Two bits of info, can't say how helpful, sort of contradictatary.
>pic related (no source)
>at GTMO is a Navy/Marine base, this time of year they have what is called “sleigh rides”, sleigh rides are flights for those living on the base, both contractors and military personnel to get off the island for the holidays. Now because EVERYONE can’t go on leave at the same time there are two sets of sleigh rides, and because not everyone wants to go home to the same parts of the country, typically there are sleigh rides that land in the U.S. and take off to return residents to the island after leave from 3-4 different points within the U.S. What this looks like is, the first leave period goes from say 12/17 to 12/27 and the second from 12/27 to 1/7 or something similar. So on those days you will see multiple flights landing at the base and taking off. This is NOT typical. It happens only at Christmas.
tl;dr flights to/from GITMO may just be holiday travel