Taking my main SB to Hawaii this summer.  She's so excited!  We are planning the trip together.  Here are some guidelines that have paid me dividends when doing this.

I already was clear, her allowance is not going to change but I'm paying for everything.  Cannot stress enough that you have to clarify this in advance!  I have had other SBs that expected a daily rate while I paid for the trip.  Essentially doubling my cost.  If she was taking time off work, I can see giving extra, but she's not.

Who pays for what.  If she wants to go shopping, it's on her dime.  I might, meaning my choice, give her some money to go buy something to wear for me.  I'm already covering flight, hotel, tours, food, drinks, etc.

Sex expectations.  I already told her I do expect us to be intimate at least once a day.  She was more than happy with that.  Sex really isn't an issue with her, but definitely good to cover in advance

Time alone, I already told her I was taking zoom meetings with clients.  So I do want some alone time.  She probably wants to shop or rest or just tan on the beach.

Have an itinerary.  Obviously, it's Hawaii, we have beach days planned.  But have a plan on what to do, ideas for dinners.  If neither of you have been there, look up ideas.  Don't show up and say, 'what do you want to do today?'  Take charge of the relationship.  It will allow you to keep on budget, otherwise she will pick the most expenses restaurants, tours, etc.  Whatever TikTok said was cool.  I started planning and she got mad at me.  Showed me the hotel she liked.  It was on a different island, meaning more flights and $1500 a night.  I told her no, I was not spending that much.  She understood.

Be clear on what this means for the relationship.  Are you boyfriend and girlfriend?  Engaged?  Etc.  Generally, a cute girl will want to brag about her wealthy boyfriend who took her somewhere.  Are you taking pics together?  Posting on social media?  What do you say to people you meet?  What do you say to people who see these pics or know you are on a trip?  Be on the same page.  Her and I have agreed to be boyfriend and girlfriend.  We have told friends/family about one another.  Her mom does not know the age gap, but will when we post pics together in July.  Make sure both of you are very clear here, feelings can get hurt really fast after going on a vacation together.  

On the flip side, if she's trying to be on the downlow, you are not posting pics.  But.... you are together in a vacation area.  What do you do if you run into someone who knows you?  Finds out you were there?  Especially if you do have a Significant Other.  This is a risk you have to consider.

That was why I got into SBs. No luck on a trip ever

Need lots of chemistry with her before considering it.  Imagine being halfway through a week long trip and you are fed up with one another?  We do have that from what I can tell.  But the few moments apart will help as well.  And beach days, we can just layout with umbrella drinks and get to stare at her in a thong bikini.

Looks like you've really thought through this. I tried a weekend trip with a SB years ago and I def did NOT make things clear in advance!  With predictable results.

You said that her allowance is not going to change.  I assume that means you are normally giving her a set amount every week or month.  But what would you recommend for a sugar arrangement based on a ppm gifting protocol?

Hope you have a wonderful, sexy vacation.  Send us details when you can!

... and you've done the critical pre-discussions.  Well done.  

 
I have twice taken an SB for month-long international trips and followed a similar process, mostly successfully.  

 
Scheduling time apart (almost) every day is vital to making this work.  You will both need that. The only ask I have for my SB during alone time is to give me a general idea where she will be and what time we will meet for safety purposes.  

 
I also budget a modest (maybe $100) daily shopping allowance for her and let her know about it. I don't pre-fund her for this. She needs to show me what she wants, and I will (probably) pay (because she WILL try to go over budget: Gucci sunglasses for $575 AUD was a hard "NO." Who the fuck pays that kind of money for sunglasses when they are $12 at Walgreen's?).  

 
The only other "relief valve" I install, especially on a longer (over 10 days) trip is a promise to fly her home early if she's not happy.  Yes, I risk exposure to the cost of last-minute airfare. But I think it gives her a needed sense of control over her experience. So far, none have asked for that.  To be clear, she's the SB and I'm in charge of itinerary, finances, and BCD time. But granting some sense of autonomy to her helps her feel more comfortable with the trip.  

 
One other idea: During my month-long trips I also scheduled some local SB one-off meetups during some of our away-times.  She didn't know, I didn't tell (apologies to Papa Sweet on this. LOL).  The M&G and BCD times in Australia and Chile were off the hook fun.  You may not have the time for this, either to vette and plan ahead, or during your trip.  But there are just a fuck-ton of hot babes in Hawaii, and plenty of them are up for P4P.  

