Scout’s Honor Cross-Country Motorcycle Ride Part 7: Key West

Key West - Papa Dobles & The Southernmost Point

Scouts Honor Ride, Miami to Key West
The highway that leads from Miami to Key West is only 168 miles long, but can take upwards of five hours.©Motorcyclist

As far as we’re aware, no one has ridden Indian's new Scout or Scout Sixty across the country, until now. And we're sort of excited about that! Being the first at something like this is similar to owning a roadside oddity, in my opinion - maybe the world's biggest jelly bean? It's fun to say, you might even impress a few people, but it's really nothing to bank a career on, or be too proud of. It does make for good bar-stool banter, though, and we're happy to have it. So when we rolled into Key West fifteenish days after we had departed the other side of the States, we both said the same thing over our Sena headsets: "I can't believe we're already at the end of this adventure!"

Scouts Honor Ride, Key West
Where the sea and the sky become the same color and the road ends in the middle of the ocean, Next stop: Key West!©Motorcyclist

My father raised me to be a man interested in all sorts of things. Books, bikes, baseball and everything in between. He was a man who himself enjoyed a wide variety of activities, and strives to spend time around those that did similarly. Ernest Hemingway, of course, was just the sort of man my father would have fallen in with given the chance. And so as a child, my father encouraged me to read his work, to investigate the kind of guy he was and then trace his steps in strange ways. I've visited the home in Idaho where he shot himself with an Abercrombie & Fitch shotgun, seen his apartment in Paris and drank rum at his favorite bar in Venice, among other things. It's not an obsession, or even a hobby; it's just something that seems to happen. An excuse at times to visit a place, find a decent drink or explore a city that I might otherwise see only through the lens of top 10 lists and Google reviews.

Scouts Honor Ride, Florida architecture
Classic Floridian architecture – wrap-around porches, beams that keep the building above ground and trees that surround the house and provide some much needed shade.©Motorcyclist

When we came up with the idea to ride Indian motorcycles across the country, my first thought for a final destination was not Daytona Bike Week or South Beach, but instead Hemingway's home in Key West. A place I'd read a great deal about that clearly inspired the man; he wrote 70 percent of his published work while living there. And Kyra was all about the idea, so there wasn't anything left to discuss. We'd cross the country the slow and southern way and eventually wind up at the Southernmost Point of the contiguous United States, then drink Papa Dobles and sink our feet into the sand. Done and done.

Scouts Honor Ride, Sloppy Joe's, Ernest Hemmingway
Sloppy Joe’s, the infamous establishment where Ernest Hemingway imbibed all too often.©Motorcyclist

The fact that our country stretches this far into the sea, that you can drive the distance in just a few hours, escaping the madness of Miami for the quiet of the Keys, is really incredible. We had been out late the night before. You haven't seen anything until you've seen South Beach on the first Sunday of Spring Break, and so our first stop was a small Cuban coffee joint a few miles south of where we had stayed the night before. 160 miles is all that separates Miami and Key West. The highway runs due south with one lane headed in each direction. It can take more time than it should since speed limits are well below the 75 mph average we'd grown accustomed to across the country. But it's beautiful, and the time seemed to slip beneath our bikes.

Scouts Honor Ride, Key West
Some of the Key West residents prefer to preserve Papa’s history a different sort of way.©Motorcyclist
Scouts Honor Ride, Ernest Hemmingway studio
Inside the writing studio of Ernest Hemingway – preserved as it was the day he departed Key West.©Motorcyclist

Of all the Keys, the one at the end is what we were after. That's not to say we didn't see things along the way we wished we had more time to explore, but time was a thing we were running out of on this trip, and with only two nights at the end, we wanted to take full advantage of our first day off the bikes in more than a week.

