Been thinking of a 5 day vacation with an escort I've seen regularly for several years and with whom I believe I have a very good rapport.  Was curious if anyone has had experience (good or bad) doing something like this, or advice.  Thanks

with a girl a few years ago.  The hard part is delineating time on versus time off.  Even though you've taken her on a perceived vacation, she is still going to want to have time to live her own life.  The key is to establish those times.  If you are able to occupy yourself during her off times, you should be able to have a good time.

I've been fortunate. I've had some really amazing experiences traveling with friends in the hobby. Do it!

I love traveling with my clients! The adventures I've enjoyed were business trips for men. I had from 8-9 a.m. to 5-6 p.m. to myself. Afterwards, we would fool around, have dinner, watch a show or go dancing and of course nibble on one another later.  

a young lady agree to a six day trip with me before she retired from the business.  After meeting regularly for several years, we knew each other quite well and had enough trust built up to make such a trip possible.

I’ve done these with several - not all at once - just one at a time!! 😀😮
I would be glad to try a 5 days or more trip, but, I just can’t fit that in biz/work-wise.
“Good rapport” is a start, but IMHO there has to also be a real “liking,” not a faking relationship (obviously).  For me, it is sometimes blurry if she’s an escort, a friend, a semi-lover etc. or all.
I guess I’ll hafta keep trying until I get it right/understood  
My $.02

NCGent, You've described it perfectly.  And my one concern.  I think I (we) are in the blurry zone you describe which would make this a fantastic time, but I'm not 100% certain.  She's on the opposite coast, so we meet 6-9x a year.  We talk about all sorts of things  - kids, spouses (she's married and hubby supports her "hobby", and we have similar situations regarding kids); artistry, history, culture etc...   She's told me countless times I can email her anytime/as often as I want (I don't - maybe 2x a month at most).  She's told me money is pretty much irrelevant - whatever compensation I feel ok with is fine with her.
I know she's done everything from simple overnights to multiday international trips with other clients.  So why do I feel hesitant?  
(Rhetorical question)

Thanks Marie.  If I can ever get down to your neck of the woods, I'd love to meet you.  You're truly 1 of a kind (the best kind).

For me - can’t speak for anyone else - for me, there are “levels” of TER fiends/ladies.  ~10% are disappointing, ~75% are really-good, ~10% are excellent and ~5% are “I can hardly wait to see her again because we really click mentally, personality-wise, and the sex ain’t all bad” 🙂
(Sorta likewise, my ATF who I saw for 2+ years was (is) 1500 miles away from me)
I once did a 3-day trip with a 10% excellent “level” lady and it was just OK-fine.
IMO, I won’t do a multi-day trip with a non-“can’t wait to see her again....”
Unfortunately, I’m between “can’t wait to see her agains.”  I liew of this I do 2-niters
Again, JMHO

I think some gents spend too much time trying to figure out how much time a gal sound be sleeping, how much time she should be going true an array of things on her "menu", how much time at dinner, whether to "get some" in the early morning, or be pissed if he didn't for it all to be "worth it" to him. You were more concerned about just enjoying the total experience while be mindful of her comfort and wellbeing. Honestly, gentlemen with the mindset of mapping out my sleep time, my intimate time, my alone time, and so forth to make sure he's getting his "money's worth will never be the ones I want to spend a multi day/night date with.  

Many more wonderful escapes with opportunities for desire and intimacy
Flirting voyeur
Awesome memories
Be respectful and engaged
Xo

“If you’re worried/wondering about the lady’s sleep etc., it ain’t fun for either one of you.”  It’s a ‘two-off that line in an movie - something like “if you’re in love you don’t need to say your sorry.”  If you’re ‘having fun and comfortable you don’t hafta think about the agenda/game-plan.”
With my ATF I/we never discussed get-away game-plan - it just flowed - just like all of our few-hour get-together.  I knew how good we had it, but, it’s been awhile and all of this discussion brings back memories....

People like different things!  I couldn’t do a 2-3-4 day get-away w/someone who doessn’t Like what I like and vice versa. Personally, I have limited likes! 🙂 I like my “limitations!”  I ain’t never going skiing, snorkeling, mountain climbing etc.  I also ain’t never going w/o my wine and scotch!  So, a teetotaler,  who wants to go skydiving and I are simply incompatible! 😮
I had a great weekend getaway with a lady who had not really done/liked what I do.  I ain’t about sittin around - I’m all about doing things, and entertainment, and fine dining w/fine wine.  She said I wore her out with non-stop fun - and I ain’t talkin about sex! 😀😮
All this talk makes me start thinkin about my next getaway - I’m over due....

I wanted to take my ATF on a 7 day cruise but my wife said absolutely not.

