Where are you staying in Jamaica? We stayed at Hedo II. There were a couple of days that my wife was taken by the landscapers there at the resort. Although it wasn't a rape at all... It was a surprise when it happened. And she loved it.
Hedo is what you make of it. You can have wild sex with the people you meet or just enjoy a relaxing holiday in nakedness.
If you want to safe money, bring your own lube and toys, because the ones in the shop are expensive. Also beach shoes are a good idea, there are some sea urchins.
well if it was me I would set some thing up without the wifes knowledge you contct a guy tell him what bar your at have him just start flirting and suducing your wife all the while you act like its just happening
Don't make her do anything she is not in to. sometimes it seems great before you get in to it. Maybe you both enjoy it the whole time even. Maybe even in the long term. Chances are tho, you guys will get in over your head if you do not have clear rules. Rules and clear back up plans you guys can resort to when one feels it's going to fast. You can't hurry your wife in to this.
Read up on serious swinging literature, there is much more research done and much more literature out there. Plenty of good pointers to be found on the subject without the fantasy aspect.