Harley-Davidson Baggers to the Keys

March 16, 2007
Neale Bayly
By Neale Bayly
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With 37 years in the saddle, Neale Bayly has ridden motorcycles in 45 different countries around the world. Until it was sold to Fox Sports, Bayly was the motorcycle editor for Speed Channel, where his 2013 reality series "Neale Bayly Rides" made its debut. The series documented a charity ride to a Peruvian orphanage, which his charity, Wellspring International, supports. The British-born Bayly currently lives in Charlotte, NC, and spends his free time with his two sons, Luke and Patrick, hanging out and riding dirt bikes.

Miller and Bayly don t look to worried about being shanghaied and forced to work out their days aboard a shrimp boat.
When Bayly’s riding buddy called and suggested they rent some Harleys and head to Key West, Neale traded his winter coat for riding leathers and headed south.

I don’t really think you feel the full effect of Key West until you leave. Rumbling out along US 1, the big Harley purring effortlessly beneath me, I am totally in the moment.

A look in the mirror shows my buddy Jim’s calm face gazing out across the Gulf of Mexico. Absorbing the sparkling water as an ever moving, ever changing kaleidoscope of pastel green, blue and turquoise, wisps of thin cloud hang lazily in the bright blue sky. Like the clouds, and the many local people we have met, we are in no hurry as we roll through the early morning sunlight. To my right a group of tourists hustle to the next attraction as we ride in perfect peace, the refreshing ocean breeze flowing through the vents of my jacket. In the saddle, the only place that matters is right now, and as we turn north and ride off Key West, it is destination realized.

With winter’s icy grip still holding firmly to the short, dark days of my North Carolina home, a phone call from long time riding buddy, Jim Miller, came as a welcome surprise. “Why don’t you head down here and come riding for a few days?” he asked. Sowing a seed that germinated quickly into a plan, late February saw us pulling into Harley-Davidson of Daytona and heading for the rental office. Not wanting to risk riding out of the mountains in mid winter, I had suggested picking up a couple of Harley’s and riding down to Key West.

Quickly signing a few forms, we stepped outside into the bright winter sunshine for a thorough demonstration of our respective mounts before loading our gear into the saddlebags and heading for open road. Fully equipped with cable locks, insurance forms and emergency contact information, we picked up I-95 and gunned the Harleys south. Dialing the bikes on a comfortable 70 mph, Charlie’s Angels’ look-alike lawyers offered their legal services from colorful billboards. To our sides, flat open country peppered with cabbage palms and skinny pine trees provided the only interruption to the pale blue sky as we rode through the crisp, fresh Florida air.

Bayly left the icy grip of a North Carolina winter behind for the warm  inviting waters of the Gulf of Mexico.
Bayly left the icy grip of a North Carolina winter behind for the warm, inviting waters of the Gulf of Mexico.

New Smyrna Beach became Cape Canaveral, and at Fort Pierce we left the Interstate, taking the Florida turnpike as we rolled steadily south. Here the pace relaxed, with less commercial traffic, before a hectic half-hour passing the city of Miami. Once clear of the manic commuter traffic, we passed peaceful waterways lined with trees, as fisherman took shade from the late afternoon sun. Picking up US 1, Homestead came and went and, with the setting sun burning the horizon a breathtaking array of golden colors, we pulled into Key Largo, the moon appearing as a thin slither of light in the vast sky. With the scattered clouds hanging like an artist’s brush strokes in the breathless sky, we parked at a rustic old boat dock to absorb Mother Nature’s brilliant performance.

Unfortunately accommodation wasn’t to be found in Key Largo, but lady luck stepped in as we stumbled across the Tropic Vista Motel in Tavernier a few miles to the south. Run by a wonderful lady by the name of Ronnie Dilig, she had one double room left, and we were soon enjoying an eclectic variety of food in her adjoining restaurant as Jim ate local grouper and I feasted on chicken curry. Relaxing after dinner, Ronnie regaled us with tales from her 20 years in the hotel business on the Keys since emigrating from the Philippines.

Waking up in the heart of dive central USA, we were in no hurry to leave the quiet dock behind the hotel as the warm sunshine worked its way into our bones. Large pelicans came lumbering in like WWII bombers silhouetted against the morning sun as schools of fish swam beneath the dive boats. Feeling glued to our seats, a decision was finally made to break the spell, saddle up and head on down to Key West.

The duo admires the famous seven-mile bridge before traversing the gateway to the Keys.
Bayly and bud check out the famous seven-mile bridge before crossing the gateway to the Keys.

Meandering slowly south, taking in the vast expanse of water to our sides and marveling at the color and life in the small towns sliding slowly by, a curiosity stop found us at the Holiday Isle. Posing for the ubiquitous vacation snaps, it was a little too kitschy for my liking so we wandered back to the bikes and rolled on down the road. Shortly after passing through Marathon Key we rode onto the famous Seven Mile Bridge as the world around us headed into a new dimension.

It was as though we were riding through a fish eye lens, the ocean bending around us forever on both sides, the horizon a pencil-thin line perfectly separating the cloudy sky and shimmering sea. A few sailboats leaned into the healthy wind as they plied their way across the multi-colored water, peppered with sandbanks, small islands and shadows from the clouds. In the saddle I sank into the luxurious seat, stretching my legs out on the roomy footboards, while the big engine pulled smoothly and strongly beneath me. Each mile south forced us to relax, to breath deeper, and as the sun’s warmth caused us to peel off layers of clothing, so I felt my internal layers peeling away.

