If you don't have enough faith in the gal to do a multi day session, then you should not be with her.

Hundreds are much easier to handle than a briefcase full of twenties, but for a multi-day date, the stack is still going to get bulky. If that's going to be an awkward exchange, see if she would be interested in an alternative means of payment for some of it, such as Green Dot or a money order (leave the "to" field blank so she can fill it out with her legal name later). Depending on your mutual preferences, you can provide this to her beforehand (essentially functioning as a deposit) or when your vacation starts.

*Most* ladies will ask for at least enough to cover air fare beforehand, and if she doesn't request at least a partial payment/deposit I'd be surprised. But, we're all different. If you do go the deposit/prior payment route, be sure you both agree on what will happen to that money if either of you needs to cancel. Obviously, advance payment will require that you trust her not to take the money and run, but I'd hope you'd already have that with someone you're going to be spending an extended time with!

Have fun.

Im sure she has reviews and you have done your homework..as far as airfare and such, when I have done this, the ticket was booked inmy name and all and half the money was in my hand. The morning of the second day I got my balance..after that, it was so much easier not having to worry about money and such, we both had a great time and now it is a yearly event I look forward too..

That being said,I would assume she expects it in full at the start of the date just as any provider would at the start of any date, no matter how long the date may be.