There are tons of places in Florida which may suit you. Saint Augustine may fit the bill, but is quite expensive, and I think you may be limiting yourself by asking about only it. Are you open to other suggestions? Key West, I think, will always be the Florida capital of progressive, liberal, and artsy. The Conch Republic will stand against all comers. Have you ever been? I have extensive knowledge about a large majority of areas in Florida. I've lived here nearly a quarter of a century. Could you please provide more specifics? Such as your price range, distance to beach (or would a lake or river do fine as well?), nightlife or quiet, big city or small town, etc.? Perhaps then I could point you to some opportunities you hadn't thought of yet. I look forward to your reply. Best of luck!