Zeebs - he's now buying you makeup with his former fag money? Not shabby at all. Does he have a brother? *hopeful look*
It's not that difficult to put together a holiday kit, really. First, get thee a few five and ten gram size jars with sifters. Second - save your samples, especially the baggie ones.
I'm lucky that I've got the little brush set that fits in your hand, pretty close to right in your palm (six brushes, enough to cover everything you need on holiday, and they come in a little soft vinyl snap-shut case). Maybe Karen could be persuaded to sell those again....?
Anyway, there's that, and it packs up by itself, and only takes a few inches. Inside the small makeup bag - and it is small - a ten gram jar of foundation. A ten gram jar of Perfecting Powder. A ten gram jar of Datebait. Those are my essentials, your powders may vary, but you really only need foundation and one or two PPs.
Pink Twink and Elle for eye shadows - GWPs are smaller than regular E/S's, and you can use either of those ones as a one-colour wash, or create a nice look with them together. Sample baggies I got of Cougar and Wildcat - I love those two, and Wildcat also makes a great liner colour - plus they're a great combo for evening wear. I cheated and put in Velvet as a second liner/contour colour. But you can use Cougar and Wildcat alone, and sample baggie size is great - we must convince Karen to have another sale on E/S samples, along with the mini-brush sets
Samples of Flirt and Tart Light, my go-with-anything blushes. A sample of Beach Bunny for bronzer. A sample of Crystal Perfecting Glow for highlighting. A mascara. Four lippies - choose your own! Mine are Cherry Crush (red, and can be layered), Ice Princess (my perfect pink, and can be layered), Beloved (looks good with everything on me), and Rare Berry, which is another knock-out colour for me, but it doesn't look obvious - unless I rev it up with Cherry Crush.
So, 3 ten gram jars, 5 five gram jars, 2 three gram jars, 2 tiny plastic baggies, 4 lippies, a mascara, some cotton balls (great for touching up blush or powder when you're out), a few cotton rounds, some q-tips (they sell 30-packs that are really tiny), and a couple of squares of microfibre cloth, about 2x3 inches to wipe off the brushes between applications (you could put those in the pocket of the brush case. And if you wanted, you could throw in a sample size concealer, or brow powder, or both.
It sounds like a lot, but it really takes up next to no space - the makeup bag is about five inches by three inches, just a cheapie I picked up at a chemist shop. Depending on how much makeup you use, it should last you a month or six weeks on holiday.