Touring the Florida Keys

“That there’s one purrrdy bike, son.” My eyes widened and the hair on my neck stood up on end as I turned around in fear of finding myself in a real-life Deliverance scenario. Thankfully the stranger meant no harm and was legitimately complimenting the 2014 Harley-Davidson Street Glide Special I was riding from Miami to Key West. I stopped unpacking the saddlebags and stood up to address his inquiries about the bike. He told me how he and his buddies also staying at the Bayside Inn in Key Largo were spending the winter riding around the southern States. I told him I’d just landed that morning from Canada to escape the winter weather myself. “Canada? Heard it’s nice up there, but ain’t never been,” he responded in a deep, slow drawl as he gently patted the pistol holstered on his belt, “Y’all don’t let us bring our guns, so we ain’t comin’.” We continued to exchange pleasantries and he invited me to join them for a beer later before adding, “Y’all better lock that bike up good and tight tonight otherwise she may not be there in the mornin’.” He gave me a wink and a smile as he went on his way. Outfitted in distinctively striking Sand Cammo Denim paint, the Hog got a lot of attention throughout the week, but that interaction was among the most memorable.

The Street Glide Special’s Sand Cammo Denim paint got a lot of attention, even if Dustin didn’t want it.

It was winter and I’d been hibernating over the previous months, which allowed me to catch up on some classic books I’d been meaning to read. I found myself drawn to the works of literary giant Ernest Hemingway and was eager to find out more about his adventurous and ultimately tragic life beyond the pages of his legendary work. I discovered that he spent the better part of a decade in Key West and wrote some of his most celebrated novels there, including For Whom the Bell Tolls which I happened to be reading. It seemed like an intriguing destination worthy of exploration. That, and it wouldn’t be snowing there. I could have rented an RV or a convertible like seemingly every other tourist on the road did, but I decided the Florida Keys in February would be best experienced from the seat of a motorcycle.

‘Project Rushmore’ addressed outdated elements and idiosyncrasies faithful HD owners had been lamenting for years.

Among the first models to be launched as part of Project Rushmore, this Street Glide was designed to address outdated elements and idiosyncrasies the faithful owners had been lamenting for years. Improved aerodynamics, ergonomics and an integrated GPS, were among the advancements. They paid off. It rides smoother, handles better and brakes faster.

Stress is a four-letter word in the Keys and it doesn’t take long to become acclimatized to the slower pace of life there. You can’t help but let your shoulders relax. Grinning from ear to ear with the sunshine on my pale face, I set my course to Key Largo. As the sun dipped lower in the sky, the scent of saltwater air floated on the warm breeze as I passed through the Glades National Park. Heeding the many warning signs along the side of the road, I kept a keen eye out for crocodiles.

Dustin kept the motor running while snapping this shot…just in case.

Settled into my room at the Bayside Inn after my interaction in the parking lot, I swapped my jeans and boots for shorts and sandals. Each and every evening, locals and tourists alike are invited by the sound of a conch shell horn to congregate on patios and beaches to enjoy the sunset – a Florida Keys ritual. Whatever work you may happen to be doing, it stops at sunset. Unless you’re Derek, the bartender at Snook’s Bayside Restaurant. Sidling up to the tiki bar to have dinner and a couple cold beers while enjoying enjoy some live music, we became fast friends. A classic bartender who seamlessly mixed cocktails and delivered food, he simultaneously introduced patrons to each other by name and hometown while regaling everyone with entertaining stories at the same time. He even remembered my name and drink choice, cracking me an ice cold Yuengling before I could even sit down when I returned later in the week. If you happen to find yourself in that part of the world, tell him Dustin from Toronto sent you.

I awoke from a deep, restful sleep the next morning, greeted by blue sky and the sound of the ocean lapping at the sandy beach outside my window. It was a magical feeling to realize that the only thing I had on my itinerary for that particular day was to explore the Florida Keys in the sunshine. Logging in to Facebook while I waited for my morning coffee to percolate, my feed was littered with friends and family lamenting the frosty temperatures and accumulating snow back home. It was then that I decided to go off the grid, shut off my phone and truly enjoy my time away.

Strapping on my helmet and sliding on my Wayfarers, I settled into the saddle and felt the familiar 103 C.I. V-Twin gurgle then roar to life beneath me. I noticed that none of the other riders who were setting off for the day were wearing a helmet. I decided to strap mine to the side of the bike and set off. The sun on my face, the wind in my hair (back when I had hair), the Allman Brothers Band playing through the speakers – life was good. I then recalled that guitarist Duane Allman was killed in a collision while riding his Harley-Davidson. Regardless of whether he was wearing a helmet at the time (legend has it, he’d cut the chin strap off), paranoia crept in and I began to calculate all the various risks on the busy road more critically. I pulled over and put my helmet back on.

The Florida Keys are a beautiful place, but much busier and developed than expected.

I became increasingly disappointed to find that the natural beauty and vibrant culture of the Caribbean during Hemingway’s time had been replaced with the epitome of modern Americana. Connoisseurs of fast food restaurants or tacky souvenir shops will rejoice, but I’ll admit I was hoping it would feel more remote and less suburban. US Highway 1 connects the Keys through a series of bridges of varying size, including the massive Seven Mile Bridge that joins Knight’s Key in the Middle Keys to Little Duck Key in the Lower Keys. It is a strange sensation to cross a seemingly endless bridge surrounded by turquoise water. Remnants of the old railway bridge can be seen in many places along the route providing a glimpse into the history of the region. Completion of the Oversea Railway from mainland Florida was commemorated with the first train arriving in Key West on Jan. 22, 1912, changing the Keys from an isolated outpost reachable only by boat to an accessible destination for tourists and cargo. The railway was the brainchild of Standard Oil tycoon Henry Flagler, who barely lived long enough to see his vision and investment come to fruition.

