Let's look at some ways of making it easier for you when you have to navigate the theme parks in a walking boot. There are no attractions that I am aware of that will prevent you from getting on them with a walking boot.
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Guests have to step down in order to board some attractions like Space Mountain and Rock 'n' Roller Coaster. Cast Members are not allowed to physically lift guests so keep that in mind. If your teenager doesn't have any problems with any of these, then they should be able to ride.
You can ride on anything so long as the safety constraints will work. So something like the California Screamin' Roller Coaster might not work for you. But I would find a Cast Member (employee) near the rides entrance and ask their advice and if they think you could fit into the attraction.
Cast Members throughout the parks are very accommodating to Guests needing a little extra assistance. If you decide that you do need to rent a wheelchair or Electric Conveyance Vehicle (ECV) once you're there, you can also do that at the theme parks.
Yes, steel-toed shoes are allowed at the Disneyland Resort. Just be aware that the metal in the shoes may set off the metal detectors at the security entrances of the resort area.
You might not be able to take your crutches with you on most attractions, but there are places that are close to the loading areas where you will be able to place your crutches so they are close after you finish your experience.
There are no 'conditions' that qualify for a DAS - it is for guests whose disability (which could be permanent or temporary) prevents them from waiting in traditional lines. So, guests need to explain why they can't wait in the regular lines.
If you'll need a stroller or wheelchair throughout your entire visit, there are several local rental companies in Orlando that can provide that service. When it comes to experiencing attractions, a large majority of Walt Disney World rides will accommodate a leg cast from the knee down.
Physical Requirements: Each rider must maintain in an upright seated position with their back against the seatback during the duration of the ride and their arms, hands, legs, and feet inside the ride vehicle at all times. Riders must have one functioning arm and one functioning leg. No leg casts.
Depending on the experience, Guests utilizing a wheelchair or scooter will either wait in the standard queue or receive a return time at the attraction that is comparable to the current standby wait. If you're a Guest who has mobility questions or concerns, please view Services for Guests with Mobility Disabilities.
You will be enjoying your magical vacation in no time. In my experience, most rides can accommodate someone with their arm in a cast, but you will want to check with your doctor prior to your visit to see if there are certain things you should avoid. Water rides, spinning attractions, thrill rides, etc.