1. Yes, usually. Cold fronts do blow through once in a while, but normally, it's nice.
3. Bar hop, Mallory Square, Blonde Giraff for key lime pie, the museums.
Take a look in the Port Chat Section by using the Find feature, in the upper left hand corner and typing in Key West. It will pull up all the posts about Key West. It's a great port for people watching. Walk up and down Duvall Street and you'll see what I mean. Congratulations on your upcoming cruise!