So, I read it over and over in SBs profiles. Travel to you/travel with you.

First, I have heard many horror stories given traveling with someone is not exactly the same as spending a few hours with someone. All too often, travel stories are filled with misunderstandings of who pays for what and all other "expectations".

Second, the airline conundrum. While no concrete plans have been finalized, flying seems like it's going to become very labor-intensive.

Thirdly, Why would I do this or incur the additional expense? No offense to anyone who likes to or wants to do this but there is always the opportunity to meet women just about anywhere...either organically or from a business standpoint. I guess if I really, really liked someone, maybe I would go to the trouble but...probably not.

OK. Let me have it.

Back in the day when I spent half my life on a fucking airplane could even see flying "to" an SB, if of course she was in a city I was planning on visiting anyhow, but the very idea of flying an SB "to me" is just plain dumb, so yeah you got it right. lol

 
Actually I have taken very few trips with GF's, hookers or SB's, I agree with the concept that there is "always the opportunity to meet women just about anywhere" whether they be hookers, local SB's or even the hot chick you meet in the airport bar or local pub, half the people on this planet are women afterall. lol

 
Back to FMTY (Fly me to you) whether it's a hooker or an SB, I just don't get the concept and unless it was someone I already knew. I used to fly a girl from Atlanta to Oklahoma about once a month when I lived there, but we had been seeing each other for quite some time before I moved from Atlanta to Oklahoma, and yes I have flown other GF's to see me over the years, but NEVER have I, and NEVER will I even consider the idea of flying a POT SB to come see me at my expense. NEVER!!!

 
BTW as far as bringing an SB with me on a trip, a lot of it depends on where we are going. I have had countless girls ask me to take them to Costa Rica with me when I was going there once or twice a month, but why in the world would I bring my own sand to the beach? lol

Pre-world lockdown I traveled 30-40% of the year, mostly international for the last 25 years. There was only one SB I flew to me or flew anywhere with. We had been together 6 months the first time I had her come to me and it was when I was traveling to NY for business (I reimbursed her after she arrived). A few months later we took our first trip together to London (we both love plays) and later took her to Japan.  

It requires trust. I’m taking care of the flights and sometimes pre-booking excursions where all parties need to be registered so the sb needs to share personal information (real full name, DOB and passport number at a minimum) to get these booked. I also need to trust that she will actually travel and not come up with a lame excuse shortly before the trip and that she is going to give quality BCD to make it worth while.  

Don’t regret the one sb I took on trips, she was more fun than the gf’s! But not going to do this for most.

Have had some sb’s ask me to take them on trips and give them the money to book flights but that’s never going to happen.

