I'm just throwing in a couple more to add to Jim's suggestions. The Condado Plaza has a really nice casino, rooms are nice too, and has a good bar. I wish I could remember the name of the restaurant we went to, but it's been too long ago, it was near Old San Juan, but in a high rise and you could see the inlet from there. Old San Juan is a ball, but watch out for the taxis as you're walking, they drive on the sidewalks. No brakes, just horns.