It's been hanging over us for a decade; a rite of passage that every parent has to endure, like the Terrible Twos or combing for nits. One day we would have to take the children to Disney. Not the French one. The real one, in Florida.
Miraculously, though, as our two boys have grown up, it seems we've been granted a reprieve. Neither of them enjoys fairgrounds; in fact they're both positively thrill-phobic. So, we've never made the classic pilgrimage to the Magic Kingdom.
However, craving some sun, and keen to make our first family trip to the US, we've headed for a more laid-back part of the Sunshine State in search of a gentler form of family fun that doesn't require queuing. Apart, that is, from the three hours it takes to get through immigration at Miami.
Instead of heading for the big visitor attractions upstate, or Miami's trendy beaches, we point our rental 4x4 south, towards the Florida Keys, without any clear idea of what we'll find. The Keys are well-known – most people will be familiar with the Ernest Hemingway connection, and possibly recall an image of Humphrey Bogart looking grizzled on a boat. But beyond that, it's all a bit vague.
That's partly because the Keys aren't a homogenous area like the Everglades, but a group of hundreds of small islands, connected by a single road, the Overseas Highway. Stretching some 130 miles across the ocean all the way down to Key West, with long bridges arcing over expanses of open water, the highway follows the same route as the pioneering train track which first connected these scattered islets to the mainland in the early 20th century. It's the only way to drive on to or off the Keys and, crucially, the only escape route if a hurricane strikes.
With that limit on development, the Keys still feel small-scale and old-timey. There are no high-rise resorts, and as you go south, the suburban sprawl of multiplexes and malls thins out, to be replaced by roadside motels, bait shops and the odd ghostly Art Deco garage. The only theme parks are dolphin-based and the nightlife is largely limited to sports bars and mom'n'pop joints selling 57 varieties of Key lime pie.
Most visitors just barrel through the less obvious charms of the Upper and Middle Keys, and push on to the area's most famous – and only proper – town, swinging Key West, a three-hour drive south from Miami. But along the route there are resort hotels and beach restaurants tucked away which offer a taste of breezy, laid-back Keys living, and enough sports fishing and diving to satisfy the most rugged Hemingway disciple.
We whip through Key Largo (less characterful than it sounds) to our first base, the Postcard Inn at Islamorada. The hotel has its own man-made beach, and has recently been given a makeover, leaving it with a salt-scrubbed, retro look, walls of vintage postcards and nautical quotes painted around the place. "Life's an Ocean, Sail It," our bedroom wall shames us. We stubbornly ignore it for the duration.
"Life's a bar, drink it" should be the area's alternative motto. The Postcard Inn is the home of the Keys' original tiki bar – a kind of supersized wooden hut modelled on the dwellings of the islands' indigenous people. It's a no-frills sort of place, which claims to have been the birthplace of the Rumrunner cocktail in the 1970s. Some of the bar-propping locals, as salty as their drinks, look like they may have been here ever since.
From our balcony, we can watch the sun rise over the Atlantic and set over the mangrove-lined Gulf of Mexico. Pelicans divebomb the water, which rarely gets rougher than a gentle swell, the waves broken by the huge coral barrier reef lying a few miles offshore, one of the world's largest. The reef is the area's main attraction – a local tells us that it's the "most dove spot in the US" – and Islamorada's reputation as the big-game fishing capital of the Keys also draws in the visitors. Needless to say, we neither dive nor fish. Instead, it's tempting just to kick back and spend the days stretched out on a lounger, rising occasionally to eat conch fritters at the hotel's beach bar and wonder why Americans ever bother to go to the Caribbean.
A night-time discovery, the Meat Eatery and Tap Room, is a tiny diner knocking out the kind of dude food perved over by London foodies – pulled chicken sandwiches, onion string with beer cheese dipping sauce, mango chipotle ketchup. At home, this place would be populated by skinny kids with tattoos, but here, buzz-cut oldsters in fishing T-shirts sit at the bar nursing micro-brewed craft beers.
This proves to be one of the great mysteries of the holiday – how does the area's relaxed drinking culture flourish when everyone needs to drive home along a two-lane highway of thundering lorries and Winnebagos, moving so fast that just getting on and off it requires an act of courage?
