Diego Marcia would be a logical stop if they were transporting someone to Gitmo.
They could put the perp on a military plane for the trip to Gitmo.
I like something like that destination (Diego Garcia) or something like that better than to Cuba at large - but there are legal logistics to avoid; presumably however / whenever, they have this stuff all down & pre-arranged ... one of the bylines here is that there’s a new sheriff in town and people are assisting if not just cooperating.