Closer to Cuba than to the U.S. mainland, and still proudly preserving the anarchic spirit of a place that was founded by pirates, Key West (pop. 25,478) is definitely a world unto itself. The main drag, Duval Street, has been overrun by tacky souvenir shops, but the rest of Key West is still a great place for aimless wandering.
Just a block from the official “Mile Zero” end of US-1, one of Key West’s most popular stops is the Hemingway House (daily 9 am–5 pm; $9), an overgrown mansion on Hwy-A1A at 907 Whitehead Street where the burly writer produced some of his most popular works, including To Have and Have Not and For Whom the Bell Tolls. Writing in a small cabin connected to the main house by a rope bridge, and spending his nights in the roughneck bar (originally called “Sloppy Joe’s,” now known as “Captain Tony’s”) that still survives at 428 Greene Street, “Papa” Hemingway lived in Key West for about 10 years until his divorce in 1940, when he moved to Havana.
A half mile away, at Whitehead and South Streets, a brightly painted buoy marks the “Southernmost Point in the USA”; next to this is the “Southernmost House.” (There’s also a “Southernmost Motel.”)
At the other end of Duval Street, one place you ought to go—especially if you can time it to be there around sunset—is Mallory Square, which faces west across the Gulf of Mexico and the open Caribbean Sea. Street performers juggle and play music on the broad, brick-paved plaza all day and much of the night. This historic waterfront area is lined by old warehouses and the Mel Fisher Maritime Museum (daily; $9), at 200 Greene Street, which displays many millions of dollars worth of jewels, silver, and gold recovered from a pair of 17th-century Spanish shipwrecks.
