I'm still in the planning stages of trying to decide how much money to bring to CSS. Because I plan on doing a little exploring off the resort and I need to do some tipping I'm bringing a couple of hundred dollars in cash. Of course broken down into 1's, 5's, 10's and a few 20's my question is has anyone ever had a problem going thru airport security both in the states and Jamaica with large amounts of money? I plan on keeping the money in either my purse or my bf wallet I was just wondering has anybody been harassed or questioned for having large amounts of money. LOL I think because my trip is next month I'm becoming a bit paranoid over what could go wrong.