Harley-Davidson in the Easy, Breezy Keys

Harley-Davidson Key West Tour Road King
Road King and scooters

You don’t feel the full effect of Key West until you leave. As I strike out with my buddy Jim Miller along US Route 1—a causeway connecting the island to Florida’s mainland—I consider the Gulf of Mexico and its ever-changing palette of pastel greens and blues. Like the clouds that hang lazily in the sky, we are in no hurry. A refreshing ocean breeze flows through the vents of my jacket, and I feel perfect peace.

The trip was Jim’s idea. He had called in February, when my North Carolina home still endured the short, dark days of an icy winter. “Why don’t you head down here and come riding for a few days?” he asked.

We met in Florida and went straight to the rental office of Bruce Rossmeyer’s Daytona Harley-Davidson, where we signed the requisite forms and received a thorough demonstration of our mounts—a Harley-Davidson Road King and a Heritage Softail Classic. Armed with cable locks, insurance forms, and emergency contact information, we picked up I-95 and gunned the Harleys southward. We dialed in a comfortable 70 mph, passing a landscape of flat, open country peppered with cabbage palms, skinny pine trees, and intermittent billboards which offered the services of personal injury attorneys.

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New Smyrna Beach became Cape Canaveral, and then we joined the Florida turnpike at Fort Pierce. Before long, the traffic of Miami interrupted our idyll, but—clear of that hectic metropolis—we resumed our relaxed pace. After passing peaceful tree-lined waterways where fishermen took shelter from the late afternoon sun, we found US 1. Homestead came and went.

Harley-Davidson Key West Tour Shell Shack
The Shell Shack

As the moon rose, we halted at a rustic dock on Key Largo, where we had planned to end the day’s journey. We found no accommodation there, but had better luck a few miles to the south at the Tropic Vista Motel in Tavernier. Its manager, Ronnie Dilig, had one room left. Soon Jim and I were enjoying meals in her restaurant, and afterwards Ronnie told us tales of her two decades in the hotel business on the Keys.

At the waterfront the next morning we watched schools of fish beneath the boats and big pelicans lumbering overhead. Though tempted to remain, we knew it was time to saddle up and continue to Key West.

Shortly after passing through Marathon Key, we rode onto the famous Seven-Mile Historic Bridge and the world around us entered what seemed to be a new dimension—it was as though we were riding through a fish eye lens. The ocean bent around both sides, and the horizon perfectly separated the sky from the sea.

In the distance, a few sailboats leaned into a strong wind as they plied their way across waters dotted with sandbanks and small islands. I sank into the Harley’s luxurious seat, stretching my legs out on its roomy footboards. The big engine pulled smoothly and strongly, and each mile I covered removed a layer of stress.

Harley-Davidson Key West Tour Casa Marina Resort Overhead
Casa Marina Resort

We arrived in Key West—a corruption of its Spanish name, Cayo Hueso, or Isle of Bones—around mid-afternoon. Our destination was the Casa Marina Resort, Key West’s oldest and largest resort, built by Henry Flagler in 1921. The island’s relaxed dress code meant that a couple of riders attired in leather jackets, jeans, and bike boots did not raise an eyebrow in the lobby of its finest hotel. After checking in, I pulled back the curtain in my room and gazed at swaying palms, white sand, and the gentle ocean.

It was our first night in town, so we headed down to Duval Street—a short stroll—to check out its famed nightlife. We stopped at Capt. Tony’s Saloon, made famous by Ernest Hemingway as Sloppy Joe’s. In the corner of the dimly lit bar—notable for its ceiling covered in license plates, business cards and a colorful selection of women’s underwear—its elderly owner held court with a small, attentive audience.

At 88 years of age, Anthony “Tony” Tarracino is something of a local icon. By his own account, he has occupied himself as a gunrunner, mercenary, bootlegger, gambler, saloon-keeper and womanizer. He said he fought for Fidel Castro, discovered Jimmy Buffet, and once became the mayor of Key West with the singer’s help.

His three marriages produced 13 children, and he proudly informed us that his youngest son was graduating from high school with two of his granddaughters. Ever the ladies’ man, he soon redirected his attention to an attractive woman. As we were exiting the bar, Tony’s crackly voice followed us into the evening air. “Make every heartbeat count,” he called. After this story was written, Tony passed at age 92.

I rose before dawn, in time to observe a pink and violet sunrise. We had only a day to spend in Key West and a visit to the southernmost point of the United States—only 90 miles from Cuba—has a few obligatory stops, including Hemingway’s house, and a cold drink at Ernest’s Cafe. There, in the shade, we settled onto barstools.

Harley-Davidson Key West Tour Kayaker
Rick and his Kayak

We met Rick, a dedicated cyclist who tows his kayak behind his bicycle. Rick told us he hadn’t used motor transportation in eight years. “We have unheard levels of tolerance in Key West,” he beamed, from behind John Lennon glasses and a wooly beard. “It never gets cold, and there is plenty of work to be had. If you are willing to show up sober and on time, you are better than the next guy.” I wondered whether I could give up riding motorcycles to live on an island less than four miles long and two miles wide.

On nearby Stock Island we had lunch in the warm, lazy air at the Hogfish Bar & Grill. We heard more tales of smuggling and gunrunning and looked at pictures of Jimmy Buffet’s last visit. Well-used shrimp boats bobbed on the tide, sea birds swirled and dived, and a light wind whistled through guy wires. The atmosphere held us spellbound.

Stopping on Cujo Key to check out the tethered radio blimp that broadcasts to Cuba, Jim and I found a shady spot in the mangroves to enjoy the cool ocean breeze and the sound of water lapping against the shore. When the sun began to sink, we mounted up and made our way back to a little café where we indulged in our final Key West sunset. I experienced deep contentment as another surreal day concluded.

The next morning we rode the Harley-Davidson Road King and Heritage Softail Classic rental motorcycles back to Daytona Harley-Davidson and returned to our regular lives, but—in the golden light of Key West—Daytona was a million miles away.

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Photography by Tom Riles

Harley-Davidsons Touring Key West Gallery