Would you pay upfront for a vacation trip?

[labiologie]

Have a vacation with a provider next month - about a week in a domestic location. I’ve met the provider a handful of times already for a few sessions.

My worry is this: I’m paying him $12k in cash for the trip for his rate. I don’t really want to carry that much cash through TSA and my bank doesn’t have locations where we’re going. I’m thinking about meeting him with the cash a few days before we leave to pay him.

Thoughts on this? Is it a bad idea? I trust the guy, but I’ve never given someone so much money upfront. To be clear, the provider hasn’t ASKED me to pay early. 

Edited Monday at 06:06 PM by labiologie

[mrkileen]

Half upfront, half after?

[+ Vegas_Millennial]

25 minutes ago, labiologie said:

My worry is this: I’m paying him $12k in cash for the trip for his rate. I don’t really want to carry that much cash through TSA...

I carry cash through TSA all the time on that order of magnitude.  It's no big deal.

[labiologie]

Just now, Vegas_Millennial said:

I carry cash through TSA all the time on that order of magnitude.  It's no big deal.

Oh interesting! I was reading and while I know it’s legal, a lot of people were bringing up TSA working with local LEO and civil asset forfeiture. I figured it’s rare but also just have no experience bringing more than a few hundred bucks in cash through.

 

it you do it often that’s definitely a relief.

[+ Vegas_Millennial]

2 minutes ago, labiologie said:

Oh interesting! I was reading and while I know it’s legal, a lot of people were bringing up TSA working with local LEO and civil asset forfeiture. I figured it’s rare but also just have no experience bringing more than a few hundred bucks in cash through.

 

it you do it often that’s definitely a relief.

If traveling internationally, just remember to declare it. 

If traveling domestically, then it's no problem/hassle whatsoever.

Edited Monday at 06:25 PM by Vegas_Millennial

[Mark_fl]

I would discuss with him. Not only would I not want to risk losing that much cash, he might have problems bringing it back.

I'd suggest to him paying half in advance, or paying electronically.  But leave it up to him, so you're not on the hook.

If he wants cash there, give it to him shortly after arrival, so you don't have to worry about it getting stolen or turning up missing. 

Im all for cash only, but Im worried about a much smaller amount given to a provider who will be spending the day roaming around a city before heading home.

[+ glutes]

1 hour ago, mrkileen said:

Half upfront, half after?

1/3 upfront , 1/3 when he shows up, 1/3 at conclusion.

[big-n-tall]

The providers (2 specifically) I see the most and go extended trips with, I have given them their entire rate before the trip. However, I know these guys extremely well and for years (one more than a decade).

As previous posters mentioned, you can carry that amount through tsa or you can give the guy a partial payment now and the rest when you get to your destination.

[soloyo215]

6 hours ago, labiologie said:

Have a vacation with a provider next month - about a week in a domestic location. I’ve met the provider a handful of times already for a few sessions.

My worry is this: I’m paying him $12k in cash for the trip for his rate. I don’t really want to carry that much cash through TSA and my bank doesn’t have locations where we’re going. I’m thinking about meeting him with the cash a few days before we leave to pay him.

Thoughts on this? Is it a bad idea? I trust the guy, but I’ve never given someone so much money upfront. To be clear, the provider hasn’t ASKED me to pay early. 

My two cents, and please keep in mind that I'm talking hypotheticals, as I've never experienced anything remotely close to an entire week with a provider.

I'd give half upfront and the other half at the end. Seems like a good compromise, especially since you know him so there should be a degree of trust in venturing to do that.

Enjoy your time.

[jeezifonly]

It's hard for me to imagine myself vacationing with a provider. Great fantasy fodder, to be sure, but a personal relationship (traveling/motoring/recreating/ dining/convo/+sexymaking, all personal) is taking hold from a professional arrangement without the client even noticing.

Until day four.

[Tallywad]

More than $10,000 you must file FinCEN Form 105 (Report of International Transportation of Currency or Monetary Instruments) with U.S. Customs and Border Protection. Failure to declare amounts over $10,000 can lead to seizure, civil fines, and criminal penalties.  (This answer from A.I.}

[+ JamesB]

2 hours ago, Tallywad said:

More than $10,000 you must file FinCEN Form 105 (Report of International Transportation of Currency or Monetary Instruments) with U.S. Customs and Border Protection. Failure to declare amounts over $10,000 can lead to seizure, civil fines, and criminal penalties.  (This answer from A.I.}

 

The OP is talking about a domestic destination.

[mike carey]

4 hours ago, JamesB said:

 

The OP is talking about a domestic destination.

Yes, he is, and @Vegas_Millennial made that distinction up-thread. To add to the international travel tangent, as well as the US reporting rules, you should check if any international destination has similar reporting rules. As an example, Australia also has a $10k reporting requirement, and that's just under $US7k. In both cases it's perfectly legal to carry more than the reporting limit, but at least in Australia's case if it's not reported the money may be subject to confiscation.

[+ azdr0710]

don't forget to give him three or four hours "off" (away from you - gym, check emails, personal shopping, nap) each day... and some daily walking-around money......

