If you've read Common Sense and Whiskey – the book, you've read these quotes:
Robert Louis Stevenson: “For my part, I travel not to go anywhere, but to go. I travel for travel’s sake. The great affair is to move.”
Colin Thubron said just about the same thing: “You go because you are still young and crave excitement, the crunch of your boots in the dust; you go because you are old and need to understand something before it’s too late. You go to see what will happen.”
I think they’re both right. You just pick a spot and go.
Here are a couple of tools I use to start the process of deciding where to go:
I like Hipmunk for initial checks of air routes, because it's quick, streamlined and easy. (For air route junkies, there's also AirlineRoute.net.) For example, you don't have to click a button to tell Hipmunk if your flight is one way or round trip. If you don't enter a return date, it figures it out. Smart. Here's my review.
If you search for "(your destination) airport," there's usually a Wikipedia result that will tell you the flights to and from a place. Here's an example of what you can learn from Wikipedia about who flies where from Ashgabat airport.
TripAdvisor. It makes me crazy that they try to keep you on their site and don't link to the hotels they describe. That's nuts. But they've got reviews of hotels in some pretty obscure places.
And check the travel planning resources in the sidebar here on CS&W.