On Magical Express between MCO and resort, checked luggage may not travel on the same vehicle as passengers. Checked luggage with yellow ME tags gets transported between MCO and a Disney resort via trucks, handed off to bell services, and then delivered to your room. You may have carry-on bags that you hand over to the ME driver at MCO and it goes under the bus for the trip. You retrieve it from the bus driver at the resort.
On the
DCL bus between a Disney resort and the port, your checked luggage with the colored DCL tags gets picked up at your resort room on your embarkation day and is transported between the resort and the port via truck. You may have carry-on bags that you hand over to the bus driver at the resort and it goes under the bus for the trip to the port. You retrieve it from the bus driver at the port.
On the DCL bus between MCO and the port, your checked luggage is handled similarly to the resort to port trip, so it may travel in a different vehicle (i.e., a luggage van rather than the bus). Your carry-on bags will go under the bus you ride, and you retrieve them from the driver at the port.
On the DCL bus from the port to a Disney resort, your checked luggage will travel under the same bus as you take to the resort, along with your carry-on luggage. Same thing going port to MCO, unless you are flying on a participating airline where you can check your bag from ship through to your home airport. Never used this myself, since Southwest doesn’t participate in that program.
We usually have a rollerboard carry-on bag and a messenger-style camera bag (like a soft-sided laptop bag). We hand over the rollerboard bag so it travels under the bus, but I carry the camera bag onto the bus and place it on the floor between my feet once on board the bus. I don’t like to have that bag out of my direct control, since it has medicines, cameras, and some small electronics that I would not want lost or damaged.