The wraparound street-view balcony at Lookout--on the corner of 16th and Market Streets--is legendary for its people-watching prowess. You'll have the whole Castro spread out below you, and you can sit back and enjoy the view or plan your conquests for the evening. The bar itself is pretty standard, but it's the young energetic crowd that makes this a place to be. Monday night is a pretty happening karaoke, and Sunday afternoons they host Jock, where you'll find a bevy of handsome rugby players drinking after a game. Cover is usually $2.

lookoutsf.com