...so let's break it down:  
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1. Many SB's who list travel in their profile are not serious. They do it to look more "datable" to an older guy who travels often for fun and business. But a 20-ish college student working a minimum wage job will never have the freedom to just leave town for a week, let alone a month or more. Consider that time with you for travel is in addition to time she may also spend on family vacations or travel with friends. Still, a 2-3 day weekend trip is more possible, but there are lots of caveats to note before you book.  
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2. Booking travel, even overnight in a nearby city too early in the arrangement is a bad idea. You really don't know if you've seen her true BSC come out yet, even if she's stayed overnight with you. So sure, test first with a day trip for wine tasting, a concert, sightseeing, etc. Then suggest a short flight (max 40 minutes in the air) and a hotel overnight. But I wouldn't even suggest it until you are really comfortable with the idea of spending 24-28 hours together - and I mean within 2 to 10 feet of each other - sharing a car, room, bed (sleeping) and a bathroom!  
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3. Negotiating for shared expenses is a bad idea. If she can't afford to go there without Daddy, she can't afford her share of the mutual expenses. So if you want to do this, and expect her to show up, be happy and put out, you'd be better off telling her you're picking up the tab. Yes, put limits on stupid shit if needed - she doesn't need that $500 pair of Gucci sunglasses! (Yes, that happened to me). You don't want to be on the road expecting her to pay her way,  But look at what this really means to your budget. The only extra costs you have are for the additional airline seat, food and entry/tickets to any event.  Your costs for hotel and much of your travel don't really increase by having a 2nd person with you.  
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4. Sugar - this one is tricky. If you're in a PPM arrangements and your "meets" are usually 2 to 5 hours, be careful about how you approach this.  She may want an extended hourly rate for each day. So if you pay her $300 for 4-ish hours ($75/hr.) she may expect $1,800 per day ($75 x 24)! That's hooker math, so don't get trapped by that line of thinking.  And even if you come up with a daily rate, that doesn't necessarily mean you get (or want) 24 hours of sex, so price in non-BCD time as well. Next, consider what she may see as opportunity costs (lost pay from taking time off from work, other SD's she may be seeing, etc.). So again, you need to propose this on the value of the trip/experience, and offer her a reasonable amount of sugar as a bonus when you get back.  Example: if you are normally at $300 ppm and it's a three day-two night trip, maybe offer her $800-$1000 when you get back. But save that offer for later in the discussion. If the trip/location/event is something she really wants (like seeing Beyoncé live in NY or Paris), she may just be happy getting a free ride with you. Then you can approach the offer as "I'll replace your lost wages so you don't suffer" rather than "I'll compensate you for your time." As always in negotiations, you establish the VALUE to her, rather than an acceptable price.  
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Practical issues:  
1. Real names:  If you book the airfare, you're going to need her real ID info: name, DOB at the minimum. If it's international, you'll need passport info as well and will have to investigate Visa rules for the countries you're going to visit.  If you don't want, or she won't give you real ID info, then she will need to book. This is tricky. DO NOT give her cash to buy a plane ticket and reserve a room. It will disappear. You can have  her book out of pocket, provide you receipts and then reimburse her. But most SB's will not have the means to pay up front - no credit card, no cash, etc. So you probably need to have mutual trust to be comfortable exchanging driver's license (and passport) info.  I've always insisted on booking myself. I'm good at and she may not know enough to avoid the problems associated with travel - poor flights/seating/connections, how to get to/from an airport, how to get a good room for minimum dollars.  Imagine how pissed you will be if you land and find out she's not going to be there for another 5 hours.  
2. Road rules: Traveling together - even with good friends - is stressful. You have to set road rules for your time together and apart. Give permission for each of you to "take a break" from the other for 1 to 3 hours. This means she (or you) can go out to the bar, a shop, a park, the pool, whatever and get some personal time.  BUT - you don't pay for anything she does when away from you.  Next, and this should go without saying - bit say it anyway - no flirting/meeting/exchanging info with other guys.  She's WITH you and you are not paying her to line up extra sugar (or dick!). Other women is totally different. She can always bring a friend to the party - but she can't offer/promise any sugar to the friend.  
3. Deep, mutual trust reduces, but never eliminates risk. Remember that she can, at any time, claim whatever she wants to a fellow guest hotel/airline staff, or LEO.  If she gets pissed at you, or if she's just fucking nuts, she can tell someone anything like she's being forced to have sex with you, you are a drug dealer/murderer, or worse. Obviously, she (probably) cannot prove any claim. But do you want to spend the hours, days, weeks or more defending yourself with local authorities?  
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Those are the basics... test small 1st, then get more ambitious. Value prop vs. price.  Must have deep mutual trust.  
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Life is good.
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The Cat

All good and well-presented information and I need a nap after reading your post.

I'll stick to keeping the sugar local, either at home or on location. (wink)

I took my #1 SB to Las Vegas in January.  My flight and lodging covered.  I flew her out and she stayed with me.  Had one of the best times of my life.  
-Set the agenda ahead of time (my work and gym time vs our meals and entertainment)
-She purchased her ticket and emailed me the flight info (real name).  I reimbursed and put her on my hotel reso (my real name)
-Gave her some spending cash at beginning of trip and paid for all meals and entertainment.  That was it.
-Had sex AM, mid-day and night everyday!
-We are both looking forward to our next trip togehter.

I get tons of requests from women who live in Poland or Philippines or some other far off planet.  When I tell them, sorry, I only date locally, often their reply is, but I'm only a flight away.  Yeah, not gonna happen.

I have actually flown to a city for the sole purpose of meeting some new SBs.  And this happened while I already had a wonderful established local rotation going.  Guess I just felt like some exotic pussy!  I flew to Phoenix and had 2 dates lined up with SBs who agreed to come visit me at my hotel. One of those dates was not very successful, my fault entirely as I was not feeling well.  The other was simply splendid!  She was a gorgeous Asian girl and we really hit it off.  So much so that I flew back to Phoenix a few months later for a repeat.  Tbh, she might better be described as a utr pro than a SB.  But the pussy and price were excellent so who cares.  

As for the extra expense, I have so many free flyer miles accumulated that I can take trips anytime for zero dollars airfare.  I have a long lost SB in San Diego who is asking me to come visit her (and her gf!) and I truly want to do so.  Gotta wait till I feel safe socializing again.