Duval Street is loaded with bars touting live music and Sloppy Joe's is my top draw pick. It is a good town to sip and dance into an all-night affair. Try all the places from Mr Z's pizza to the scattering of upscale wine lounges. Be careful which bar you walk into like the Aqua Club, as a Drag Show could be in progress! Plan ahead each day to hit a different happy hour. The seaport is a nice zone where you'll find classic Key West bars that maintain the old island vibe. Have your best drinking game face on as Key West is a party city.