I was just there last week. I stayed at the Marriot beachside resort. A Beautiful hotel. Its a couple of miles from Old Town (Duval St)but they have a shuttle. I would stay there again. Places to go: Two Friends restaurant on Front St. for diner, Kelly's on Whitehead for happy hour, Pepe's, and Blue heaven for breakfast, Schooner Wharf bar. Once on Duval St. you can get to all of the points of interest without a problem. The island is only 4mix1 1/2mi. For entertainment I enjoyed Kevins Irish bar try to get there when NY Paulie is performing, right next to them is Sloppy Joes.
Don't forget sunsets and street performers at Mallory square, and photo ops at the farthest point south.
The best thing to do is just go exploring there is a lot to do from bar hopping to fishing, snorkeling, golf.