Wherever I've been, I've always felt comfortable and "at home".
Until I went back to visit. So I guess I grew out of each area. St. Augustine in college was difficult for many reasons (going back and forth twice a year, different dorm rooms, different rommates every year) but the location itself made me feel at home despite the small town. I had the fewest friends in Orlando but a group of classmates that fostered the sense of community and purpose. Sarasota is NOT the place I grew up anymore... where the hippies hung out outside the library and smoked pot and the cool people went to the topless beach. Too many high-rise condos and q-tips.
I've been in Jacksonville for 8 years and two months.
It's got the beach, some of the culture I need, hustle and bustle when I want it, quiet spots when I don't. It's a little overly-church focused at times, but I've learned how to shut it out. There are rednecks, society wenches, beach bums, yuppies, football players... you name it, we've got it. I'd like a mass-transit system but the city's just too damn big.
I feel at home near the water.
But then again, I felt really at home when I visited New York, San Francisco, Denmark and Sweden, too... maybe I'm just malleable.
Or maybe I only go places I like.
I think I could live almost anywhere that had sunshine. I have SAD so I must have sun sometimes.
Boston is not my town though.