The Great Winter Road Trip of 2009-2010

I’m graduating in a few weeks. I’m working full-time but the university is closed the week between Christmas and New Year’s, and it’s a paid holiday (did I mention that I love my job?). I have Red Roof Inn free nights that are expiring soon. These three facts taken together suggest “winter road trip” to me. But I can’t quite decide where to go.

My inclination is almost always to head north, and the Philadelphia and DC areas are among the most enticing destinations right now. Anything much farther north (or more midwestern) brings a bit of a weather threat. In fact, even DC and Philly might pose threats, which is why I’ve also considered pointing the Buick southward. That would sort of limit me to some combination of Atlanta, Tampa, and maybe Jacksonville or Miami, since I’m not feeling New Orleans and since I’m only interested in urban destinations (which pretty much rules out the rest of the Southeast). Florida is tempting, since I haven’t spent any real time there in almost thirty years, and this is probably the only time of year I could even tolerate being there, weather-wise. It might be a nice change of pace; as I remember Florida’s biggest cities (Orlando doesn’t qualify under my definition of “urban”), they had a rather dense, mildly gritty urban feel that set them apart from the rest of the region–not like the Northeast, really, but more like California, without that unfinished, semi-rural quality so many Southeastern cities have.

That said, part of me still leans to northward because I want to use those freebies in the most expensive areas possible.

Yeah, I know. This is the kind of dilemma lots of people would love to be facing right now. And it’s not really causing me stress. I’m just sort of thinking  out loud rather than specifically soliciting suggestions. But if any of you feel strongly about anyplace (and have some specific reasons), I’ll listen.