Laughing Our Way To Key West, Bike Tours Bring out the Best

By Bill “Knucklehead” Plock

This is not the story I thought I would write when I decided to join the “Knuckleheads” bike tour from Naples to Key West Florida. The Knuckleheads are group of men from all over the country connected in various ways to biking. Some in the biking industry, some not, but in total 10 of us rode 285 miles accompanied by our affectionally known “church van” leapfrogging to set up the best aid stations ever. Coronas, White Claws with “vodka floaters” and Oreo’s at ten in the morning should be on all rides right? 

The reality of the story was this was a fact finding ride to understand the feasibility of making it a tour like Ride the Rockies or RAGBRAI but on a smaller scale. We definitely succeeded in flushing out some ideas on the best route, the best stops and how to make it fun. 

The knuckleheads

The story I thought I would write would be inspired by sweeping ocean vistas on causeways between tropical islands with imagined Jimmy Buffet songs billowing from every fruit stand and bar. Maybe occasional alligators would attempt to thwart our progress as we rode the Tamiami Trail through the Everglades in balmy weather with forgotten sweat pouring from my head. I got the sweat part right. 

Sure some of that happened but the views of the water were actually few and far between, the alligators were in the canal running parallel to the ridiculously flat, straight road and clearly not interested in us. There were panther crossing signs that got me excited to possibly see one which of course never happens. Really what I saw were miles and miles of densely packed mangroves, some strip malls, cars, motorcycles, the back of the wheel I was following and remnants of the eight wonder of the world (more on that soon). 

The Mangrove Tunnel with Dave Edwards (owner of Primal) taken by Percy pulling this train

But the story, like most bike tours I have done, is the people you ride with, the ones you meet and the ones you learn about who made the history of where you ride. This might’ve been amplified even more in Florida as there were no epic climbs or crazy summer snowstorms to battle or rip roaring 50mph downhills to dominate the daily download at the bar. 

But what sticks in my brain; crazy laughing, amazing conversations, clinking glasses, tantalizing food, rest stops under palms trees, on beaches and in local bars. The smell of distant tropical smoke and the spin of my wheels on smooth pavement not pock marked by freeze cracks. 

I will never forget the discovery of a rich history and culture unlike anywhere in the United States. I also will never forget so many characters we met. 


Twenty minutes after landing, I met Desiree, the exuberant bartender who took a sneaky selfie before taking a picture of us so we wouldn’t forget her. Nigel, from England who was a retired boxer and a helluva biker who joined us for part of a day. Q, this bartender at the La Te Da in Key West who slung STIFF drinks like a lost cousin to everyone in the bar belting out one liners to go with his perfectly made “skinny white bitch” mostly pure vodka drinks.

The Crew at Mo’s

It was Jimmy, a man who lost an arm and a leg but paddled everyday to his favorite bar in Key Largo, Snappers. He asked me if I had kids and when I said yes, he looked me in the eye with a huge smile and said, “you have people.” For he had none. I was grateful for that reminder. It was a Haitian couple who opened Mo’s, a small neighborhood restaurant, 17 years ago with the best snapper I ever ate. We sat on vinyl chairs with tables of formica in an atmosphere you might expect at a diner in Iowa but with some of the best food in Key West. The authenticity was only outdone by the joyous vibe this couple oozed born from hard work, undoubtedly a tough road to success and genuine interest in treating their guests like family. 

Kevin Pfaff (driver) with Dave Edwards and Pat Mayben of Primal

The story started on the West coast in Naples winding through streets with homes well north of five million dollars only to spend the night a few hours later in the heart of the Everglades at Everglade City with homes built on stilts and clearly rough and tough with years battling hurricanes. The toughness of that town impressed me much more than the glitz of Naples with plentiful Italian sports cars and wealth created somewhere else. In Everglade City golf carts and pickups ruled. The golf carts were not for golf. They were well used for carrying fish from the docks and ice from the only store in town—a busy Circle K. Everglade City is not a town you go to visit. There are no shops selling trinkets and t-shirts. It’s a town with a purpose centered on fishing and airboat tours. But it’s cool with a couple of great restaurants serving the catch of the day. At an open air bar at the Diving Pelican you will understand these people work, live and play here and respect the harvest of the Everglades and a cold beer and a DJ that gets them to the next day on the water. Oh and we and won the contest for traveling the furthest to have a drink under an 18 foot stuffed alligator. 