The Keys are connected by a series of bridges linking US Highway 1 to the continent.

As I rode through Marathon Key, I saw a bright yellow and orange biplane and decided it would make for a good photo with the bike. The pilot happened to be prepping the airplane for an upcoming flight, so I parked on the edge of a service road and approached him to see how much it would cost to get a tour of the Keys from the sky. The driver of a grey Ford Explorer interrupted us as he pulled up. As I recall, the conversation went something like this:

“Is that your bike?”
“Yes it is.”
“What are you doing?”
“We’re just talking.”
“You shouldn’t park here.”
“Okay, thank you for the tip.”
“Why are you parked here?”
“We’re just chatting.”
“I think you should park somewhere else.”

I looked around, confused, as there were no other people or vehicles in the vicinity of the tiny airfield. I couldn’t fathom why this stranger was so annoyed. The conversation continued and escalated from there as this surly gentleman continued to interrupt my conversation with the friendly pilot who seemed equally bewildered.

“I think you should move the bike,” he insisted.
“I’ll be leaving shortly.”
“I think you should leave now.”
To which I regrettably responded, “And I think you should F*** off,” before turning back around.

His voice changed from inquisitive and annoyed to authoritative as he sternly responded, “License and registration please,” while getting out of the plain SUV. A subtle but crucial piece of information he had not provided and that I had obviously failed to recognize, was that he was a Florida State Trooper in an unmarked vehicle. And I was a foreigner riding a borrowed motorcycle that had just told him off. I immediately apologized and retracted my previous statement. He sauntered towards me smiling while adjusting his Smokey Bear campaign hat. I was convinced that a Florida jail cell would be in my immediate future and my one phone call would be to Harley-Davidson’s Public Relations Manager to apologize for having their motorcycle impounded. Shockingly, in a bizarre and serendipitous turn of events typically only seen in movies, he received an important call over the radio. Clearly disappointed, he returned my paperwork with a stern warning and went on his way, lights flashing. Thankful and relieved, I continued on my merry way.

Dustin never did get a ride in the biplane. But he also didn’t go to jail, so that’s a win.

Reaching Key West and the zero-mile marker for Highway 1, I toured around and took in the various sites and shot an obligatory photo of the concrete buoy marking the southernmost point in the continental USA. The Keys are a Mecca for watersports where tourists have the option to snorkel, scuba dive, jet ski, take in a glass bottom boat tour or a sunset sail. People flock to Mallory Square like moths to the flame to take in what has been hailed as the best place on earth to witness a sunset.

Key West sunsets are legendary, with good reason.

Visiting the Shipwreck Museum was fascinating as it recounts the colourful history of the island that was settled by Wreckers who would plunder merchandise and goods from ships caught on reefs or succumbed to violent storms, making it the richest city in the United States at one time. A deep-sea fisherman, bull fighting enthusiast and big game hunter, I imagine it was this adventurous and rebellious spirit that attracted Hemingway to inhabit the island with his children and second wife (of four) Pauline. Purchasing a spectacular home constructed on the highest point of the island by Wrecking magnate Asa Tift, the famous novelist’s private residence has been maintained in the same condition and it serves as a museum in his honour.

Heminway’s home has been kept just as he left it.

Featuring the only pool in Key West, his wife Pauline had it installed while he was away on assignment for an unfathomable $20,000. To put it into perspective, the entire estate was purchased years earlier for only $8,000. Upon his return home Hemingway was understandably less than impressed and allegedly took a penny from his pocket, stating, “Here, take the last penny I’ve got!” Apparently, Pauline thought it would be funny to commemorate the occasion by placing the penny in the wet cement, which can still be found there today. Along with many other artifacts, antiques and books owned by the Hemingway family that still remain to this day, the property is inhabited by as many as 45 cats said to be the direct descendants of Hemingway’s cat Snowball, many of which are polydactyl – meaning they have a sixth toe that resembles a thumb.

The Hemingway Museum property is home to many polydactyl cats, many said to be direct descendants of his cat Snowball.

Hemingway wrote some of his most critically acclaimed work in the study of that home, including A Farewell to Arms and For Whom the Bell Tolls. He may have only spent nine years in Key West but his larger than life persona evidently had an indelible effect as reminders of him can still be found all over the island. No doubt such a place left an impression on him as well; it is impossible not to take a piece of such a unique place with you when you leave. It’s a colourful place filled with eccentric characters from all over. I’m very much looking forward to travel restrictions being lifted so that I can return to explore his old stomping ground.


  1. Thanks for sharing your incredible journey through the Florida Keys! Your passion for motorcycle touring is truly inspiring. We can’t wait to experience the thrill of exploring new destinations on our favorite bikes. Keep the adventures coming!

  2. First, I appreciate the great work you are doing. I read your post completely and it was very wonderful as it provides complete knowledge and information which is very useful for us.

  3. Riding on a bike like: Harley Davidson take the enjoyment to another level. I think there is no parallels when we talk about riding a bike. It’s thrill is non explainable.

  4. Touring always give you enjoyable feel that any-other can’t and that enjoy increases If it done with your favorite motorbike. Thanks for sharing you enjoyable moments with us.

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