When you are sentenced to jail time, but you do not want to cause a disruption in your work life, so you take a vacation that conveniently overlaps with your jail sentence.
"How was your weekend Johnson?"
"Uhhh... let's just say I might need to take a jailcation sometime in the next few weeks."
"Uhhh... let's just say I might need to take a jailcation sometime in the next few weeks."
by Pineapple Hider September 10, 2009