Thinking of the ride “across Florida” the next day sort of scared me. I thought I might fall asleep. Riding flat, like super flat roads is hard. You never get a break. You don’t shift gears, you don’t brake. It’s almost like riding a stationary bike. I gain more elevation riding on the nine mile Clear Creek trail from Arvada to Golden, than the entire 285 mile ride in Florida. But thanks to our driver Kevin and strategic stops along the infamous Tamiami Trail, the original alligator alley, the tunnel of Mangroves flashed by and occasional stops to see alligators made it memorable coupled with fun rest stops in wide spots in the road under the palm trees.   

Once on the East side of the state the ride changed. It quickly went from rural to urban in Homestead; home to massive fields of potted plants destined for Home Depots and Wal-marts. Then to the keys, the tropics and feelings of Jimmy Buffet, Ernest Hemmingway and a new character to me, Henry Flagler. Wait who? Henry Flagler? 

Unless you love history you might not know him. He is The Godfather of Florida. The man who pretty much put Florida on the map. He was co-founder of Standard Oil with John D. Rockefeller and poured his wealth into developing Florida by way of his railroad, the Florida East Coast Railway. He built massive hotels in St. Augustine, Palm Beach and Miami and made it a destination. 

In 1912 he conquered one of America’s last great frontiers by connecting Key West to South Florida. His vision built Miami from a mere fishing village of 500 in the 1890’s to over 20,000 when he died in 1913. 

Seven Mile Bridge

1906 he set his sights on Key West. He was trying to be pragmatic and take advantage Key West’s deep water harbor and the soon to be completed Panama Canal. He envisioned Key West as a major port and planned to profit from massive freight moving up the East Coast. Ultimately for a variety of reasons, including a hurricane in 1936 that literally blew trains off the tracks, his vision failed long after he died. But his dreams live on. If you care to understand this story in detail, the book “The Last Train to Paradise” by Les Standiford is a great read. 

It was his obsession to connect to Key West that made our ride, in theory, even possible. Flagler’s company toiled for years cutting through the mangroves, saw grass, coral and limestone to extend their tracks to Key Largo from Miami. But with a 100 miles still to go, and huge gaps of water between islands, engineering feats popped up like key lime pie stands do today. The bridge connecting Marathon to the lower keys, called Seven Mile Bridge was called the 8th wonder of the world and finished in 1912; the same year the Titanic sunk and New Mexico and Arizona became states. Key West, Florida’s largest city for decades in the 1800’s was finally connected  to the rest of the state. Much of the United States was flourishing and developed by then, but Florida, particularly South Florida was arguably one of the last great frontiers. And to this day with hundreds of square miles of formidable swamps, it’s still mysterious and harbors a wide swath of life, interests and people.  

Local artist painting the end of the road

Riding bikes is about discovery; discovering yourself, others, places and history. Riding with a group of friends, or soon-to-be friends to Key West and the Everglades reinforced the sense of wonderment and adventure. For generations people have flocked to the Keys to feel the allure of the topics unlike anywhere else in the continental U.S. For us to make it to the end of Highway 1 only sets the stage to finding other roads and discovering the route to their roots. 

Architects of our trip; Dave Edwards and Dieter Drake

For 10 lads born in the last half of the 20th century to discover the magic of the Keys was worth our own toil on the straight roads against the wind. To feel the history. To experience the people here, to learn of new tales, different lifestyles and to gaze at the open ocean all on a bike paints a beautiful picture my mind will never forget. 

If you have never done a bike tour there are many reasons to consider one that has a lot more to do with everything other than the ride. You will never forget the camaraderie you feel and the places you explore. 

The laughter. The friends. The characters. The history. The food. The drinks. The accomplishment. All of it. 

Did I mention the laughter? 

Bill Plock at the end of the road in Key West

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  1. Pam

    Bill. So well written. I feel like i just rode to Key West. Cheers!!

  2. Rob Ladewig

    Spent 3 great years in Key West with the Air Force. The seven mile bridge run is still my favorite

  3. Bob D

    I miss the smooth unbroken asphalt of South Florida roads and the massive, fast group rides that a flat state like FL allows for. As a Denver transplant from Miami I’ve found it difficult to adjust to Colorado group rides that splinter within the first 5 miles to leave you pedaling alone for long stretches. Thank goodness for all the blistering fast downhills that allow me to catch up!


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