Everyone loves the idea of a classic drive – a hazy dream of open roads, spectacular scenery and perfect playlists. But when does reality match the fantasy?

From the Pacific Coast Highway to the Amalfi Coast, the world’s great drives have become traffic-clogged, overexploited victims of their own success. The greatness of a road diminishes with fame. So forget these hackneyed tourist trails and try our new classics, including one drive that's exclusively online, Miami to Key West.

Packages, unless otherwise stated, are per person, for seven nights, including accommodation and return flights from London

AMERICA

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The brochure image is of cigars, Castro and Havana. Find a whole new Cuba by hiring a car and heading off

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THE CLASSIC

The Overseas Highway — Miami to Key West

On paper, it's a winner: 126 miles of blacktop that flees downtown Miami like a rum-running fugitive, leap-frogging the Gulf of Mexico across 32 islands from Key Largo all the way to Key West. It should be a blast, but sadly the Overseas Highway isn't a road trip. It's a bridge trip, and driving it means joining a slow-moving convoy of Winnebagos, watched by cold-hearted cops who are meaner than a half-starved 'gator. And to what end does one endure this watery highway? Key West is a cynical, overcommercialised atrocity where you'll probably end up staying the night because you can't face the four-hour drive back to Miami.

THE ALTERNATIVE

The Tamiami Trail

Distance: 275 miles Time required: Two days

Route 41 is Florida's real highway. From Tampa to Miami, it plunges through the dark heart of the sunshine state. First stop as you head south is Gibsonton, a retirement community for sideshow freaks established in the 1940s by 8ft 4in Al Tomiani and his wife, Jeanie, 2ft 6in. If you're in the town's Showtown Bar and Grill (10902 Highway 41 South) and you spot a tattooed dwarf and a bearded lady duetting I Will Survive, don't blame the booze.

Continue south along the Redneck Riviera to Fort Myers Beach — where they make the crazy golf crazier by adding live alligators — and Naples, where the trail swings east. You'll see more 'gators here, stroppy monsters who bask on the roadside, glaring at the few passing cars. "Men, money and machinery," cried the entrepreneurs who commissioned the road in the 1920s. "Much misery and moccasins," countered the workers who dug and dynamited their way across this snake-infested wilderness.

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