We brave this real-life Scalextric track for a day-trip to the John Pennekamp Coral Reef State Park, up the coast in Key Largo. Here you can experience the Keys in their natural state, kayaking or paddle-boarding up mangrove-lined creeks or snorkelling the reef. We take the landlubber option, and join a group excursion out to the coral reef on a glass-bottomed boat.
Chugging through the mangroves and out to sea, it's all very jolly. Then we drop anchor, and everyone clusters around the viewing windows below deck. Our super-enthusiastic guide points out sergeant-major fish and 3ft-long nurse sharks. The boat rolls and sways. It turns out that looking at fish through the bottom of a pitching boat is like reading in the back of a moving car. One by one, passengers pick their way back up to the rocking deck in search of sick bags, until only the hardiest remain in the hold. A small boy is copiously sick. "Get me off this goddamn boat," the man next to me groans. Over the PA, the undaunted guide breaks into song: "It's all about them sharks, 'bout them sharks, no dolphins!" It's The Raft of the Medusa, but with added pep.
Vowing not to risk another excursion, we head down to the real-life theme park that is Key West. The drive down to the Lower Keys is one of America's great road trips. The highway turns from a test of courage to a thing of beauty, snaking over elegant bridges that occasionally run alongside the skeleton of the old railway track. Azure water stretches away on either side, and mangroves and dense woodland start to replace the straggling roadside development. We're driving to the very tip of the US and it feels like a wild, abandoned place.
Then we hit Key West, the outlaw town at the end of the line. Whatever image you have of the place – the wharfs, tough bars, rum-smugglers and cigar factories of Hemingway's time, or the chic hedonism of its gay-friendly renaissance in the 1970s and 1980s, forget it. The hellraisers and hip settlers have moved on.
It's still a fascinating little town to explore on foot, with its quiet neighbourhoods of elegantly restored colonial houses. But, as Hemingway predicted, the tourists have taken over and it seems to be one long happy hour. The main road, Duval Street, regularly thronged with cruise ship passengers, is strung with tourist tat, Irish sports bars and chain-saloons; like Coyote Ugly, complete with gyrating dancers. As a glimpse of Americans behaving badly, it's fascinating. Normally in the US, you aren't allowed to drink openly on the streets. Here, it's almost illegal not to, and we soon get used to swerving round grizzled oldsters passed out on the curb.
There are plenty of family friendly activities, though, including an excellent aquarium and several museums which peel back the layers of Key West's colourful history. Hemingway's former house, still full of his books and paintings, seems almost untouched, as though he has just popped out to Sloppy Joe's for a drink. Everything is walkable, or a short ride away on one of the dinky tourist trolleys that clank around the island. In fact, with its trolley tours, old-time wooden houses and unrestricted opportunities to invest in Key lime pie, there's more than a touch of Disney World about the place, although Key West's Main Street USA is patrolled by drag queens rather than Mickey and Donald. And little pockets of rackety authenticity can still be found, like the Schooner Wharf, a genuinely ramshackle dirt-floor bar on the harbour. We slide in on high stools among salt-crusted fishermen and sailors, while a terrific bar band of pony-tailed seniors plays Van Morrison classics.
Watching the sun set over the ocean with a frosty margarita in your hand, you can understand why the Keys have offered generations of Americans an escape, not just from cold weather, but from conformity. To use an image the locals would understand, a holiday here is a cocktail, muddling a taste of small-town America with a sweet shot of laid-back Caribbean beach life and a bracing green blast of nature. The Keys may have outgrown their outlaw roots, but they're still quirky, charming and a little bit louche. And certainly a lot more fun than Disney World.
Virgin Holidays (0844 557 3859; virginholidays.co.uk) offers a week in Islamorada from £1,169pp. The price includes flights from Heathrow to Miami and room only at the Cheeca Lodge and Spa, with car hire.
The Florida Keys can be reached from Miami, which is served by American Airlines (020 7660 2300; aa.com), British Airways (0844 493 0787; ba.com) and Virgin Atlantic (0844 209 7310; virgin-atlantic.com) from Heathrow.
Postcard Inn, Islamorada (001 877 781 2690; holidayisle.com).
Tourism Florida Keys and Key West: fla-keys.co.ukReuse content