I’m new here so please be patient with me if this is the wrong forum to post this in.

Since you say you're new, does that mean just new to TER or new to P4P in general. The reason I ask is that most will tell you setting up a long arrangement, even over night (or even multi hour) with someone you don't already know is very risky. Personality will play a large role, as will expectations regarding rules.

wow that is an amazing fantasy but i have to agree with 36363 in his advice. Imagine all the things that can wrong with a blind date even if just on a repeat, On a vacation you are stuck and both may be very unhappy so his advice of finding 'the one' for you will depend on what you have established as you moved from one hour session to more time together. A simple shopping date at the mall or an afternoon out in public might be as much of a test as your first romp in the sheets. It would be eye opening to say the least and she has to like you too !!

I love fantasy & fetish fun!

Thanks for the advice. Yes I am brand new to P4P. Complete newbie haha. I’ll definitely do what you suggested and then go from there!

Don’t we all haha

Even though you're a newbie. Read their amazing  reviewes . The only  difficulty I would have is choosing which one.
I woud be more worried about the other  male who you don't  know much about.  
You did not mention any compensation for the lucky lady, or if the vacation is compensation. Will you take her on shopping sprees - what's  in it for her otherwise. Those are the things you need to figure out, but finding a lady is not that difficult.    

I am honestly not trying to be condescending here.  

agree with all the other advice here including this that you need some cuck experience before trying this in such a situation where things could go wrong out on some uncharted island where you are on vacation.

as the fantasy  continues on this thread.....I am not going to hold my breath on that

Why would you want to be the only person in the room that has no history with the other three?  The nefarious possibilities far outweigh the positive potential, IMO.  

Might want to see what you can arrange over on fetlife.

I've no doubt, that she'd be successful in picking up a guy/guys at some bar.  

Many years ago I knew a lady who's SO liked to watch and she always asked guys she was hooking up with the go to her place so he could. But the guy had a nick name of "hatchet man" as he supposedly got upset with someone and chased him around with a hatchet.

Did she have an uncharge for the hatchet thing?

LOL

He went full Raskolnikov? Damn.