There would be three choices... One just a little evil, and one, well, just totally evil.
Vacation 1.
Companions: Worf, Jadzia Dax, Spock, Leonard McCoy, Tuvoc, Neelix, Odo, Lwaxana Troi, Quark, Data, and Will Riker (Also, Jake Sisko and Nog)
Destination: Disney World!
Reason: Watching the most dry and humorless characters in Star Trek in one of the most fun places in the world, with their natural foils to make the vacation that much more uncomfortable for them and that much more fun for me to watch their reactions. Lwaxana would be double bang for my buck because she would drive Odo AND Riker nuts. (Jake and Nog would go because I think they would love Disney World, and Nog could annoy Quark while Quark was annoying Odo.)
Vacation 2.
Companions: Will Riker, Deanna Troi, Thomas Riker, and Lwaxana Troi (And Quark)
Destination: A 30' X 30' Cage, with three single beds, a toilet, and a replicator that will ONLY make food, beverages, and paper cups and plates. (Quark and I will be outside the cage)
Reason: Well, just to see who kills whom first. (Quark is there not to kill, nor to die, but SOMEONE needs to be taking wagers on who kills whom first. Who better than Quark?)
Vacation 3.
Companions: Number Two, Nurse Chapel, and Lwaxana Troi
Destination: Risa
Reason: Hot, steamy, group sex.