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The Florida Keys have long been regarded as somewhere rather different, not quite like the rest of America. Not that there’s anything surprising in that; after all, they’re not even part of the mainland. The 100-mile-long string of islands trails like a curve of careless paint drips from the south-east corner of the Sunshine State to within 90 miles of Cuba, and until the early 20th century the only way to get from one end to the other was by boat. Only Key West, the last link in the chain, had anything like a town, its fortune based on selling salvage from ships wrecked on the reef that shadows the Keys. Between there and the mainland were only a few scattered fishermen, renegades, loners and eccentrics.

All that began to change with the coming of the railway – Henry Flagler’s great engineering triumph, damaged beyond repair by the 1935 hurricane – and, three years later, a road with 43 bridges to tether 42 of the islands together. These days, you can hurtle – if that’s the right word with a strict 55 mph speed limit – to the heart of Key West in about four hours. With just the one highway, it’s the easiest road trip around, with regular mile markers so you know exactly where you are.

It would be perfect for cruising in a slick Fifties convertible if it weren’t for the weather, which is either hot and very sunny or hot and rainy. But despite Highway 1 (also called the Overseas Highway), the Florida Keys still feels like a place apart, a laid-back final frontier where anything goes and everyone is welcome – especially if they’re buying the drinks.

There is sophistication here, too, but it’s one based on simplicity rather than glitz; you can wander round in your most battered shorts and no one will turn their nose up at you. Yes, there are fast-food outlets beside the road, particularly in the Upper Keys, but they’re outnumbered by family-run restaurants where the emphasis is on fresh, wholesome ingredients and charming service.

Take The Fish House on Key Largo, for instance, which has been serving up local seafood for nearly 20 years. From the outside it’s nothing remarkable, but the food is superb, whether it’s perfectly grilled lobster or yellowtail snapper pan sauteed with lemon and sherry. Even the decor is memorable: an endearingly kitsch mishmash of appropriately maritime items, including nets pinned to the ceiling and threaded through with multicoloured fairy lights in the shape of fish, starfish and shells.

Perhaps a little disconcertingly, Key Largo is also the place to see your next meal in its natural environment, a fact you’ll be alerted to by the plethora of dive shops and places selling snorkelling gear and glass-bottomed-boat tours. The John Pennekamp Coral Reef State Park is, along with Looe Key further south, one of the best preserved parts of the reef that stretches well beyond Key West.

Here, much of the coral is still alive, preserving a fragile ecosystem that supports anything from tiny shrimps to fearsomely toothy barracudas and sleepy (non-man-eating) nurse sharks. Against the rich blue background of the water, there is colour everywhere. Ethereal jellyfish are lit from within by neon-pink filaments; parrotfish – their bodies a mix of blue, yellow, pink and green – mingle with wasp-striped angelfish; the reef itself looks like a well-used palette. If you aren’t a certified diver, get in the water and snorkel – or even learn how to dive.

If it’s above-water adventure you’re after, though, you’re better off heading further south to Islamorada, otherwise known as “fishing capital of the Keys”. It’s a sobriquet that conjures up visions of rich but not-very-fit middle-aged men hauling on very large fishing rods and imagining they’re Ernest Hemingway, the ultimate he-man and former Keys resident – as you’re not allowed to forget. Never mind the vision; the reality, as you head out at peachy dawn towards the Gulf Stream, is that it’s the original adrenalin sport. Nothing beats the thrill of landing a mahi-mahi for your lunch, or a 35-pound amberjack that leaves your arm muscles aching for days. If the experience has you – forgive the pun – hooked, the tackle shop next to the Islamorada Fish Company restaurant is mind-bogglingly huge and worth a browse. But you may have to leave it until after your catch has been cooked up for you (try it fried in coconut batter), as you’ll find all that sea air gives you a hearty appetite.

As you head south, the tempo slows a little more. There’s a feeling of laziness in the air, of days filled with messing around in boats or a touch of gentle fishing, with a beer or two at sunset in some waterside bar. Away from the main road, you begin to find more in the way of rustic-looking cafés packed with savvy locals; for more than 50 years the scrubbed-wood Seven Mile Grill has done a steady trade in conch chowder and plump shrimps steamed in beer. Attractions are just as low-key: a few small and eminently missable museums; a 64-acre plot of virgin subtropical forest at Crane Point Hammock; the Dolphin Research Center at Grassy Key.

