I've always been partial to Intuit's Quicken, even if the company hasn't always been particularly Mac friendly (although that may not be an issue for you).

Quicken is easy to set up, easy to use and easy to maintain. Set up the spending categories and you can easily surprise yourself at the end of the year. How much did you spend on eating out? Gas? Groceries? Quicken can help you find out.

This is not an evenhanded recommendation though. I haven't used other programs. I dabbled around with Moneydance but not enough to know if it was good or better than Quicken. I'm set in my ways I suppose.

Bottom line, Quicken is a pretty good option IMHO.