If there is one bar that represents everything great about going out in Key West, it’s Green Parrot. This place has all the Keys nightlife staples: excellent nightly live music, a wooden interior that’ll make you feel a little like a pirate, and bar seating that makes it easy to befriend strangers. It's a well-deserved classic, and is just as fun at 2pm as it is at 2am. The building has been standing since the late 1800s and if you’d like to know what the scene looks like before you go, they have a live webcam streaming all day, every day.