3 days or more, most involving flights, but a few were road trips.
They were all with gals I had already known pretty well, and for the most part they all went very well. We managed to bump uglies at least once a day, and for me that is enough. I recall only one time when at the very end (It was 5 days.) we weren't even talking to each other, but for the life of me I don't even recall why now. In any case we both got over it soon enough as we still know each other very well. So enjoyThrew this out in the Florida board and got some great suggestions. Thought I'd see what the rest of the world has to say:
Thought I would start up a little conversation about vacations. I'm looking to take someone on a trip with my at the end of next month. One of my favorite naughty friends has already agreed to go with me but this is a new adventure for me. With that in mind I was curious if anyone has thoughts on the subject of traveling with a provider. Ladies, have you been on a trip with any gentlemen? If so where and anything special you can disclose that happened? Also for the other guys out here have you ever had a provider accompany you on a vacation before? Any do's or dont's you could share?
... 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.
The other thing I recommend is treat your vacation companion as a good friend and not a provider. For example, be considerate of her need for sleep. I went so far as to get a room with two beds. She was blown away by that and years later still mentions it and tells her friends about it. And she showed her appreciation during the trip. 
As was mentioned on a thread on overnights not long ago, don't discuss beforehand "how many times we'll have sex". If you trust each other and enjoy each other's company, that will flow naturally from your time together. Just have fun together, bask in having so much time alone with one of your fav naughty friends, and be considerate of her and you'll have a great time.
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.
They were all with gals I had already known pretty well, and for the most part they all went very well.
We managed to bump uglies at least once a day, and for me that is enough.
I recall only one time when at the very end (It was 5 days.) we weren't even talking to each other, but for the life of me I don't even recall why now. In any case we both got over it soon enough as we still know each other very well.
So enjoy
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
Overall though, I have had a great time with the vacations I have taken via the P4P route, and thinking about it my worst trip I was NOT paying her, so although she was a hooker it was not a P4P date, maybe it would have been better if it had been.
I do agree that managing expectations is important especially where matters about sex and sleep are concerned. I don't expect non stop sex, but once a day won't cut it either. Twice a day and I am a happy camper, as for sleeping arrangements, I would NEVER get separate beds, much less separate rooms, but that is just me. Unlike some guys here I actually enjoy sleeping with a woman and even waking up together seems to add intimacy to the occasion.
... 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.
And even if there's two beds or two rooms, nothing prevents sharing one bed if both want that.
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?
It's all about you and what you want, as the paying customer. Roger wilco.
If I can make my naughty vacation partner happier by ensuring her a few hours of uninterrupted sleep each night, I'm glad to do that. Anyway, I want her well-rested. 
Plenty of time for fun in one bed before and after slumberland.
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?
Some people don't sleep well with a stranger in the bed next to them, others have no problem with it. I don't want to have to make my vacation partner happy (that I am paying) by subordinating my wishes, it's just MUCH easier to find someone who I am more compatible with.
... exactly as you want it, when you want it is ideal.
But there's other things that are more important to me than whether she would rather have her own bed while sleeping. Like, everything she does while she's awake and how compatible we are while awake.
She didn't demand or even ask for separate beds, just told me she needed a good night's sleep. But when she saw them she was very appreciative. I didn't think of it as subordinating my wishes, but as doing something nice for another person
but speaking strictly for myself, that would NOT have been an acceptable arrangement.
but also as you already know, we are two VERY different people.
I hate to be away from home or office for that long.
What a bummer that a trip to the nicest spot on Earth was spoiled.
Come to think of it, the one trip I had where we ended up not talking was also one of the longest ones, 5 days. I think 4 days is the cut-off.
Maybe the best vacation is one where you see a new gal each night, or at least have a rotation of three or four. Anyone ever do that
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 yes I think five days is at least two days too long, my cut off is more like two days now.
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.
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.
Most of my trips are a LOT of togetherness, which might be why only two days or so is about my limit. I think you may be grateful that you both have some time apart during your trip, there is definitely a such a thing as "too much" togetherness.
...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.
As for sleeping arrangements I do prefer to be close like Ga G. Think I'll give the option but if trouble ensues with just 1 bed then we can always request a few extra pillows from housekeeping. They can be used to make a wall down the middle of the bed. At least it works at home for the mrs.