Yes I have done this with a few of my really nice clients and we just have a blast, the only thing I usually ask for is my own separate hotel room, its not because I wouldn't fall asleep with someone, or spend time with them, but usually I literally cannot fall asleep with someone I don't know, or potentially they snore, and if they snore I will want to die and won't really enjoy the vacation. So I always get my own room, plus then you can have some separate time and don't get completely sick of each other.
I know a provider since 2012 and we have a good relationship. Yes I asked her and she said she considers me a friend. We both know each others real life details. So, I'm thinking about taking her on vacation. Maybe Key West or Sedona in winter for a few days. Am I making a really big mistake or not? Have you ever done this?
then you're most likely not ready to be going on vacation with a provider.
Grow a pair and do what you think is best for you.
I wholeheartedly agreed.
If one has to ask mongers about taking a vacation with a provider on a fuck board, the odds are not good. The only time I'd seriously consider if she unsolicitedly brings up the vacation and the allowance.
One of mine asked for an LV handbag for a 3-day Napa Valley and the short trip was totally worth it! 
If you have spent a few overnights with her, a few days is not that big a leap and you should be fine, BUT if you've never been with her more than an hour or two, a "few days" with the wrong person can feel like an eternity.
And yes, I have gone on trips with providers, both with girls I was actually involved with along with others with whom I was still a paying client, most of the trips have been short ones, just a night or two, but I have gone as long as a ten day trip with a hooker GF which turned out to be the LONGEST ten days of my entire life.
Yes, you might have a great time, but it helps if you have things in common besides fucking. The longer you spend together the more important those common interests seem to be, after all you can fuck all night, I don't know about you, but I am way past the age where I can fuck all week. lol
Are you a beer and pizza kind of guy? If so the artsy scene in Sedona with a girl who prefers Champagne brunches and art galleries might not be a good match. OR Are you the kind of guy who loves "culture" and is she the chicken wings and a football game at the local sports bar kind of girl? I am sure you get the point by now. If you don't really know what she likes, you might want to bring up the subject of "what do you like to do on vacation?" to her and see if her answers align with your own interests.
Go for it !, you've known her for 8 years so there should be no major surprises. You probably have had to excuse yourself, in her presence to
go to the bathroom. You probably have even farted in each others presence. And there certainly aren't any anatomical
surprises (like a cleverly concealed penis) to worry about.
I did it once with someone I knew for about 8 years or so and it was a fun 3 days. My only advice would be make it a
a couple of days or a long week end. I wouldn't do much longer. Remember the old adage about house guests and fish
going bad after 3 or 4 days. It could apply here.
She's still working, so you'll need to agree on a price up front and pay her way.
Yes, there are no out of pocket costs for her, zero. If she wants to charge me a daily rate, that's fine. She has gone "back and forth" on that. She's not going to be my sex slave.... it's probably sex once a day. It's more like (if Key West).... sail boat sunset ride, jet skiing, swimming, just walking around shopping and people watching. She said she once was flown out to Vegas and was told to stay in the room all day which she did. I would consider that rude as hell.
And if it took you eight years to just think about the concept, I'd say you'll probably never be ready. You're making it a bigger deal than it really is
I do suspect that if you had to actually ask her if you are friends then you are most likely very "friendly" but not quite real friends. Do you still have paid sessions with her? If so, then you most definitely need to get the financial details out of the way early so that neither one of you feels "cheated" during or after the trip. You certainly don't want to ruin your relationship with her over a misunderstanding in this regard.
You might also want to discuss how much "togetherness" you each expect, and I don't mean just sex. You might be comfortable spending all day and all night together just like a real couple, OR one of you might need some "me time" during your trip. Once again, if you don't know for sure it's better to ask up front. At least the bar has been set very low, I am sure even at your worst you won't expect her to spend all day in a hotel room by herself. THAT guy sounds like a controlling jerk. It should make it easy for you to look good compared to him. lol
Would you be the first one she would ask to go on her vacation? If the answer is no, then it's a business transaction for her. Don't make her ask for compensation, generously offer her 3 to 5 times your normal arrangement per day.
Now, if you see this vacation as the start of a civie relationship, then offer her even more $$$ to go with you. She will see this might be more than just about her services.
What if he were number 2 on her list of people to go with? Or what if he were number 10 on her list? She might actually enjoy the trip and NOT getting paid means she is not "on the clock" which means she doesn't have to be "on" the whole trip like she would if she was charging for it and this way she can just relax and enjoy the trip without having to worry about keeping her "customer" happy.
And you are even more wrong in your advice if he wants to start something romantic with her, obviously you have never dated any hookers much less been in any LTRs with any women you have met professionally, if he wants something romantic and "real" with her, the LAST thing he should be doing is trying to "buy her love" you can buy her services, but you can NEVER buy a woman's love.
