From Miami to Key West, Jenny Southan drives the long highway linking the coral archipelago of the Florida Keys
After an hour of swooping flyovers, the towers of Miami have disappeared behind us and we are cruising down the South Dixie Highway, through the Everglades. A sign warns of crocodiles crossing, and I am sure I see a squashed anaconda glistening by the side of the road.Soon we are entering Key Largo. It’s the first of the Florida Keys, a coral archipelago that stretches more than 100 miles like an unfastened necklace – flat little islands held together by a single strip of tarmac – all the way to Key West. United by turquoise, on one side is the Atlantic, on the other the Gulf of Mexico.
You can’t beat an American road trip, and if you’re in Miami for work, there is no better weekend escape than jumping in a car and cruising down to the most southerly point in the continental US. We pick up our wheels from the Hertz office on Alton Road in South Beach, two cups of strong black coffee sat between us as we pull out of the car park into the morning sun.
Last year, Florida saw a record 105 million international visitors, 1.7 million of them from the UK. I can see the appeal – it’s the Sunshine State, after all. And down in the Keys, it’s a kind of kitsch, palm-strewn paradise.
At 165 miles, the journey can be done in a few hours (the maximum speed limit is 55mph), but the fun comes from pit stops along the way. The 113-mile Overseas Highway takes us past the ramshackle Caribbean Club in Key Largo – the oldest bar in the Upper Keys, dating from the 1930s and popular for daiquiris by the shore – through Plantation Key and down to Robbie’s Marina in Islamorada.
Robbie’s marks the halfway point, about two hours out of Miami, so we slide off the highway into its dusty car park. There are stalls selling tikki mugs and hand-painted surfboards, while down by the water is a wooden jetty lined with motorboats.
We buy a bucket of bait to feed the giant tarpon that congregate below the surface, and soon discover they aren’t the only ones after a snack – all around are bold, orange-beaked pelicans who waddle up to snap the fish straight from our fingers. Feeling peckish ourselves, we eat blackened mahi sandwiches with fries and slaw at the Hungry Tarpon restaurant, under the shade of a tree.
Back on the road, we pass through Long Key, Fat Deer Key and Marathon. We don’t have time to visit the Sunset Grille and Raw Bar but I’m told it offers great views of the Seven Mile Bridge, which we are soon speeding over. It’s magnificent, with nothing but the ocean on either side.
The first sight of land is Little Duck Key, then Missouri and Ohio keys. At this point the highway cuts through Bahia Honda State Park, a square mile of protected coastland on Big Pine where you can swim and snorkel (US$8 per vehicle). In 1935, the Florida Overseas Railroad was hit by a hurricane, and you can see the remains of the Bahia Honda Rail Bridge from the white-sand beach.
After passing through the likes of Cudjoe Key, Sugarloaf and Saddlebunch, the final stretch takes us into Key West for sundown. Only 90 miles from Cuba, the Conch Republic, as it is known, is an island of just five square miles in the Florida Straits. Cruise ships come into port here, bringing hoards of pleasure seekers disembarking in search of Key Lime pie (the best is found at Kermit’s Pie Shoppe at 200 Elizabeth Street) and quirky souvenirs (buy the Donald Trump Presidential Hot Sauce from Peppers of Key West, 602 Greene Street).
The town may be small but there are numerous good hotels, including the Waldorf Astoria Casa Marina and Southernmost Beach resorts. We are staying at the Sunset Key Cottages, part of Starwood’s Luxury Collection, on a nearby private island. Check-in is at the Westin Key West Marina (245 Front Street), and the crossing takes about ten minutes by boat. From a distance, we see crowds gathering on the harbourfront for the daily sunset celebration on Mallory Square.
Winding paths lead us past lush lawns, jasmine and frangipani, swimming pools and pastel-coloured weatherboard bungalows, down to the shore and our home for the night. The luxury resort has 40 one- to four-bedroom cottages, each with wraparound verandas and fresh beach-chic décor.
We sit outside with a cold glass of wine and watch the stars come out, before strolling to Latitudes restaurant for dinner – it’s a magical place with tables on the sand by the sea, and palm trees wound with lights. The American-Caribbean menu includes the likes of grilled jumbo shrimp, seared scallops and butter-poached Florida lobster tail – a well-earned feast after a long drive.
At night, Key West is relatively sleepy, apart from a few bars on Duval Street that draw partygoers with live music, rum and craft beer. The Porch occupies what looks like a haunted house in an overgrown garden, while across the road, lit in red neon, is Sloppy Joe’s saloon, which will host its 36th annual Ernest Hemingway lookalike contest in July. With their Classic Revival timber “Conch” houses, a style developed by 19th-century Bahamian immigrants, the side streets are so pristine, they look like they are part of a film set.
Hemingway was one of Key West’s best-known residents; Tennessee Williams and Truman Capote are among the other writers to have been drawn to its tropical climate and bohemian lifestyle. Reviving ourselves in the morning with a caffe con leche from Cuban Coffee Queen (284 Margaret Street), we mosey down to Hemingway’s Spanish colonial villa at 907 Whitehead Street.
Now a museum (US$13; hemingwayhome.com), the rooms have been left as they were when he lived here in the 1930s – even his studio, complete with typewriter, where he wrote his best work. “He had a policy of writing 700 words or until lunch, whichever came first,” says the inimitable MJ Pierce, one of the guides who gives free tours.
In the gardens are more than 50 six- and seven-toed cats, descendants of Hemingway’s first polydactyl feline, Snow White. “Here we have Cary Grant, Duke Ellington and Humphrey Bogart,” MJ says. “But Hemingway gave his funny names such as Dillinger, Friendless and Whorehouse.”
A short walk away, or a long swim from Havana, brings us to the concrete buoy that marks the Southernmost Point. In 2013, after 35 years of trying, endurance swimmer Diana Nyad conquered this section of the Florida Straits in just under 53 hours. With our own long journey to Miami ahead of us, we take a pedal-powered rickshaw back into town, scattering free-roaming chickens along the way. With any luck, there’ll be time to taste a portion of those famous conch fritters before leaving… GETTING THERE- Hertz has 28 rental locations in Miami with prices from US$62 a day in June. hertz.co.uk
- Rates at Sunset Key Cottages, a Luxury Collection Resort, start from US$695. sunsetkeycottages.com
- For more information visit fla-keys.co.uk