[labiologie]

22 minutes ago, azdr0710 said:

don't forget to give him three or four hours "off" (away from you - gym, check emails, personal shopping, nap) each day... and some daily walking-around money......

I appreciate all the advice yall have given me!

 

I will say the idea of daily “walking around” money made me laugh. I’m paying this man $12k for his time, and paying all expenses. I think he has plenty for “walking around” without me giving him more cash.

Edited yesterday at 04:45 AM by labiologie

[BuffaloKyle]

I know you said your bank does not have locations where you are going but I'd feel more comfortable just paying an out of network ATM fee to get cash out instead of paying all up front. Did you do an ATM search just to see if there is anywhere in network where you can take money out where you are going? You could also purchase some Mastercard/Visa gift cards as well if he'd take that as payment when you arrive at your destination. There's a fee though with them as well.

[+ Pensant]

8 hours ago, BuffaloKyle said:

just paying an out of network ATM fee

If you have a large enough account, with Morgan Stanley for example, your bank will reimburse you for all out of network fees.

[maninsoma]

Does this provider even want that much cash?  Maybe he does, but maybe he'd prefer it to be transferred to him electronically.  I would never do a transfer to someone I didn't know well, but it sounds like you know this guy well so that would be my preferred way to pay as long as the provider agreed.

[jackcali]

9 hours ago, BuffaloKyle said:

I know you said your bank does not have locations where you are going but I'd feel more comfortable just paying an out of network ATM fee to get cash out instead of paying all up front. Did you do an ATM search just to see if there is anywhere in network where you can take money out where you are going? You could also purchase some Mastercard/Visa gift cards as well if he'd take that as payment when you arrive at your destination. There's a fee though with them as well.

An upvote on the ATM suggestion.  I doubt there's a location in the US where you can't access ATMs with your bank card for a fee of a few dollars, for which you get the anonymity and non-trackability of cash payments.  If there's a concern about the provider being stuck with all that cash, then multiple payments both before and after the trip (assuming you can hand him cash) is another way to avoid electronic transfers, if that's your concern.   

I've used Visa or Amex gift cards in the past, but I've had trouble finding a vendor who will sell for cash a prepaid with a large-enough balance.  It must be possible, but I haven't done the legwork to find a source.  

Edited yesterday at 03:38 PM by jackcali
clarity

[Mark_fl]

Isn't there usually a max withdrawal on an ATM? I wouldn't want to risk not paying the provider because of it.

[topunderachiever]

I never thought I'd say this, but write him a check and give it to him the day you depart.  

a) neither of you should be in possession of that much cash...  if you're uncomfortable with loads of cash, shouldn't he be as well?

b) he can e-deposit it on his phone to his bank anytime he wishes and withdraw as he sees fit.

c) if you're doing a trip like this, there better be mutual trust and if so, all will be fine, right?  

d) OR, text him and ask him how HE thinks the fee should be handled.  

[Njguy2]

2 hours ago, Mark_fl said:

Isn't there usually a max withdrawal on an ATM? I wouldn't want to risk not paying the provider because of it.

In the U.S., Financial institutions place limits on daily ATM withdrawals to protect customer accounts from fraudulent activity. Daily ATM withdrawal limits are usually somewhere between $300 and $1,500, but can vary depending on the institution. You can raise your daily withdrawal and purchase limits by contacting your bank.

[+ JamesB]

On 1/26/2026 at 12:54 PM, labiologie said:

Have a vacation with a provider next month - about a week in a domestic location. I’ve met the provider a handful of times already for a few sessions.

My worry is this: I’m paying him $12k in cash for the trip for his rate. I don’t really want to carry that much cash through TSA and my bank doesn’t have locations where we’re going. I’m thinking about meeting him with the cash a few days before we leave to pay him.

Thoughts on this? Is it a bad idea? I trust the guy, but I’ve never given someone so much money upfront. To be clear, the provider hasn’t ASKED me to pay early. 

 

First of all, if he hasn’t asked for it upfront, don’t feel pressured to offer it.

Even when you trust a provider, it’s worth remembering that money has a way of changing behavior. Paying 100% upfront introduces several practical risks. If something happens on his end after the cash has changed hands, illness, a family emergency, or another issue, you have no real leverage to secure a refund or even a reschedule. Also, while most professionals remain professional, full prepayment can sometimes shift the power dynamic or weaken the incentive structure of the arrangement. There’s also risk on your side. If your plans change or an emergency prevents you from going, recovering a large cash amount from an individual can be extremely difficult.

While it is legal to fly domestically with any amount of cash, large sums can attract attention. If TSA encounters a significant amount of cash during a search, they may refer the matter to law enforcement. You could then be asked to demonstrate that the funds are legitimate, which can quickly turn into a major headache and even cause you to miss your flight.

There are safer alternatives. One option is to ask whether he would accept a cashier’s check or certified bank check. It’s safer to carry, widely accepted, and can be canceled if lost. Another option is to offer a partial amount, for example $3,000 to $5,000, a few days in advance as a good-faith security deposit, with the balance paid upon arrival.

[labiologie]

I think I’m going to offer him half a few days before and the other half at the end of our trip! Seems like the best way to do it for me.

[Pd1_jap]

Have fun!