New Orleans, Louisiana
I just got back, and let me tell you, I'm head over heels in love with New Orleans, Louisiana. Where do I start? The French Quarter and its Creole-style architecture are lively and unique. The jazz scene is robust (try the Spotted Cat when seeking a jazz-filled night out). And the food... the food is marvelous: You need to get beignets at Cafe du Monde, Israeli-meets-New-Orleans-Cuisine at Shaya (order the Fried Chicken Hummus), and Bread Pudding at Creole restaurant, Commander's Palace.
Stay at Hotel Peter & Paul. It's a hyper-unique stay where you can expect to spend the night, depending on your room number, in a former rectory, church, schoolhouse, or convent (make sure to pop into the ground floor boutique, Iris — I bought red sunglasses here and am living for them, sun or no sun).
[Photo via Hotel Peter & Paul]