My condolences Rufus, my condolences - sorry for your ‘loss’
I took a cruise - with a TER lady - it’s a highlite of my life!
Have you considered a divorce? LOL

The expression is "Love means never having to you are sorry". I finally saw the movie after all these years 2-3 weeks ago.  I do have a faint memory of the poster for the movie featuring Allie McGraw and Ryan O'Neil.

I used travel extensively with a former client.  We obv had a great connection and had booked several overnights before hand.  It was truly a win win for both of us!  Key would be making sure you express any concerns, expectations, proposed agenda, etc beforehand so no miscommunication. xx

My favorite trip was with a client visiting from abroad who was coming home to the U.S. and really wanted to do something special.  He read I liked hiking so he let me pick the destination and the itinerary and it was just a complete blast- every day going off on a hike then coming back to the resort to play, dine, hot tub it up, drink, hang out with other couples -- for a first time meeting it was an extraordinary experience.

a very smart man once said. "Ya never know what you're gonna get until you bite into it"...aka, try it (trip).
I had a civvy GF a few years back - we dated casually for a year plus.  We decided to go on a 5-day trip.  By Day Two, we went home - it wasn't even tolerable - drove 4+ hours in total silence.  I'da never thunk it ahead of time.  I never saw her again....
I haven't had a civvy GF since! ROFLOL  "once bitten, always shy..."
I've learned - the hard way - that I can't "extrapolate," meaning, after multiple get-togethers and several over-niters, for me to predict how a 3-4-5 day trip would go, is impossible...

you have done a couple overnights with your regular in the past. A shorter trip like a weekend together would be a good way to see if you "click".  

Good advice.   One thing I know I don't have to worry about is her soliciting additional business.

I have traveled with several of my clients for more than just an over night.  As the lovely ladies above have mentioned those trips can be good or bad.  It depends on your idea of what a vacation is and each person's expectations.  I say go for it after several talks to make sure you re on the same page.

and don't overthink.  You mentioned knowing her for some time and having a good rapport.  I have had great experiences going away and one really bad experience.  What  made the experience bad was how the 3rd say in to a 5 day trip in the Caribbean, he told me he wanted me for himself to be his lover.  Then he became possessive, jelaous and nasty because I told him how much I enjoyed being with him but wasnt able to give him the exclusivity he wanted.   I lost the client over it but  this happens when 2 people arent on the same page.

Thanks to all for your advice.  Trip is set feeling very good about arrangements.  Check back in a couple weeks for the results.

A bit of an extended delay in this report due to the TER shutdown...    we finalized plans. She told me the donation was whatever I felt comfortable giving her.  I flew her first class (she was surprised as we hadn’t discussed this).  
So, flew my lady to our vacation spot, met her at the airport and took her to our hotel.. as it was a cross country trip for her, offered her some private time to relax and unwind, to which she told me “no way - I’m here to enjoy a vacation and see the sights with you!”  That set the tone for the next 3 days.  We had a blast together being tourists all day and lovers all night (and she is insatiable - she was ready and willing every  morning and evening) I had her undivided attention the entire time.  I hated to say goodbye at the end.
The epilogue - several weeks after this vacation, I was in her area and we got together for an evening.  Her first comment to me was “can we do another trip together sometime?”  We’ve now done a total of 3 so far and are planning our 4th later this year.    
She’s intelligent, articulate, beautiful, sexy, and so much fun to be with.  A 1 in a million!

where were the trips to and what sites to see?  I was in school for many years and working internships and other part time jobs but now school is complete.  I am ready to do short weekend three day trips.  I need suggestions so I can mention this to my seasoned gents who can travel anytime they want and have comfortable budgets.

Washington DC, Asheville (Biltmore 1 day, Chimney Rock and parkway 2nd day), Niagara Falls (Canada side).

Iam mostly stuck in the RDU/RTP/NRaleigh area i Absolutely love traveling! Not just local states I love out the country! I love the time spend together! Iam single so I get lonely! Nothing turns me on more then traveling. I love dinner dates! I feel like when I get book for a hour is not enough! I always end up spending a little more time then a hour! I hate being in a rush! So anyone love to travel with a exotic lady IAM HER!!

So happy you found what sounds like the perfect lady for you!

Thanks, but my lady deserves most of the credit for the success of our vacations together.  We have much in common, but she makes things so easy.  She’s beautiful, intelligent, and most importantly honest with me.  That’s the most important aspect of our success.  I know she’ll tell me if she’d rather do something else.   It makes things so much easier, and we truly enjoy each other’s company.  We really are friends.

Once when I first started. It was fun - part was destination, the rest was local. We had one fight. lol!