Arriving in Key West, or Cayo Hueso (Isle of Bones) as exploring Spaniards named it, around mid-afternoon, we made our way straight to our accommodation at the Wyndham Casa Marina. As the oldest and largest resort in Key West, the Casa Marina has the enviable distinction of being conceived and designed by Henry Flagler. With a fascinating 70-year history, the list of famous celebrities that have graced its beautifully manicured grounds is long. Fortunately, with life in the Keys being extremely laid back, a pair of leather-jacket wearing riders in jeans and bike boots didn’t even raise an eyebrow as we checked in and headed for our rooms.

Rife with tales of gun smuggling from Cuba and autographed photos of Jimmy Buffet  Bayly and Miller stopped by the Hogfish Bar at the recommendations of a local.
Rife with tales of gun smuggling from Cuba and autographed photos of Jimmy Buffet, Bayly and Miller stopped by the Hogfish Bar at the recommendations of a local.

Pulling back the curtain in my room and gazing out at the swaying palms and white sand beach running into the gentle ocean, I could have quite easily jumped in the patio recliner and let the sound of the ocean work its magic. But it was our first night in town so we headed down to Duval Street to check out the nightlife on this world famous street. Located a short stroll from the Wyndham, we made for Captain Tony’s bar to sample a little Key West color, not knowing lady luck was once more on our side.

Stepping inside the dimly lit bar, the ceiling covered in license plates, business cards and a colorful selection of women’s underwear, there in the corner was the man himself holding court to a small, attentive audience. At 88 years old, Anthony “Tony” Tarracino is an iconic part of Key West’s illustrious history, having had the dubious distinction of being a gunrunner, mercenary, bootlegger, gambler, saloon keeper and womanizer, to name a few of his talents.

Taking our place for a quick chat we also learned he fought for Castro, discovered Jimmy Buffet and went on to become Major of Key West with the famous singer’s help. Married three times, Captain Tony has fathered 13 children, and proudly informed us his youngest son was graduating high school with two of his granddaughters. Ever the ladies man, he was soon diverted by the attention of a flirtatious woman, so we decided to use this as our cue to go and walk some more.

Exiting the bar, once made famous as Sloppy Joe’s by Ernest Hemmingway, the crackly voice of the legendary man who smoked three packs of filter-less Lucky Strikes a day for 70 years followed us into the evening air, “make every heart beat count.” Heading to the Flying Monkey on Duval Street for dinner we were about to.

Land ho! Unless Bayly s got a pair of water skis hidden somewhere  this is as far south as he can go in the continental U.S.
Land ho! Unless Bayly’s got a pair of water skis hidden somewhere, this is as far south as he can go in the continental U.S.

Up before dawn, we were certainly not wasting any time sleeping. And, as the fog of an evening of Key West style entertainment melted, so the new day arrived full of expectation and promise from the beautiful pink and violet sunrise. With only a day to spend in Key West, there were a number of things we wanted to see and do, as well as just following our instincts and seeing where we might end up. The mandatory trip to the southernmost point of the United States to gaze out across the water, where just 90 miles away Fidel Castro is still holding the reigns in Cuba; a short visit to Hemingway’s house, and a chance stop at the Ernest Café for a cold drink.

Settled on our stools in the shade, our next Key West character presented himself in the shape of Rick. A dedicated cyclist who tows his kayak behind his bicycle, Rick tells us he hasn’t used motor vehicle transportation for eight years now.

“Everybody has lost their minds in Key West and we have unheard levels of tolerance,” he beams at us from behind his John Lennon glasses and wooly beard. “It never gets cold, there is plenty of work to be had, and if you are willing to show up sober and on time you are better than the next guy.”

Wondering if I could give up riding motorcycles and live on an island that is less than four miles long and two miles wide, I scratched down directions to a restaurant Rick recommends for lunch on a neighboring Key. Riding up to the Hogfish Bar and Grill in the warm lazy air, we were soon being regaled with more tales of smuggling and gun running from Cuba, as the manager showed us pictures of Jimmy Buffet’s last visit. Battle-scarred shrimp boats bobbed on the lazy tide, as sea birds swirled and dived, the light wind whistling through the guy wires. Spellbound by the atmosphere, we finally pried ourselves away heading north a while.

Bayly spends the last day of his journey filled with contentment and contemplation.
Bayly spends the last day of his journey filled with contentment and contemplation.

Stopping on Cujo Key to check out the tethered radio blimp beaming broadcasts to Cuba, we found a shady spot in the mangroves, kicked back and enjoyed the cooling ocean breeze as the gentle water lapped the shore. And then as the sun began to sink low in the sky, we mounted up and made our way back to a charming little outside cafes to indulge in our last Key West sunset.

Relaxing in the last golden light of another magical day, the feeling of inner contentment is hard to describe while we sat waiting for evening to come. Tomorrow we needed to ride the Harleys back to the dealership and return to our regular lives, but there in the golden light of a Key West sunset, Daytona might as well have been a million miles away.

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