this topic does come up frequently there, and the general feeling is that - sure, it's great to vacation with a charming sexy gal.  But:  you have to know in advance that you two will be compatible.

So, the rule is to work up slowly.  Start with a one or two hour session.  If that goes well, do a 4-6 hour dinner date.  The next step is an overnight.

If it is still all green lights, then plan a weekend in some enjoyable local.

I do it now and then and mostly it has been very enjoyable.

My main adviso to you is that you should neither expect nor want to spend all the time in the hotel room.  Believe it or not, sex can get boring after a while.  Get out and do fun activites and then have a fun time once or maybe twice a day.

I've been on many vacations with various gentlemen anywhere from 5 days to 16 days. To go away with someone you haven't spent more then two hours with is sheer madness.

You should at least spend a weekend together in your own home town to see what multi day compatibility is. Last thing you need is to find that she's miserable with you once you're already stuck together - or that you can't take several more days with her.

Also keep in mind the stress travel ITSELF will bring out.  If you've already done a lot of multiple overnights, and then travel together only to find she's a poor traveler  - at least you will know her well enough to know how to ease the situation. However, if you don't know her well, and she's freaking out over a lost bag, a canceled flight, a hotel error - things can get really ugly.

Vacations are meant for people who are close, happy and know each other well.

I appreciate the comments. I wanted to clarify that I have known this provider and have seen her for years, just not on extended dates.  

Maybe doing a bit of hobbying with locals as I go along is best. I just hate 1st dates.  lol