I loooove travel! [And so many interesting stories posted by so many interesting people.] I think the biggest question to ask yourself before planning a trip is, 'what do I care to do most while away?' If it's explore ruins, amazing modern architecture and museums, then head to Europe. If it's relax all day with books, sand, surf and cool breezes then head somewhere warm. If it's to discover a new culture, cuisine etc then go somewhere you've never been before. Or maybe find an eco-lodge or spa within your budget?
I had a lovely trip to New Orleans solo (pre Katrina but post 911). It was beautiful, relaxing, 4 star hotel next to French Q etc. I had read up on places to go/avoid. I loved the French Quarter and Garden District, signed up for a historic walking tour, and got my palm read in Jackson Square, went to flea markets, etc. And I always bring my camera, but I didn't for this trip for some reason. Oh well, the memories are with me still! =D