The Pensblog has started a thread on where the best places to watch Pens games around the world are, with fans posting where they've had success. There are a ton, mostly around Pennsylvania, but here are some places where I know we have readers:
NYC: Foley's Bar (shown).
Jacksonville, FL: Sneakers (Jax Beach especially), Gators Dockside in Baymeadows.
Chicago, IL: The Dark Horse, kitty corner from Wrigley Field. Also Durkin's.
Boston, MA: The Sports Depot
Cleveland, OH: The Winking Lizard in Lakewood (whoop whoop!)
Cincinnati, OH: Martino's on Vine. It's near the University of Cincinnati on Clifton. (whoop whoop -tm)
Rome, Italy: La Botticella. This is where I'm going to be hanging out in the spring!
Hope that helps you Pens fans! I tried to look for Orlando places, but didn't really see anything. But if you have any place, put it here or up on Pensblog!