Scouts Honor Ride, cruise ships
Cruise ships and small sailing vessels could be seen crisscrossing the south coast of Key West, a reminder that there are other ways to get here beside a bike. But that wouldn’t be any fun, would it?©Motorcyclist

Unless you’ve visited Key West, you haven't seen this color before. Where blue and green and white mix with the sunlight reflecting off the surface and the beige colored sand only a few feet below. The ocean is an incredible thing. It can be so beautiful and yet so deadly, so vast and yet so confining. Our ride down was memorable only in that what we saw along the way astonished us. And it didn't stop until the road did, in Key West, where Hemingway lived and millions have visited. Where the resorts are twice the price of just about anywhere else and the streets are lined with aquatic activities being sold in package deals fit for America's nuclear families.

Scouts Honor Ride, Key West swim
Our first swim in the sea was a wonderful one. The water was an incredible color, and the temperature was just about perfect. A fitting end to our adventure.©Motorcyclist

Kyra had arranged for us to stay at the Ocean Key Resort. She had worked her magic, which allowed us to afford more than one night, as well as allotted us two free breakfast tickets. She ate lobster both mornings and drank orange juice and coffee and brought the banana bread back to our room. Crafty gal. I don't go in for leftovers, but that banana bread was just as good three days later. Situated at the end of the island at the end of the road, we were a stone’s throw from Sloppy Joe's, an old haunt of Hemingway's, as well as walking distance to all that Duval Street has to offer. Which is nothing we were not interested in. We unloaded the bikes, got all googly-eyed when we saw the room we’d be staying in and then slipped into shorts and hit the streets on foot.

Scouts Honor Ride, Key West islands
Small islands offer serenity for those that can afford it.©Motorcyclist

Unbeknownst to us, we were in Key West the same week Spring Break had begun, as well as the last few days of Daytona Bike Week’s 75th anniversary. So instead of retirees and families of four on vacation, we got leather-clad Harley riders and 20-somethings looking to get smashed on mixed drinks at any and all of the bars down Duval. Unfortunate, yes, but when life gives you lemons, er, drunk idiots, you just need to be willing to walk. And walk we did. From one end of the island to the other. We found a quiet little café called The Café that served mostly vegetarian meals and damn fine draught beers, among other things. Inside was a 75-year-old man, tanned and wearing a bright blue Reyn Spooner shirt, who explained how he’d ended up living in Key West for nearly 19 years; a place that was supposed to be nothing more than a short stop on his sailing adventure around the world. We then ate soft-serve with sprinkles, as we do, and walked the rest of the way across the island to Fort Zachary Taylor where we traded khakis for aquatic breeches and went for a swim in the sea. Afterward, we stopped at the Southernmost Point, snapped a photo and moved on. The next day we explored the island further afoot and eventually found ourselves inside a small establishment frequented and full of locals whose happy hour consisted of a cocktail menu and a pair of dice. You roll a one and your drink is a dollar, a two and your drink is two-dollars, a three and its half-off. Anything higher and you pay full price. Hot damn it was fun, and after three cocktails each we were feeling feisty and only 20 dollars deep (Kyra is clearly a lucky lady). The night ended, like all good nights, with a late meal and dessert.

Scouts Honor Ride, downtown Key West
The sun drenched streets of downtown Key West, a place where classic and contemporary architecture clash at times.©Motorcyclist
Scouts Honor Ride, Key West palm trees
Boats, tall palms, blue skies and sunshine. This is what we’d been waiting for!©Motorcyclist

You’re probably wondering what the hell happened to Hemingway’s house. Did we visit? Was it interesting? I suppose I left that out when describing the series of events that took place during our two-day stay. My bad. We did visit, and it was interesting. There were six-toed cats all over the place and the house is set up with the same furnishings as when Hemingway had it. Honestly, though, it’s the kind of place you should see for yourself. I guess ultimately that’s the response I would offer anyone that asked me about this adventure, especially Key West. You’ve got to go. See this stuff for yourself. Save up the vacation days or quit your job or just call in sick, I don’t care, but don’t waste too much time. Because wherever you are, whatever you’ve seen, Key West will still make your head spin. I understand why Hemingway was here. It’s like America, but better.

Scouts Honor Ride, Florida
Our eventual ride off the island was bittersweet. The highway provided epic scenery, and the southern climate was about as good as it gets. Until next time, Florida!©Motorcyclist