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. 22,463) 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 Home (907 Whitehead St., 305/294-1136, daily 9am-5pm, $13), an overgrown mansion on Hwy-A1A, 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 (428 Greene St., originally called Sloppy Joe’s, now known as Captain Tony’s) that still survives, “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 (200 Greene St., daily, $12.50), which displays many millions of dollars worth of jewels, silver, and gold recovered from a pair of 17th-century Spanish shipwrecks.
Key West Practicalities
Amid the tourist clutter, Key West holds a range of fabulous restaurants, enough to suit all tastes and budgets. Capturing the eccentric Key West spirit for over 20 years, kid-friendly Camille’s (1202 Simonton St., 305/296-4811) serves crisp waffles, sandwiches, and delicious dinners every day. For a memorable dinner, Antonia’s (615 Duval St., 305/294-6565) has truly excellent Italian food: great fresh pastas, perfect lasagnas, and awesome grilled meats. But for a real taste of Key West, you can’t beat B.O.’s Fish Wagon (801 Caroline St., 305/294-9272), a ramshackle fish stand a block from the water and three blocks north of Duval—soft-shell crab and oyster po’boys, fresh mahi fish-and-chips, cold beer, and frequent live blues bands make this a great place to soak up Key West’s party-hardy-at-the-end-of-the-world ambience.
The Southernmost Hotel in the USA (1319 Duval St., 305/296-6577, $199 and up) has a poolside bar and AAA-rated rooms. A surprisingly desirable option is the Crowne Plaza (430 Duval St., 305/296-2991, $189 and up), which plasters its chain-hotel name on the facade of the La Concha Hotel, one of Key West’s oldest and largest hotels, but otherwise preserves the historic 1920s character; you can’t get more central than this. There are also many nice old B&Bs around Key West, like the landmark Old Town Manor (511 Eaton St., 305/292-2170, $185 and up), an 1880s Greek Revival mansion with a gorgeous garden.
Key West is the end of the Overseas Highway, but it’s not the end of the sightseeing opportunities, so if you don’t want to turn around and head home just yet, you don’t have to. You can board a sunset cruise, or take a seaplane tour of historic Fort Jefferson, a photogenic 150-year-old fortress and prison located on an island in Dry Tortugas National Park, 68 miles west of Key West. Prisoners held here included the hapless doctor Samuel Mudd, who set the broken leg of Lincoln assassin John Wilkes Booth.