Gitmo taxi service is busy today.GTMO842 & GTMO844en route to the 'holiday' camp.
Catching a pair of these heading in the same direction close together is not too common.
Generally they operate a shuttle with one outbound & one inbound.
Not so common for two to be heading in the same direction fairly close together.
That said I have caught three GTMO callsigns airborne at the same time before now.
That is my thought too.
Gitmo bus service you wait for a while for one and then two show up together.
Winchester is radio brevity code meaning 'out of ordnance / no ordnance remaining'