So, there's a trip I take once a year, plus an extra time every three years for sporting events.  It's a pretty expensive trip (to me), plus a chunk of time off, so I'd like to mitigate a little of that if possible.  

There is no escort advertising there (literally and trust me, none), so the "touring" model doesn't work.

Any other ideas?  Providers and hobbyists.

...and work your ass off and save up for it

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Only one regular is into the sport and of course I tried that ;P

It isn't a matter of technically affording it, I'd just be foolish to spend a few stacks if I was able to make a few instead.

Have you not seen all the dopey johns here that LOVE to take a gal on vacay, watch them read, sleep, shop, shit AND foot the entire bill?

Throw in a blow job or two and you're golden.

Christ, full service will get you your own room.

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Advertise where you generally advertise regarding the trip and see if anyone is interested. Obviously they should have seen you before or at least have a session or two with you before you go with him.

Make it very clear the donation you are expecting is to bear all trip costs and incidentals (or negotiate a per diem rate with some deposit) and in exchange you are going to provide him with the service you are comfortable with (same room, separate room, when to be BCD, etc...)

There might be single men in Chicago who might be interested in spending a few days with you and bear the costs of your T&E. I have not seen such advertisements commonly, but you could become a trendsetter...

Good luck!

and peddle your ass over all the town?

(ba-doom)

But seriously folks:

Here's a useful idea:  If you can't advertise while you are out there, offer the idea to some favorite clients of yours that they accompany you on the trip for a discounted price.

Since you were planning to take the trip anyways, any money you get from them is gravy, and you don't have to worry about screening strangers, etc.

Just a thought.

Since you have already ruled that out. Maybe post an ad in your area of what you’re looking for and see what happens. Of course you would want to meet them before the trip because it  would be crazy for both the provider and client to take an extended vacation without checking for at least some chemistry.  

Screen your potential clients by checking references to see if they have done extended dates, time, and means to do so and not just wasting your time. Once that is done that offer them a free dinner or lunch date to have some conversation and a discounted session but ONLY after you have check their references to make sure this is something they have done before or you will have everyone wanting a free date and discounted session. EX. You don’t want to offer that to a client that only books one hour appointments. You need someone with an extended travel reference to prove they are not time wasters and have the time/means to do so.  

You already have very competitive overnight rates. If you find someone just be willing to negotiate since this is more your idea and they didn’t come to you. Agree on how many and often BCD, separate rooms, same rooms, are you going to spilt the travel cost or is he covering it ect.

Just get a few different packages in your head beforehand and negotiate each one:

Package 1: He covers the trip cost, same room, X amount of BCD for X price

Package 2: Split the trip cost, separate rooms, X amount of BCD for X price

You get the idea….

Who knows like someone else said this could start a trend for providers wanting to travel!!

They can tell you all about it. Perhaps, not the escorting piece.

Here I am! Just ask Dr Who!!

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Are there still travel agents?  Other than corporate?