This is mostly a travel question. I'm looking for suggestions of not only where to go for spring break, but also potential things to do there. Since I'm asking on these boards, Cancun isn't really on my list, and I'm fine with many "potential things to do" being food- or culture-related.
Confession: I'm bad at traveling.
What does that mean? Two years ago, I went on a spring break long weekend with three friends to New York. Now, I'm from CT, and I'd already done a lot of the touristy things in NY, and I thought I vaguely knew the city. We stayed at a reasonable hotel in Manhattan and tried to do touristy things;; let's just say that there was a lot of walking around with an iPhone, trying to find things, and trying to find things to do. We stayed in one night playing chess. Which was alright, but not something you'd do in a city that is supposedly very alive.
But there was one gleaming success! I'd looked up Socarrat Paella Bar beforehand, and everyone liked that.
This makes me think that good travels depend on solid plans and good food (and friends, if they're going with you). But it's possible that I /may/ be going alone on this, with, say, $50 budgeted per day for meals/tickets.
I was thinking Chicago, even though Wait Wait is conveniently /not/ taping there during my break (last week of March), or Charleston/somewhere in the southeast. I like dance, concerts, musicals, all sorts of food except steak and large slabs of meat (tasty but not interesting); and I've spent significant time in Seattle, so that's not really a city to visit.
Advice? Suggestions? How to solo? How to plan trips? How to travel? Where to go?