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By Jamie Ross
(for Travel Writers’ Tales)

I step off a plane and onto the tarmac at Key West’s International Airport, and then out of the humid heat and into an air-conditioned van. My mission – a Florida Keys road trip, a drive northward up the coral cay archipelago that arcs gently down in a south-southwest direction from mainland Florida. It is a journey that I have a vague memory of doing once before, although this time I’m approaching the whole thing in a different direction, and in a much more mature and civilized manor.

Photo 1 The Mile 0 marker

It was 1983 when I jumped into a rickety old station wagon with three unsavory student buddies, and drove 35 hours from Ontario to Florida in a Spring Break race for the sun. We purposely avoided the partying crowds by continuing on as far south as the road would take us, the final stop on the Overseas Highway, and found ourselves here, in laid back, free-spirited, artistic, quirky, and scenic Key West, a place closer to Cuba than to Miami, closer, in fact, to its Cuban neighbours than to a Walmart. As young students escaping a Canadian winter, we delighted in Key West’s tropical climate and seemingly continuous happy hour.

I crane my head out the window, seeing familiar sites in this the coolest, funkiest, most eclectic and offbeat little city in America; tourists in floral shirts, baggy shorts and panama hats, locals dressed in whatever strikes their fancy, including a fellow in a Spiderman costume, all striding up and down the quaint, palm-shaded streets amongst the town’s 19th century charm.

From the unique locals and vibrant turquoise waters to the exciting history and home-grown cuisine, every element of Key West is colourful. I arrive at my downtown hotel just in time to watch an iridescent sun melt into the blue sea. While artisans peddle unique handicrafts on the docks of historic Mallory Square, jugglers, acrobats, fire-eaters, stilt walkers and performing cats draw applause from sunset revelers celebrating a daily ritual that never seems to disappoint.

Photo 2 Sloppy Joes Bar

The nightlife is a spectacle not to be missed, a mixture of cultures, rhythms and lifestyles. As it was those many years ago, Duval Street is the hub, a bit wild, but that’s part of the charm. I grab a stool at Sloppy Joes and raise a glass to Ernest Hemingway, once a regular patron. In the daylight, I hop aboard the Old Town Trolley for a delightful guided tour of the town, jumping off in the old Bahamian neighborhood to continue my literary pilgrimage at Hemingway’s two-story home. His studio, where literary miracles were spun, is exactly as he left it, and about fifty ‘Hemingway cats’ roam throughout the lush grounds. Afterwards, soak in the history shipwreck archaeology at the Mel Fisher Maritime Museum, nature at the Butterfly & Nature Conservatory and the Key West Aquarium and get out on the water with a jet-ski or on a boat or diving tour.

The worthwhile attractions are many, time is the one thing I don’t have enough of, and so after two days of fun in Key West, it is time to set off up the road. Drivers can travel the full 181 kilometre (113 mile) length of the Overseas Highway between Key West and the Florida mainland in four hours, but to fully experience the flavour of the Keys’ five regions, stretch that road-trip to four days.

Photo 3 The Seven Mile Bridge

The islands lie along the Florida Straits, dividing the Atlantic Ocean to the east from the Gulf of Mexico to the northwest. The highway is an engineering marvel, you’ll cross 42 bridges on route, some stretching over impossible stretches of water. The scenery is delightful, from the tidal flats and aqua-blue water dotted with tropical islands, to classic Americana roadside; kitschy shops, offbeat attractions and funky restaurants.

Photo 4 Eco Kayak Adventure with Bill Keogh and Scupper

I remember sun-tanning on the nicest beach in the Keys, at Bahia Honda State Park just north of Key West – but there will be no sunbathing on this trip. At Lone Pine Key, I enjoy a kayaking eco-adventure with Bill Keogh and his dog Scupper. We paddle across the choppy straight and into the twisted roots of the mangrove swamp, on the lookout for dolphins, sharks, rays or crook-jawed crocodiles. What I see are osprey resting on channel buoys, crabs scurrying over stone outcrops and the miniature Key deer, a tiny species of whitetail, foraging along the grassy shoreline. It is a delightful way to explore, and I make a note to return to tackle the much more ambitious Key Largo to Key West overseas paddling trail.

Photo 5 Smelly Cat at the Turtle Hospital

Marathon is a renowned boating and family destination, and home to a Turtle Hospital at MM 48.5, one of the few state-licensed veterinary centers in the world dedicated solely to the care of sea turtles. The hospital treats injured sea turtles and, whenever possible, returns them to the wild. Known as the Sport-Fishing Capital of the World, Islamorada is heralded for its angling diversity. You’ll also find the second oldest marine mammal facility in the world here, Theater of the Sea, at MM 84.5.

At Key Largo, the longest island of the chain be sure to visit John Pennekamp Coral Reef State Park, incorporated within the Florida Keys National Marine Sanctuary. These protected areas feature more than 50 varieties of delicate corals and more than 600 species of fish. Key Largo is also the home of the African Queen, the same steam from the famous movie of the same name. Like Bogart at the tiller, I guide the small ship on a tour of the inner harbour.

Photo 6 The African Queen

Island cuisine offers fresh seafood (Stone crab claws, spiny lobster, and yellowtail snapper), Caribbean flavors, and Key West charm. A slice of Key lime pie, the Keys’ signature dessert, is a heavenly end to any meal. There isn’t much debated about the world of politics here, but what is hotly contested is whether the region’s well-known and prized desert, the signature key lime pie, should be topped with whipped cream or meringue. I find both delectable in my research, even the strange chocolate-covered key lime pie on a stick.

If you were born in the Keys you’re called a “Conch.” A “Fresh-Water Conch” means you’ve lived here for seven years, and an “Honorary Conch” is someone who does something special for the region. I suppose if it takes you 34 years to return to such a charming destination – well, you can call me a “Conch Fritter.” It had grown up some since my last visit, sure, but the friendly feel and laid-back simplicity of the place hasn’t changed at all - the same charming details that rise above the fog of that long-ago visit remain; key lime pie, ocean fishing, diving the reefs, buskers on the wharf, Sloppy Joes, sunsets and Hemingway.



For Information: and

Accommodations: The Margaritaville Key West Resort

The Amara Cay Resort

PHOTOS by Jamie Ross

1. The Mile 0 marker
2. Sloppy Joes Bar
3. The Seven Mile Bridge
4. Eco Kayak Adventure with Bill Keogh and Scupper
5. Smelly Cat at the Turtle Hospital
6. The African Queen

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