Destination: Key West

Whether it’s your beach bucket or bucket list you’re looking to fill, simply follow these directions for an unparalleled experience: Deplane at MIA (Miami International), slip into flipflops, point your rental car south on Highway 1, then savor one of America’s most breathtaking drives to mile marker 0: Key West. By the time you sidle into Duval Street, you’ll be closer to Havana than Miami, and closer to paradise as well.

The cultural center of the Florida Keys is proud of its end-of-the-road status as the southernmost point in the continental United States. This eccentric, two-by-four-mile, last driveable island in the Florida archipelago, a onetime underwater coral forest risen from the sea, has long served as a haven for authors (Ernest Hemingway, Truman Capote, Tennessee Williams, Thomas McGuane), minstrels (Jimmy Buffett, “Mr. Bojangles” Jerry Jeff Walker) and at least one world leader, President, Harry S. Truman, who wintered here in what came to be known as the Little White House.

While a handful of nonstop flights do exist from Atlanta, Charlotte and Washington, D.C. into tiny EYW (Key West International), a far better option is to deplane at MIA and rent a car for the sheer wonder of the 120-mile drive through the Keys. Built on the remains of Henry Flagler’s Overseas Railroad, Highway 1 offers the unparalleled experience of driving with the Atlantic Ocean on one side and the Gulf of Mexico on the other, especially crossing Seven Mile Bridge, where there’s no land beneath you.

Ready for Margaritaville? Here are 10 popular stops you can walk or bike to in Key West.

Southernmost Point: Let’s start at the end, shall we? This colorful ocean buoy, a favorite for selfies, indeed marks the southernmost point in the continental U.S. On a clear day, you can see Cuba from here.

Mallory Square: This town’s favorite spot to catch fabulous Gulf sunsets also features a lively street scene with buskers, jugglers and magicians. Expect the unexpected here; I once watched a young couple parasail by in full Amish attire. And keep an eye peeled for the elusive “green flash” that occasionally turns the Gulf luminous just seconds after sundown.

Ernest Hemingway House: The author and his second wife Pauline lived in this lovely two-story Spanish Colonial on Whitehead Street for a decade beginning in 1931. It’s here that his fishing buddies, known locally as “the mob,” pinned the Papa nickname on the author. Although Hemingway completed “A Farewell to Arms” and wrote “To Have and Have Not” here, it was his friendship with a local captain that would inspire his 1953 Pulitzer Prize winner, “The Old Man and the Sea.” Speaking of Hemingway, don’t miss his favorite watering hole…

Sloppy Joe’s: This popular bar and live music venue has been the epicenter of free thought and spontaneous dancefloor combustion since 1933. Once at Sloppy Joe’s, just step out the front door onto…

Duval Street: Key West’s main tourist strip, which runs roughly a mile between Mallory Square and the Southernmost Point, constitutes a shopper’s dream and a dieter’s nightmare. The former should check out the upscale apparel at Coach and Evan & Elle; the latter should just keep walking past Croissants de France and Kermit’s Key West Key Lime Shoppe.

Harry Truman’s Little White House: In 1946, POTUS 33 claimed this 1890 former Spanish-American War naval station as his winter White House. Today, it’s a public museum and gift shop. Open daily.

El Siboney: Trust me, walking around Key West, you will acquire a craving for Cuban food. When you do, by all means hasten to this 32-year-old, family-owned diner where the ropa vieja, conch chowder and classic Cuban sandwiches will transport your taste buds across the Straits of Florida. You’re welcome.

Mel Fisher Maritime Museum: In 1622, the 28 ships of the Tierre Firme flotilla left Havana with a New World fortune in silver from Mexico and Peru, gold and emeralds from Colombia and pearls from Venezuela. One day after embarking, the flotilla encountered a hurricane that sent eight of its ships to the bottom of the Florida Straits. In 1985, Indiana-born treasure hunter Mel Fisher discovered the remains of the Nuestra Senora de Atocha, filled with an estimated $450 million in gold, silver and gems. Relive Fisher’s shipwreck of the century through the artifacts at the late captain’s not-for-profit museum. Open daily.

Key West Lighthouse and Keeper’s Quarters: Just steps from Hemingway’s house, this 1848 Navy lighthouse kept many a commercial and military ship a safe distance away from Key West’s treacherous reefs. The view alone is worth the narrow 88-step climb. Open daily.

Thompson Fish House, Turtle Cannery and Kraals: Seems strange today, but Key West was once a major processing and canning center for turtle soup, and hence a mecca for turtle harvesters who ferried their enormous catches to town on their backs. This center of the turtle trade, which virtually disappeared following the Endangered Species Act in 1971, was placed on the National Register of Historic Places in 1994. Open daily.

Photo credits: Daniel Korzeniewski /

Jay MacDonald

Jay MacDonald

Jay MacDonald is an award-winning journalist, author and blogger who incorporates humor and human interest into a broad range of topics. Follow him on Twitter @omnisaurus

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