Went to St. Augustine for a couple of days last week- here's a short food report:
Had dinner at A1A Brewery. Sat on the balcony with a nice view of the water. The calimari appetizer was underfried for my dh's tastes, but he raved about his main dish, seafood paella. My chicken dish was pretty good too. Excellent root beer.
Had breakfast at Old City House Inn & Restaurant (next to Casa Monica). My stuffed French Toast was wonderful; my dh's belgian waffle was cold and had an odd grainy texture.
Had lunch at Milltop Pub (I think?) in St. George area. Avoid anything that is supposed to be fried since they don't have a deep frier; sorry, a hot oven just isn't the same. Otherwise, the food was okay but nothing great.
Had second dinner at Outback Crab Shack. Not affiliated with the steakhouse chain, this was a real find. A bunch of picnic tables on a deck, a mediocre singer crooning Jimmy Buffet tunes, and truly outstanding food. Amazing crab legs, chicken, and burgers. This is about 15 minutes outside of St. Augustine proper; website is below.