Conversations about money

This post http://www.getrichslowly.org/blog/2009/02/23/outside-looking-in-how-others-view-our-spending/ gets into discussions with friends about money and the 'you can't have it all' idea.

We have now paid for our Italy trip in full. How do you traveler's decide what to bring for spending/meals/entertainment? Some of our meals and tickets are included in the package, though not all of them are.