As great drives go, taking US Highway 1 from Miami to Key West is pretty undemanding. Slide into your car, push the gearstick to "drive" and sit back for the next three hours and 260 kilometres, skimming over Seven Mile bridge - along with 41 others. Of course, chasing Florida's tail is more fun than it sounds. Especially when you're in a convertible, with the sun shining, hair backcombed by the breeze and a stream of Latin sounds rumba-ing from the radio. (By the end of the road, you'll be closer to Havana than to Miami.) The trouble is that the southernmost city in the US makes a limp sort of climax to the journey.
Key West is far more picturesque than its seedy reputation promises, with a neat grid of gingerbread houses wilting in the tropical heat. Yet the maverick spirit that once drew Ernest Hemingway, Tennessee Williams, poet Elizabeth Bishop and other artists and eccentrics to town has now been replaced by something as classy as Falikraki in high season. "Margaritaville" bars? Check. Pirate museums? Ah-har. "I love cocks" bumper stickers? You bet (apparently a reference to the city's famously large population of roaming chickens rather than its gay scene). Even the Hemingway museum, in the writer's glamorous former home, is disappointingly twee, with a tour that makes more of the resident six-toed cats than any of Papa's writings. In short, the overall effect is as tacky as a slice of Key lime pie.
So why come here? Because away from the happy hours and the spangly hot pants, the 45 islands that make up the Keys are slowly starting to regain their 1950s glamour. The trick is not to race down to Key West, but to take a deep breath, slip the roof down and enjoy the ride, pootling slowly south-west via a discreet string of insider haunts.
First stop should be the island of Islamorada. With its local restaurants and low-key resorts, this traditional sport-fishing hangout feels like a functioning village rather than a roadside pit-stop. Roughly halfway between Key Largo and Key West, it also has enough chi-chi hotels to sustain regular waves of weekending Americans looking for sophisticated sun-worshipping within Havaiana-lobbing distance of Miami.
Take the 16-suite Casa Morada, a former motel bought in 2002 by a trio of former Ian Schrager employees and reopened soon after, having been nipped and tucked to the tune of $1m. Then there's the Moorings. Currently plastered across the cover of Taschen's glossy Great Escapes North America hotel book, the resort's 18 pretty cottages, scattered throughout a former coconut plantation, look as if they've hopped on a flight from New England. With their white picket fences, Ralph Lauren sheets, lush tropical gardens and direct access to one of the softest sand beaches in the area, it's no wonder that fashion shoots make up a sizeable chunk of the resort's business.
The real attraction of the Moorings, though, is the landscaping. More vintage crop than cutting edge, the property was originally built in 1936 as a private estate and has the kind of organic layout that comes from years of gradual development, something that appealed to its French owner, Hubert Baudoin, when he bought the site in 1988. At the time, it came with planning permission for 250 holiday units - each with an ocean view.
Fortunately, Baudoin's vision stretched beyond the dollar sign. "The plan came with the land and it would have been a very lucrative venture, but no matter how much money you have in the bank, you still have to look at yourself in the mirror. I could not live with that," he said. Eighteen years on, Baudoin has stuck to his word. Now, almost all the cottages are of a different design and shape. They are also deliberately set back from the beach, both to give people privacy on the sand and to make the place feel less like a resort. The cottage interiors, too, are equally well thought out, stylish enough to satisfy the likes of demanding New Yorkers but also deeply homely. Nothing feels too interior-designed shiny and most also have kitchens, an asset I was surprisingly grateful for after a few days of mountainous American restaurant portions.
Not that you have to do your own cooking. The Moorings also owns two restaurants, less than 10 minutes' walk away on the other side of the island; the Morada Bay Beach Café, with a sundae-like swirl of ice-cream-coloured tables set overlooking the water, and Pierre's, a formal restaurant and bar in a chic plantation-style house.
