I would seriously try and find someone who you can see maybe once or twice a month as if you can only do vacations , you may end up with a string of different guys . For me , I wanted an older man who I could get passionate with and that won't happen if you only meet once on vacation.
Again , we are all different and seeing the same guy allows you all to try things .
Are you going to be watching and do you want the cuckold husband scenario?
Not sure where we will end up, we bought some ace of spades temporary tattoos and we are going on a vacation this summer and she is going to wear them at the bar and see what happens. Last year we were in Nassau and she dressed up and went to the bar but wasn't quite ready but her experiences there really made her want to do it again so we will see how it goes