Stretching in a graceful arc from mainland Florida south-west into the Gulf of Mexico, the Florida Keys are connected by the legendary 113-mile-long Overseas Highway, the stage for this laidback 11-day road trip from Art Deco Miami to the sun-and-sand playground of Key West, the southernmost point of the continental United States.
The Overseas Highway, with 42 sea-skimming bridges, offers one of the world’s most remarkable coastal road journeys.
Key Largo’s coral reefs and shipwrecks create superb opportunities for snorkelling, diving and unforgettable marine encounters.
Islamorada charms with sport-fishing heritage, turquoise waters and a relaxed atmosphere perfect for watersports or unwinding.
Duck Key combines tranquil lagoons with nearby conservation centres, from turtle rehabilitation to dolphin research projects.
Key West enchants with pastel houses, lively sunset gatherings, literary landmarks and easy access to coral-rich national parks.
Arrive at Miami Airport, collect your hire car and make your way to Loews Miami Beach, an oceanfront landmark set in the heart of South Beach’s Art Deco district. Stylish and contemporary in design, the hotel offers direct beach access, a palm-fringed pool deck, a choice of acclaimed restaurants and a soothing spa — the ideal place to relax and refresh after your flight.
One of the greatest pleasures of holidaying in the Florida Keys is driving the Overseas Highway, a modern marvel of concrete and steel that connects the Keys through a series of 42 ocean-skimming bridges. Some are so long there are moments you can neither see land ahead of you nor behind you, creating the surreal sensation that you’re driving across the ocean.
The key to enjoying the drive is to take your time, stopping where and when you want to soak up the ever-changing land- and seascapes and get to know the communities that call the Keys home. You may well want to stop in Key Largo, the northernmost of the Keys and around an hour from Miami. It’s especially popular among divers and snorkellers, who come to explore coral-encrusted shipwrecks and see the sunken bronze statue, Christ of the Abyss.
After Key Largo you’ll reach Islamorada and Cheeca Lodge & Spa, where you’ll stay for the next three nights. The hotel boasts a gorgeous stretch of sandy beach as well as three heated pools, a nine-hole golf course and the longest pier in the Florida Keys. Islamorada is known as the sport-fishing capital of the world and you’ll find expert fishing guides ready to lead you across the backcountry’s shallow flats for bonefish, snook and tarpon, or out into the deep blue for grouper and giant tuna. If angling’s not your thing, there are also wonderful opportunities for paddleboarding, kiteboarding, tennis, cycling, shopping and fine dining.
Next is a three-night stay at the tropical Hawks Cay Resort on the small, secluded island of Duck Key. A haven of tranquillity fronted by a glorious natural lagoon, the hotel offers numerous chances to get out on the water to enjoy boating, swimming, snorkelling and other watersports. Should you wish to explore beyond the hotel, nearby Marathon’s Dolphin Research Center and Turtle Hospital are both great examples of the many conservation projects, animal rehabilitation centres and wildlife refuges found throughout the Keys. Also worth a visit is the museum on Pigeon Key, which depicts the life of the men who built the original Overseas Railroad from Miami to Key West at the turn of the 20th century – a remarkable achievement orchestrated by millionaire industrialist Henry Flagler.
The route to Key West includes the undisputed jewel of the Overseas Highway: Seven Mile Bridge. The longest bridge in the Keys is a true engineering marvel and always thrilling to drive across; you may even see fish jumping from the water beside you, racing you on your road trip.
Once across the bridge you’ll find Big Pine and the Lower Keys wilder and more sparsely populated than anywhere else in the island chain. This is one of the best places to spot miniature Key deer, one of the Florida Keys’ most cherished land mammals. But it’s really the marine environment that comes into its own here. Beautiful Bahia Honda State Park invites exploration with its palm-lined beaches and gin-clear waters. From here trips can be arranged to the Looe Key National Marine Sanctuary to snorkel among rainbow-coloured parrotfish, turtles and nurse sharks. Further west still, the Great White Heron National Wildlife Refuge offers rare opportunities to spot dolphins and manatees by kayak or paddleboard.
Eventually the Lower Keys segue into Key West, where you’ll end your adventure with a three-night stay at Ocean Key Resort & Spa, a charming hotel in the heart of Key West’s Old Town. This is the place to really let your hair down, enjoying the fire-eaters, sword-swallowers and musicians that appear daily at sunset at Mallory Square, dining out at seafood restaurants, or sipping cocktails at bars like Sloppy Joe’s and Captain Tony’s Saloon, where Ernest Hemingway used to drink. You can also tour Hemingway’s house and studio, where he completed For Whom the Bell Tolls and A Farewell to Arms, walk to the Little White House, the former vacation home of President Truman, or strike out by seaplane to Dry Tortugas National Park, seven beautiful small islands adrift in the Gulf of Mexico.
Return your hire car at Key West Airport on the final day in time to catch your domestic flight back to the American mainland, where you’ll connect with your international flight home.