It is early morning. I am dozing on a hammock strung between two palm trees, their fronds rustling as the night breeze disappears into the soft, still humidity of first light. Beyond me is an endless stretch of blue-green water peppered with little islands of mangroves. I hear the soft scrape of an attendant gently raking the white sand beach into swirling patterns, erasing yesterday’s footsteps. I spot a great white heron at the boat dock, poised on one leg and peering into the water for its first catch of the day.

This is not some exotic Caribbean island, and I didn’t need a passport to get here. Instead, with my car’s moonroof wide open under the summer sun, I sped down U.S. Route 1 for adventure and relaxation at the southernmost tip of the nation—the Florida Keys.

Connected by one of the country’s most scenic highways, these hundreds of little islands trailing off the mainland 180 miles into the Gulf of Mexico begin at a river of grass and end in the ocean. Here, American individualism and Caribbean devil-may-care style mingle in a land of Bermuda shorts, flip-flops, tropical cocktails, conch fritters, and lots of Cuban flair.

The Upper Keys: serenity and snorkeling

Because the Keys are made of limestone and offshore reefs prevent the ocean waves from forming beaches here, the Keys don’t have any natural sand beaches. Instead, the shoreline drops off into water that is among the most colorful in the continental United States, ranging from sea green to royal blue.

The beach where I spent my lazy morning is man-made, courtesy of the staff at Kona Kai Resort and Gallery, a Key Largo retreat on Florida Bay that offers a tropical garden escape. With lounge chairs under umbrellas, a pool kept warm by the sun’s rays, paddleboats and kayaks, and an international art gallery, Kona Kai is the place for people who want first-class luxury but, as owner Joe Harris says, “still want to walk around in shorts and a T-shirt.” 

That pretty much sums up not just Kona Kai, but the Keys themselves. It doesn’t take long for the laid-back style to sink in.

That doesn’t mean one has to go without adventure. “The water here is magnificent,” says Harris, “and the diving is incredible.” I took Harris’ advice and arranged for an evening ecotour of the Everglades National Park with Caribbean Watersports.

Captain Duane McCullough guided the soft-bottomed electric powerboat through the shallow 50-mile-wide river of grass. We wove in and out of hidden creeks between red, black, and white mangroves and examined horseshoe crabs, sea horses, hermit crabs, and needle fish from the bay.

Caribbean Watersports also offers snorkeling trips to John Pennekamp Coral Reef State Park, the only living coral reef in the United States. Snorkelers can explore the reef and its many undersea life forms, such as brain coral, purple sea fans, nurse sharks, barracudas, angel fish, and blue parrot fish. Snorkeling guides were quick to advise us to look, not touch. Beautiful and massive, the reef and lovely sea grasses are fragile, and their greatest enemy is man. 

Middle and Lower Keys: bridges, vistas, and wildlife

More subdued and less developed than the Upper Keys, the Middle Keys are known for long watery vistas and endless bridges that represent man’s efforts to tame these islands. One of the Keys’ major man-made attractions is the Seven Mile Bridge, which spans mileposts 40 through 47. Completed in 1911 under the direction of railroad tycoon Henry Flagler, this bridge has withstood hurricane-force winds for almost a century. While visitors no longer can Key hop via this bridge, they can drive it to historic Pigeon Key, a 4-acre island that once served as the railroad bridge’s work camp.

The Keys’ natural wonders—such as its wildlife—are marvelous. At Grassy Key, just a few miles north of Seven Mile Bridge, the Dolphin Research Center (DRC) gave me my first opportunity to swim with a pair of Atlantic bottlenose dolphins. Expertly trained, my two smooth-skinned dolphin friends clicked and chattered as they shook hands (or fins) with me, imitated all my dance moves in the water, and closed our play session with a kiss on my cheek.

Just down the road from the DRC lives another native species of these islands—the Key deer, which stands no more than 2 1¼2 feet tall. The National Key Deer Refuge, located on Big Pine Key, protects approximately 800 of these diminutive endangered species. High fences and large yellow flashing signs along the road warn motorists to drive with caution through the Key deer’s habitat. Despite these efforts, 70 percent of Key deer deaths are caused by collisions with motor vehicles. 

Key West: living it up in the subtropics

Key West remains the biggest draw in the Keys. With architecture and nightlife to rival New Orleans, Key West is funky, irreverent, and packed with tourists, even in the off-season. 

The center of activity is Duval Street, which runs the length of the island from north to south, replete with wild bars, drag queen joints, bawdy T-shirt shops, upscale boutiques, pastel bed-and-breakfasts, and trendy restaurants. I browsed shops filled with beaded curtains, plastic parrots, tropical sarongs, and platform-style flip-flops, and I felt free because I knew if I wore a bathing suit and a wrap skirt to dinner, nobody would lift an eyebrow.

Later, I made my way to Mallory Square for Key West’s nightly Sunset Celebration. Locals and tourists gather here each evening to watch the incredible sometimes-silver, sometimes-orange sunsets while enjoying reggae and blues played by street musicians. 

History buffs will be interested in Key West’s number of famous residents, among them author Ernest Hemingway. In the 1920s, Hemingway wrote To Have and Have Not and Death in the Afternoon at his home here, a Spanish Colonial-style house rising out of a lush garden. Another of Key West’s famous temporary residents was President Truman, who spent the winter of 1946 in the first officer’s quarters on the island naval station. The home now is known as the Little White House, also having hosted President Eisenhower and, during the Bay of Pigs incident, President Kennedy—a keen reminder of Key West’s proximity to Cuba.

Cuba is only 90 miles from Key West, closer than Miami. I made the obligatory trek to Southernmost Point, also known as U.S. Route 1’s Milepost 0, which marks the southern end of the continental United States.

If you need a break from the tours, gaiety, and wildness of Key West, take a trip to the island of Dry Tortugas, home of Fort Jefferson, 70 miles west of Key West. The fort is accessible only by seaplane or high-speed catamaran. Fort Jefferson, with walls 50 feet high and 8 feet thick, never saw military action and is best known as home to Union deserters during the Civil War and later to Dr. Samuel Mudd, who was convicted of conspiracy in the assassination of President Lincoln. 

Today visitors can spend an afternoon exploring the fort or snorkeling in the beautiful blue-green waters beyond its walls—a perfect way, I thought, to close my adventure on an isolated stretch of coral Key at the western edge of America’s only subtropical paradise.