 
Life is good

 
The Cat

Great planning netnoy! You've thought of just about everything. I think I must have a unique SB situation. We have gone on 3 trips so far, longest being 5 days, and have 1-2 more planned this year. We never had any discussions about anything prior to the trips. I think it is because we click so well. Each trip I pay for everything eg travel, hotel , meals incidentals such as music events entry to museums etc. Before the first trip I did tell her that. She must be unique as she never, ever asks for anything in addition eg shopping. She has no expectations, just happy we are taking the trip together. She has zero, and I mean zero gps and she is zero high maintenance. We didn't even discuss how much sex, it just happened naturally and regularly. I do agree with netnoy regarding taking pics. We never discussed that either, we just naturally knew not to post stuff of us together on IG though we both posted pics of ourselves. I'm fine with that and do love to see her pics on IG knowing that I took them. We do share with each other all the pics that we both took. As for if we bumped into others either of us knew, I guess we just assumed we'd say something like they are a friend of ours. I do realize the possibility of this having bumped into a colleague from San Fran when I was in Hong Kong. That kinda blew me away. (I wasn't with anyone). You never know what random things can happen.  I don't even know if her friends know about me though they know she travels with someone. A couple of my close friends know about my relationship (though not that it's a sugar one)and they are not judgy about the age difference. I think I truly have a unique situation. Pity it will never go anywhere beyond this, but such is life.  

I'm with Laertes on this.

And maybe I'm totally wrong, not that a few rules can't come into play.

Why not just bring a lovely girl whom you trust and just see how it goes?

It's what I've done for a least a decade.   Sometimes there are issues (often financial), but they always work themselves out.

And there's always the backup Herb approach and be ready for new opportunities!

Just me...but have a blast!

Here's exactly why.  Last year, I wanted to do a weekend trip with another SB.  We both love wine, so a trip out to wine country together.  

I booked the hotel, we were going to drive together.  Told her I would pick her up if she didn't want to drive to me.  All she had to do was look hot, keep our conversations fun (she's good at that), and we have fun.

A few weeks before she went on the attack.  Her normal ppm would not suffice for a weekend.  She wanted 5x the amount plus shopping money.  I asked if she was missing work?  She wasn't.  Is she cancelling other plans for me?  She wasn't.  Why all of sudden so much more when she's already getting an all expense paid vacation?  She said her time was valuable and it wasn't worth the weekend for only one ppm.

Why does this matter?  2 reasons.  Now imagine having his chat halfway through the trip?  Second, it's a tell that she really only cares about the money and not sugar dating.  Meaning I'm only as good as my $.  I'm not dumb, I know the girls want money.  But I want more than lip service and sex.  

Here are some questions to discuss with her  

1. Is she taking off work?  Not getting paid?  You do need to cover a portion of that for her, discuss that amount.  Lay on the value that she wouldn't get paid on a normal vacation and this one she isn't paying for the trip.

2. Can she actually afford to with you?  Missing income, family or friends time?  this is important.  If she lives with family, how will she explain being gone for a week?  Some parents won't accept 'im going with friends.'

3. Does she expect a larger allowance for her time?  Ask her.  Again. Lay on value that you are already taking her somewhere.

4. What will she do in the time apart and are you paying for it?  Mine told me she would like a massage.  I said I'd pay for it.  So, I'm not giving her money but an even better experience.

5. Your budget your final decision.  I'm spending $10k on this trip already.  If she thinks I'm just a piggy bank I can go alone or change it to Thailand.  I'm not going with her to take an escort.  I'm going to take a girlfriend.

Maybe it's both. LOL  

Glad to hear success stories from your travel. We don't get enough of those.  My (yes, I admit it's) overplanning comes from real-world bad experiences. But I am naturally a minutia-level planner, after spending 40+ years supporting multi-million-dollar deals with Fortune 500 companies and having to travel with Sales Execs who thought a good power-point deck was all they need to close.  LOL  

 
I've found it's usually better to have a plan and able to change it on the fly.  I can still feel my backache from sleeping in my rental car in a hotel parking lot outside of Nashville because I never bothered to check that the NCAA tourney was happening the same week as my critical meetings. (This was pre-Zoom.) There were ZERO hotel rooms open within 30-miles of the city.  

