I highly doubt that masks for transportation will stop any time soon and I am sure the Canadian border will open up with mask rules still being mandated for air, bus , plane and train. Most likely masks for transportation will be around until Feb 2022 at soonest. I would think the feds need compare the height of the pandemic from last year to this year, which is Nov 1 to Feb 1 before we go putting people on buses , planes and train together with no masks. Plus, other countries are nowhere near where we are. Stopping mask rules on transportation first, then allowing other countries to come in doesn't make sense. I think it needs be the other way around.
Could you imagine the backlash if they lifted that restriction right now and come Jan we hit the same peak or higher as last year? I don't see any upside to the feds changing the rule on transportation any time soon.
Regarding Disney, they could of ended masks, social distancing and open 100% months ago if they wanted, they chose not to. As far as transportation at Disney they have been following CDC for the most, part but I do believe their transportation have to mirror the fed rules for now. If anywhere a business could get out of mask rules for transportation FL is it. If Disney ends mask on their transportation first it would not be a huge surprise, Disney just hasn't been following that path so far.