re: How much cash do you travel with overseas?

Domestic travel only around three or four hundred-ish, but plenty of fives & tens for tips.

Foreign travel (Europe), usually more (€ 1,000 or £600) but again I get a bunch of small denomination bills.

I have my bank get it for me a couple of days before I leave, they'll do it fairly cheaply.

Going to the Caribbean or Latin America I just bring good old American money but usually pre-pay and then credit card pay for accommodations.