Unlocking the Florida Keys

Fuel-up the tank, let your hair down and take a laid-back road trip through America’s own tropical islands in the sun: the Florida Keys. Cruising through palm tree-lined islands and over bridges spanning aquamarine waters, the entire drive along US Route 1 (also known as the Overseas Highway) is freewheeling and breezy, with numerous stops for nature walks, sport fishing, snorkeling and island-inspired seafood cuisine.

Key Largo

After crossing Jewfish Creek Bridge from Florida City, you are officially on the first island of the Keys. The prime attraction here is snorkeling or scuba diving at John Pennekamp Coral Reef State Park, which allows for an up-close look at its famous underwater bronze statue, Christ of the Deep, a 9-foot-tall work of art that was submerged in 1965 by the Underwater Society of America.

Afterward, watch the sun go down with a fresh key lime rum punch in hand at the historic Caribbean Club’s quiet bayside dock (the bar opened in 1938 and was featured in the classic Humphrey Bogart–Lauren Bacall film Key Largo). Then settle in for a dinner of fresh-from-the-boat grouper at Jimmy Johnson’s Big Chill restaurant, owned by the legendary collegiate and NFL coach. Overnight at Baker’s Cay Resort for its boutique feel and inviting nature trails.

Islamorada

From Key Largo, a drive of approximately 17 miles (you’ll pass a giant fiberglass lobster at Rain Barrel Artisan Village) lands you in Islamorada, which touts itself as the Sport Fishing Capital of the World. Hop a charter boat out of Bud N’ Mary’s marina to chase down high-flying gamefish like tarpon and snook. Back at the dock, order up fresh mahi mahi sandwiches at Lazy Days before visiting Robert “Pasta” Pantaleo’s art gallery to view acrylic artwork teeming with seascapes. Then, cool off in the real thing by plying the placid turquoise waters at Anne’s Beach.

Later, drop in at Lorelei’s Restaurant & Cabana to soak up a legendary sunset while sipping a tangy margarita, and then satisfy your hunger at Ziggie and Mad Dog’s with your favorite cut of steak and a dreamy glass of red.

At night’s end, check in to the Cheeca Lodge & Spa, a palm-fringed paradise replete with cascading waterfalls and offering 243 rooms and suites overlooking white sands and azure waters. If you’re on a budget, rest your head at the bungalow-style Blue Fin Inn, a classic motel equipped with kitchenettes situated in the center of town.

Key West

Drive south for 81 miles, crossing over the famous Seven Mile Bridge, to reach Key West, and the southernmost point in the contiguous US. The Conch Republic bustles with colorful characters and eclectic attractions.

Rent a bike and cruise through the 4.2-square-mile island’s winding, flower-lined streets, stopping to tour Ernest Hemingway’s house or the trove of recovered sunken treasure at the Mel Fisher Maritime Museum.

Grab a cold one and overhear fish stories at Hemingway’s favorite bar, Captain Tony’s Saloon (called Sloppy Joe’s in Hemingway’s day), and then meander through wild and vibrant Duval Street, lined with boisterous bars spilling out revelers.

At sundown, stroll the waterfront at Mallory Square to experience the circus-like atmosphere of stunts by street performers, and keep an eye out for the elusive green flash at sunset, a magical moment when the sun dips and exudes a greenish hue on clear, cloudless days. Rest up at The Marker Key West Harbor Resort in rooms brimming with world-class comfort, highlighted during the day by sunlit verandas.

There are endless ways to explore the Florida Keys’ hundreds of individual islands. While it’s only about a 100-mile drive from Key Largo to Key West, set aside a week for a leisurely trip.