Photo: Jametlene Reskp / Unsplash


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It was February 1983 when I jumped into a rickety old station wagon with three unsavory student buddies and drove 35 hours from Ontario, Canada, to Florida on a Spring Break race for the sun. We purposely avoided the partying crowds inDaytona Beach and Miami by driving as far south as the road would take us.

We only stopped when the highway ended at Mile Zero. Here, we found ourselves in laid-back, free-spirited, artistic, quirky, and scenic Key West, a place closer to Cuba than to Miami; closer, as the locals proudly point out, 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. Now, almost 40 years later, I have finally returned to relive that Key West drive, taking the time to enjoy just some of the many fun things to do in the Florida Keys.


An Epic Florida Keys Road Trip… in Reverse


First Stop: Key West for Sunsets and Sightseeing
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Key West features a unique and laidback US-Caribbean  charm (Photo: Diego V. Simoes / Shutterstock)

I step off a plane and onto the tarmac at Key West 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 only a vague memory of having done before. Although, this time, I am approaching the trip in a much more mature and civilized manner.

I crane my head out the van window, seeing familiar sites in this coolest, funkiest, most eclectic, and offbeat little city in America. Tourists in floral shirts, baggy shorts and Panama hats stride up and down the quaint, palm-shaded streets, while locals dressed in whatever strikes their fancy, including a fellow in a Spiderman costume, seem somehow both fitting and incongruous when set against the town’s 19th century architectural charm.


Great Key West Food and Rockin’ Nightlife
02. Sloppy Joes Bar
Sloppy Joe’s Bar on Duval Street was a favorite Key West local for Ernest Hemingway (Photo: James Ross / LuxuryUnitedStates)

From the unique locals and vibrant turquoise waters to the exciting history and home-grown cuisine, every element of Key West is colorful. 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.

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.


Key West Butterfly Conservatory on a Florida Keys Road Trip
The Key West Butterfly Conservatory is a must-visit for nature lovers (Photo: Bryan Dearsley / LuxuryUnitedStates)


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 pilgrim 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, I soak in the history and shipwreck archaeology at the Mel Fisher Maritime Museum, nature at the Butterfly & Nature Conservatory, and the Key West Aquarium and then I get out on the water on a diving tour.


Forty-Two Bridges North
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A Florida Keys road trip crosses 42 bridges and offers dramatic views of historic rail bridges (Photo: Micky Ritzsche / Unsplash)

The many worthwhile Florida Keys 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 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.

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, and 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 the classic Americana roadside, kitschy shops, offbeat attractions, and funky restaurants. 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.


Paddling at Lone Pine Key
4. Eco-Kayak with Bill and Scupper
Eco-Kayak’s Bill and Scupper lead kayaking adventures at Lone Pine Key (Photo: James Ross / LuxuryUnitedStates)

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.


The Turtle Hospital at Marathon
5. Turtle Hospital turtle swimming on a Florida Keys Road Trip
A stop at the Turtle Hospital in Marathon is a must-do (Photo: James Ross / LuxuryUnitedStates)

Marathon is a renowned boating and family destination, and home to the 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.

I meet with the facility celebrity, Bubble-Butt, the unfortunate victim of a boat collision. 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.


The African Queen and John Pennekamp Coral Reef State Park
John Pennekamp Coral Reef State Park sign with car
John Pennekamp Coral Reef State Park is a must-stop for Florida Keys roadtrippers (Photo: Bryan Dearsley / LuxuryUnitedStates)

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 famous African Queen, the same steam from the renowned movie of the same name. Like Bogart at the tiller, I guide the small ship on a tour of the inner harbour.


Delicious Seafood and Key Lime Pie
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No trip to the Keys is complete without a slice or two of key lime pie(Photo: Takuya Nagaoka / Unsplash)

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 debate about the world of politics here, but what is hotly contested is whether the key lime pie should be topped with whipped cream or meringue. I find both delectable in my extensive research, even the strange chocolate-covered key lime pie on a stick.

If you were born in the Keys you are called a “Conch.” Being labelled 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 almost 40 years to return to such a charming destination – well, you can call me a “Conch Fritter.”

The Florida Keys 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.


If You Go: LuxuryUnitedStates Recommends


Planning a Florida Keys road trip? For more information on this beautiful and unique part of Florida USA, be sure to visit and

 Looking for somewhere great to stay while you explore the Keys? The following Florida Keys resorts come highly recommended for their high-quality accommodations:

For more great ideas of great places to stay in Key West, click here.




Contributor James Ross is a travel writer and columnist, and author of the books Cottage Daze and Still in a Daze at the Cottage. He lives in Muskoka, Ontario, Canada.


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