The southern Florida road trip between Naples and Key West will give us a good look at the Gulf Coast and the Everglades along with a chance to drive the 250-kilometre stretch of Highway 1 between the two places.

I know the Keys highway can be a slow drive, so I thought a road game might be in order. Nothing like a challenge or game to fill time getting down the highway. Standards like road-sign bingo, keeping score of car makes or counting the number of different animals might seem silly, but they do have a time and place on the road.

“I’ve decided to find 10 favourite Cars of the Keys ... Keys Cars,” I say. My wife Lisa pays a cursory glance.

“I’ll find 10 candidates then force myself to choose an overall favourite.” This is going to drive Lisa nuts. She claims I make a game out of everything.


“1962 IMPERIAL!” I scare the daylights out of her barely three blocks from our hotel in Naples.

Chrysler’s premium luxo-wagon has always been a favourite. With its spacey pod headlights and gun-sight taillights sitting atop a fine set of tail fins, folks in my hometown thought people who drove Imperials were captains of industry.

Two blocks later, I wheel our rental car into a service station and park beside a powder-blue 1967 Lincoln Continental convertible. Jackpot.

“It has a 462-cubic-inch engine. That’s 7.6 litres, baby. They didn’t bring out the 460 V-8 until 1968. That one doesn’t have side marker lights, so it has to be a ’67.”

Lisa says I have a glazed-over clothes-shopping look.

Driving south out of Naples on Highway 41, I rationalize the Continental and the Imperial will count even though they surfaced before we reached the Keys.

The road veers east into the Florida Everglades. No roadside relics for my list but Panther Crossing signs, alligators lurking in the ditches and the Skunk-Ape Research Headquarters keep us entertained.

Eventually we turn south and pick up US Hwy 1 toward Key West, which is the most southern town in the United States.

The drive through the Keys is not a fast one. I’ve driven it a few times and always think it’s the longest 250 kilometres on the planet.

No matter. Where else can you drive for hours across a series of islands trickling off the bottom of a country?

The road is heavily patrolled by radar-toting police so I putter along taking in the scenery keeping an eye open for more relics. “1965 Econoline pick-up!” I yell, pulling off the highway. “I always wanted one of these.”

The first-generation Ford Econoline with the engine between and behind the front seats was a big seller when they hit the market in 1961.

We finally arrive in Key West and I check out a ratty-looking ’64 Chevy Nova and a dilapidated VW convertible loaded with wharfing materials.

Key West is bustling with tourists. The ones who are not strolling the Duval Street strip or loitering in boozy Ernest Hemingway hangouts are buzzing about on scooters or silently sliding around in rented electric open-air buggies. Of course we rent one and comb the back streets looking for my quintessential Florida car.

A full-sized Dodge van gets my attention. It’s big and bold in its flowery hand-painted livery and plywood minarets protruding from each side.

Then I spot it. I don’t know if it’s the corrugated steel roof or the marine themed paint job that has me about to declare a winner in my Keys game.

Or was it the sign painted across the back of the mid-1980s Lincoln Continental.

“Land Yacht.”

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