Key West · Nightlife

A nightly outdoor arts festival on the square at the north end of Duval — street performers, craft stalls, psychics and food carts — with the crowd building about an hour before sunset. Free to walk into; you pay only for what you buy or tip.

Corner of Whitehead and Southard, one block off Duval, open since 1890 and still the island's serious live-music room — blues, roots and touring bands, with the shutters open onto the street. Locals rate it above anything on Duval. No official site we could load; check their posted calendar at the door.

201 Duval at Greene, trading since 1937 and on the National Register of Historic Places. Open 9am–4am Monday to Saturday and from 10am Sunday, kitchen until 10pm, with live music daily from 10am to 2am. It hosts the Hemingway Look-Alike Contest each July.

428 Greene Street, in an 1851 building that was an icehouse and morgue before it was a bar — and was the original Sloppy Joe's that Hemingway drank in. A tree grows up through the middle of the room and out the roof. Smaller and less of a scrum than its Duval neighbours.

202 William Street on the Historic Harbor Walk at the Key West Seaport, open-air and on the water since 1984, on the old Singleton shrimp factory site. Opens for breakfast at 8am (8:30am Monday to Thursday) and runs live local musicians through the day and evening.