boot in place, but not fully inflated], then reinflated once back on the ground: problem solved.
Also, going through airport security is a bit of an adventure with a walking boot. Since I was not permitted by my MD to walk without it, I was allowed to go through the magnetometer with it, get wanded and patted down, then sit, take it off, and they passed the boot through the xray machine and then swabbed it, while I took off the sock and they checked the leg that had been in the book. I feel sorry for the person doing the pat-down, but did warn them in advance the sock and leg/foot would be stinky from being in the boot. So, allow lots of time for security screening. They directed me to the lane for those with special needs, which probably also helped. There was no rush, and they had dealt with walking boots before so had a process (actually, they had a couple options, which they explained to me and let me choose from) and knew what to ask and how to assist.
SW