 
Life is good

 
The Cat

With my current SB it's more than 40. I'm OK in public with her but I am sure I'm older than her parents so telling them would bea hard no.

I hear you netnoy. I guess I totally suss out the lady before I offer a trip. By then I've sized up the likelihood of problems regarding logistics. As the gents have said here things can still go awry on the road, especially the first time. Before I ever took my SB on a trip (it was to Coachella) we had many conversations about the trip so I really got a feel about what she wanted. I think my gal is unique, she never expects extra allowance for the trip seeing as I am picking up the tab - and we fly first class and stay at luxury hotels, and that is way, way beyond what she could do on her own dime. I did volunteer to pay her neighbor to dog sit her pooch ($25/day, I can handle that lol) but the beauty about that is she never ever asked me for it or for anything beyond the allowance so I am safe to offer more knowing she will not take advantage of it. In fact one thing I love about that is I can see she needs something and just offer it and she is sooo grateful. It's a lovely thing. I guess we both really trust each other and know we will always look out for each others interests. I always pick the hotel as I know way more about which ones to pick than she does. I always have her pick the restaurants because she is way better at finding great ones than I am. We really do feel like a team. In NY the first theatre  show we went to see was a bust and we left at intermission. She jumped on the internet and found another show we could see the next day. It was a brilliant show. I trust her judgment.  There is no way I would travel with someone if I didn't feel 1000% confident that it would go smoothly. Just aint worth the hassle. I'm so spoiled I don't think I'll find another SB like her. She is a unicorn and I don't say that lightly. But I do understand netnoy's caution and crossing all the Ts. Maybe part of it too is that my SB is 39 and is fiercely independent. Many times she won't take my help even if it's offered. She is a strident feminist and hates the patriarchy, but adores the fact that I treat her like a queen. Go figure. Somehow it all works.

The girl in the thong bikini works. I wanted a private hone with a pool for some nude poolside fun in Palm Desert. Lol

If there's one thing I've learned from anything we seem to do in this 'alternate' world is that luck plays a huge role!   lol

Thinking back over the past many years... think I've taken four or five SB on an extended vacation (a week or more) and if my older-brain recalls the circumstances correctly, they all were 9+/10 experiences.  As I mentioned, the initial one was on a PPM and she decided mid-trip that my 2x ppm wasn't enough, but we negotiated a 3x ppm and she was happy sucking dick (mine!) the remainder of the time.  The others were all on allowances, so the only friction I recall was 'spending money' and as I had already told them I might spring for a gift or two, but not a penny more, that issue disappeared quickly.  Luckily we all seemed to need our "quiet time" apart and that problem never raised  its head.

26 years.  I'm older than her mom.  She's been a bit nervous telling her family.  But her mom knows I'm giving an allowance, so I'm sure she suspects.

As far as in public, and dating, a girl I dated who was half my age said this, "guys her age make it easy for guys our age to date girls her age."

In the end. I don't give a shit what people think of who I date. We are both adults, I'm not chasing high school girls.

I don't care what random people think.
But most girls want to (and in a lot of cases need to) have a good relationship with their parents, and if  they get involved it's almost certain to create some friction, and make things uncomfortable for her...

Yes Euro-guy I would definitely say my positive experience with my current SB is pure and total luck. I do not possess any unique skills in picking SBs. My track record of failures attest to that lol.

I think it's just filtering through numbers.  Last summer, I ended it with my main SB of 4 years.  She had become more and more of a problem.  When I ended it, she went nuclear.  Lots of problems.

So, I went back to looking for a main again.  Weekly dates, great chemistry, great sex.  Long term, someone I can travel with.  I probably spoke to close to 75 different pots.  Went on several dates.  Some I saw multiple times.  This one stuck around and was checking boxes.  I was clear with expectations and so was she.  She knew what I wanted and appreciated I wanted companionship and not an escort.  8 months later, we have done overnights and full say outings.  I want a weekend long date before we do the week long one.  English isn't her first language so it took a bit to get past that.  My Spanish is only so so.  We both decided in December to not just be SDSB and be a relationship.  I still support her.  She is off all sites.  Cutoff other guys she was talking to.  She knows breaking that rule will end it immediately.

The moral here is. If you want a GF to travel with be clear and willing to filter through a lot of flakes