Threw this out in the Florida board and got some great suggestions. Thought I'd see what the rest of the world has to say:

... the most important thing, which is to do this only with someone you know well, really like spending time with (NOT just having sex with), and--critical--trust.  

Great feedback! I have been thinking of the sleeping arrangements. Currently one bed reserved but was going to ask what her preference is. Since it will be 5 nights I think I will go ahead and change that. What's the worst that can happen.... she elects not to use it and we are stuck in something smaller than a King 😄 All kidding aside, thanks for the comments!

3 days or more, most involving flights, but a few were road trips.

but I find that about 2-3 days seems to be about my limit. My very worst trip was a ten day trip to Hawaii with a hooker that I had been dating for a couple of months, but who I had never spent more than an overnight with. It was absolutely excruciating and the longest ten days I had ever spent, I found myself wishing that I was paying her so I could put her on the next plane back to the mainland. lol

... like sleeping in the same bed with a woman. I know I do. But I think it's a good idea to ask your vacation partner what she prefers and give her the option of separate beds or even rooms if that's what makes her comfortable. Who knows, maybe she snores big-time, or the guy does, so separation during sleep time is the considerate way to go.

I hate to be away from home or office for that long.

but if you did, that would describe almost every trip I made to Costa Rica until I got "old" of course. Now it's more like one chica each day, and a different one each night, with the "evening chica" usually staying until morning.

and if I am paying someone to be with me, separate beds are simply NOT an option. If it makes her uncomfortable I certainly understand and will find someone else to join me. See how easy that is? Why would I want to spend thousands of dollars on a vacation and not get exactly what I want?

For your trips were you generally together the whole time? This is semi business for me. I will be playing golf most mornings and at an event 3 hours each evening. Kinda bummed we won't have more time together but maybe it's for the best.

It's all about you and what you want, as the paying customer. Roger wilco.  

That particular trip was mercifully broken up by some business I had to attend to while in Hawaii, I had a meeting in Oahu, followed by another on Maui. If we had been stuck together 24/7 I most likely would have put her ass on a plane alone back to the mainland, but keep in mind, she was not "on the clock" Yes, she was a hooker, but as I said we were dating so this was more of a bad BF/GF trip than a hooker/john trip together.

and rather than attempt to "force" a woman to do something she doesn't want to do, which would completely spoil the mood for a multi day trip, isn't it easier, not to mention better for all parties concerned to simply look for a woman who ENJOYS the same thing/s as you?

...you'd be better off finding some local talent rather than bringing someone with you.  And she might want to fill some of her free time with a few appointments as well.  Check the local ad boards.

I hear ya BP. She has been given the option to come to the event as well. It's in the convention area of the hotel we are staying. Think she's looking to get away as she was also very fair with the rate. Probably would cost more overall trying the locals and not sure what kind of trouble that could be. Besides I quite enjoy her company.  

... exactly as you want it, when you want it is ideal.  

but speaking strictly for myself, that would NOT have been an acceptable arrangement.