For the record to anyone else who might be reading this, there are some unwritten rules about "dating" or otherwise spending OTC time with hookers. One of those rules is that once you quit paying all dates are "sex optional" for her, she is no more obligated to sleep with you if you are not paying, nor is she obligated to laugh at your jokes, hold your hand or to do anything more sexually than any non hooker you might be taking out on a date. You get to see the "real" person, but be prepared to find out the real woman is much different than the fantasy you have been paying for.
Well not EVERY situation is the same. Have a really good friend thats now happily married to a former long time provider. That relationship started out strictly "transactional"... Then became an "paid arrangement" as he really liked her beyond the client-provider sort of deal.
Some of these ladies at least in his now wife's case had been so used to being "on" working 24/7 mode, had dated MANY interesting people over the years outside of work, and just the toll in general over time emotionally had developed intimacy issues to the point she not necessarily avoided it but became somewhat jaded to everything due to her lifestyle for over 20 years.
Once they got to know one another on a legit level during that arrangement, she opened up more and things just progressed to them being happily married and her deciding it was time to move on.
Now would of things gotten to that level if he didnt "stand out" by taking care of her well for her somewhat exclusivity at that time to get to where they are now? Probably not even though there was physical mutual attraction from her end as well from day one.
Not saying thats something I would personally do as I would actually tend to agree more with GaGa... But again in this sort of situation, every woman.. Or should I say in general PERSON is not a one size fits all deal.
Given you have known her a long time and it appears you both consider each other friends beyond the P4P aspect, you might just try the direct approach.
Why not broach the subject with her and then bound the various ideas around. That might get some early confirmation on the question of having enough to do on vacation together outside the bed to make it work. You might also find, depending on just how long the trip and each of your personalities, that having some options for getting away from one another for an hour or two might be good. I suspect this will not be like some newly wed honeymoon where you cannot stand to be more than 2 feet apart. lol
If so, then go for it.
If not, see how an overnight or even 24 hours goes. If you can stand each other in the morning's light, you can stand just about anything.
I used to do a lot of these, and mostly had a blast.
"Yes, there are no out of pocket costs for her, zero. If she wants to charge me a daily rate, that's fine. She has gone "back and forth" on that. She's not going to be my sex slave.... "
sounds to me like OP is paying. "Back and forth", yeah right?!
If you've had some extended sessions and all was good, try a short vacation -- perhaps a long weekend in Sedona would be a good test.
Given you have an extended history and some kind of a relationship beyond simply transactional, it might work out. The only way to find out is to give it a try, if you're feeling it's worth it.
Buena suerte!
I would love to see a woman's perspective on this. I am in sales and occasionally have to entertain customers. Its work even if I am at a Springsteen concert or sporting event.
I am sure she likes you, but it will still be a work trip.
Now, I would hint at the idea and let her "pitch" it to you. Then you can say, now how would that work...
See what she comes up with. I'd put the ball in her court.
This way she can't complain. Its a WIN WIN.
It really depends on the specifics of your relationship with her (As others have already mentioned). You’ve been seeing her for awhile so I’m assuming there is a connection. My best advice is to just talk with her and be completely open with what you are thinking. The more she knows and the more open you are, the better chance that you’ll have a great time.
For me is a big risk to take many days with a random person. Can be a great sorprise or a complete disaster. So better have some date before to meet each other and see compatibility and if it's work or not.
Better to know everything when you still have time to fix other plan, not during the trip.
Kaly
cuts both ways. I would never consider even booking an overnight with a provider I was seeing for the first time, much less a multi-day vacation. I have vacationed with a few providers, but they are ones I was a regular with for a long time and we were both very comfortable hanging together. In a lo of ways, social time together can be a lot more demanding that sex time.
Have you done a few overnights with her?
Do you have a good chemistry?
If yes on both, then go! Don’t haggle about money ... and have a good time.
No amount of analyzing and planning can eliminate all risks ... just take a plunge and the odds are you two will make good memories out of it.
(Just since you mentioned, I have done a Sedona in winter on such a trip - it was an excellent memory!)
Yes I have done this with a few of my really nice clients and we just have a blast, the only thing I usually ask for is my own separate hotel room, its not because I wouldn't fall asleep with someone, or spend time with them, but usually I literally cannot fall asleep with someone I don't know, or potentially they snore, and if they snore I will want to die and won't really enjoy the vacation. So I always get my own room, plus then you can have some separate time and don't get completely sick of each other.
Is this a precursor to a relationship outside of the hobby, are you looking to keep it professional or just see where it goes?
I do not see a problem as long as you set the ground rules as to fees and expectations. You obviously have a long-standing relationship and enjoy her company. You just do not want to screw up the relationship you have and want to avoid creating expectations. Ask her directly like you asked here. See what she thinks about it and then go from there. Good luck.