The most impressive sight is Henry Flagler’s Seven Mile Bridge, built between 1908 and 1912 to carry the new railway. Though the bridge is no longer used, it’s a technical marvel – although not marvellous enough to withstand the 1935 hurricane unscathed. For the less technically minded, the most impressive thing about Flagler’s bridge and its 1982 road-carrying replacement is the view as you cross. It’s almost like flying; the car seems to glide above the water. As you look down, it’s hard to believe anything could be that colour, a luminous mix of turquoise and jade. No wonder the fishermen on the old bridge seem so languid in their movements; they’ve been mesmerised by the scenery.

Time grinds almost to a complete stop at Bahia Honda State Recreation Area, in the Lower Keys. This blissfully uncrowded park, where visitor numbers are deliberately restricted, is worth the small entry fee a hundred times over for its beaches alone. There are two – one on either side of the island – and they are widely considered among the best in America. It’s not hard to work out why when you see the twin crescents of soft, white, powdery sand lapped by an emerald sea. Bobbing in the warm water, which seems to stay waist-deep for miles, it’s impossible to be anything other than deeply, smilingly relaxed and refreshed. Which is just as well, because the next stop is Key West, self-styled party capital of the Keys.

What can you say about a place where even the sunset, that not-exactly-unexpected daily event, is an excuse for a celebration? Every evening, crowds of locals and visitors alike gather in Mallory Square to have a drink or two and watch the sun go down. While they wait, an eccentric collection of street entertainers provides a welcome sideshow. It’s not often you get to see a cat tamer, after all, though it’s more fun seeing the rebellious felines refusing to go through their paces.

That’s the trouble with Conch cats; they always want their independence. So do the Keys inhabitants, who in April 1982 famously seceded from the Union and declared Key West the capital of a new Conch Republic in protest over US Border Patrol searches on every car travelling between the Keys and the mainland. It did the trick. The searches, and the revolt, were soon abandoned, but you can still buy a Conch Republic passport.

There’s more to Key West than carousing and rabble-raising, though. For a start, it’s one of the few places in the US where you can get a decent cup of coffee, thanks to the presence of Cuban settlers (the island is just 90 miles away). One thimble-sized cafecito – small, black and sweet – can restore your soul in seconds and keep you going for hours.

History and literature fans finally get their reward here, too; they can spend hours wandering back streets lined with glorious old buildings, anything from ornate “gingerbread” houses to tiny wooden cottages with wraparound porches. One house you can’t miss is the one that Hemingway lived in for 10 years, now open to the public. It’s a pretty enough building made special by its literary association, its laconic guides and the resident cats with their freakish six- or seven-toed feet.

Other places, too, have their Hemingway connections. At Blue Heaven Café close to where he lived, the writer used to referee Friday-night boxing matches in the Thirties. Now it’s an unusual and popular lunch spot, where everyone eats in the yard with chickens pecking round their feet; the delicious Bahamas-style home cooking is worth stopping for. Then there are the two Sloppy Joe’s bars where he drank: the original on Greene Street, where Captain Tony’s is today; and the place to which its contents were transported overnight in 1937, followed by all the regulars, apparently in protest over a rent hike.

But if you think Hemingway would recognise his old home if he saw it today, think again. The tolerant attitude of its natives may be the same – hence a thriving gay community, for instance – but the place itself has been thoroughly tarted up in the past two decades. The town’s main thoroughfare Duval Street, once borderline sleazy, is now rather smart and other quarters have been similarly refurbished.

Though some people feel Key West is in danger of losing some of its louche charm, it has also meant that visitors have a far wider and classier choice of guesthouses and B&Bs, many in restored historic houses and some with that rare Key West commodity, their own parking spaces. That’s something to look out for when you’re choosing accommodation. People might drive to and from Key West but, unless they absolutely have to, they don’t drive once they’re there, and it’s good to have somewhere safe to leave your wheels.

Of course, if you’re not driving you can drink, and plenty of visitors do, paying their own peculiar homage to the past by getting pie-eyed in every bar that Hemingway ever visited. You might expect this would mean late-night impromptu boxing matches, but the relaxing air of the Keys makes for happy drunks who are more likely to tell you what great feet you have, ma’am, from their pavement-level vantage point.

Mostly, though, a typical evening means sunset drinks, dinner at one of Key West’s many restaurants and live music at a bar. If it’s clubbing you want, you’ve come to the wrong place. Isn’t that rather strange in such a party-loving place? Maybe – but they like to do things a little differently here.

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