After a couple of days lapping up and down the pool and sinking sunset mojitos at Pierre's, I could have booked in until Christmas. But it would have been a shame not to make it further south than Islamorada, because there are other attractions along the road - such as the laid-back Key Fisheries café, where you can get fresh-from-the-water crabcakes, shrimp and, if you like your food snappy, gator sausage sandwiches. Or visit the turtle hospital on Marathon. Set up in 1986, on the site of a former topless dance bar, it now shimmies in 50 to 80 sick or injured animals - by turtle ambulance - to treat and rehabilitate each year.
Take a tour around the centre's recuperation tanks and it soon becomes clear just how much a turtle takes his life into his flippers swimming off the Keys. If you're not hit by a boat, attacked by a shark or tangled up in netting, there's always the chance you might develop cancer. Then, if you make a good recovery, you're released back into the terrors of the water. Those too sick to leave stay on, like current long-term resident Joey, a little green turtle with neurological problems who swims in circles, or flips up and floats on his back.
Back on the road, about 50km before you reach Key West, is the flashiest place in the Keys, Little Palm Island. This luxury five-acre island is home to 28 sybaritic bungalow suites, just off shore from Little Torch Key. (Guests are shuttled across in a gorgeous, wood-lined launch.) Its two claims to fame are both presidential - Harry and Bess Truman were regulars here when Key West played host to the winter White House and, in 1962, the island stood in as the South Pacific for the filming of PT-109, a dramatisation of JFK's wartime experiences. In a nice show of political muscle, when JFK came to watch the filming, his father, Joe Kennedy, insisted that the state installed electricity and mains water for the event.
Today, besides slightly more modern facilities - there's an elaborate spa - and the building of those 28 suites, not a lot has changed. Little Palm Island is an old-school kind of place, booked out by couples wanting somewhere to clink champagne glasses on an anniversary or pop the question over a beachside dinner. If you're allergic to rose petals being scattered on your bed or having to ring something called "the Quarterdeck" rather than reception, this isn't for you. But if you can put up with a little cheese, there are good reasons for coming here.
One is the sheer mind-boggling service - when you leave the island, not only will someone bring round your car and put your bags in the boot ready to go, but they will also have turned on the air-conditioning and popped fresh bottles of water in the car drinks holder. The other big draw is the access to nature. Step out of your suite and you can't go more than a hundred metres without spotting a cute, bambi-like Key deer. The smallest race of North American deer, native to the lower Keys, there are thought to be less than 1,000 of these endangered wild animals left. They share the island's mangroves with huge green and black-striped iguanas, spoonbills, herons, willets and blink-and-you-miss-them red-winged blackbirds.
The highlight of the trip came as I sat on an otherwise-empty sun deck that ran elegantly around the back of the island, looking out over sparklingly clear water. First came the flap of a collection of enormous wings, then a flock of pelicans crossed the water right in front of me, so low that they were almost skimming the sea. The next moment they swooped hungrily down. I just hope they hadn't spotted a little green turtle swimming in circles.
The writer flew from Heathrow to Miami with Virgin Atlantic (08705 747747; www.virgin-atlantic.com). British Airways (0870 850 9850; www.ba.com) and American Airlines (08457 789789; www.american airlines.co.uk) also fly the same route.
To reduce the impact on the environment, you can buy an "offset" from Climate Care ( www.climatecare.org; 01865 207 000).
The writer hired a Chrysler Sebring convertible through Dollar Rent a Car (0808 234 7524; www.dollar.co.uk). Rental starts at £131 per week, or from £198 for a convertible.
The Moorings, Islamorada (00 1 305 664 4708; www.themooringsvillage.com). Self-catering cottages start at $491 (£273) for two nights. Little Palm Island Resort (00 1 305 872 2524; www.littlepalmisland.com). Bungalows start at $778 (£432). Casa Morada, 136 Islamorada (00 1 305 664 0044; www.casamorada.com). Suites from $331 (£184).
The turtle hospital (00 1 305 743 2552; www.turtlehospital.org).
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