New Orleans may be home to America’s most festive thoroughfare, Bourbon Street, but Key West’s Duval Street is a close second. This two-kilometer-long (1.25-mile-long) road runs from north to south, from one end of the island to the other, and passes through the city’s historic Old Town. It’s lined with bars, restaurants, stores and galleries—many of which are among Key West’s most famous, including Sloppy Joe’s, a Hemingway hangout back in the 1930s and still a hotspot today. By day it’s mostly for shoppers, but it really heats up at night, with huge crowds strolling up and down the street, live music spilling out from the bars and a party atmosphere all around.

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