FLORIDA: End To End On Motorcycle

Jacob and I recently rode our motorcycles from Pensacola down to Key West. Jacob on his Honda Shadow; me on my Harley Sportster. One end of Florida to the other. Stayed off the Interstates as much as possible. It's a trip I had done before, back in the '90s, on a different Sportster, with my friend Jim on his bike (also a Honda very much like Jacob's).

During the trip down and back, we got rained on a lot. Mostly, we'd either run into isolated rain showers or we'd be just skirting the edge of them. We'd packed rainsuits, but it seemed silly to stop and put them on for the short a time that we'd actually be in the rain. So sometimes we'd stop and take a break before we got too close, and other times we just endured getting wet for a bit, only to dry off (more or less) when we came out the other side. At least getting rained on cooled us off. Good Lord, was it hot! And despite what you might believe, being on a motorcycle at 60 mph in 90 degree breeze is no picnic. You get dehydrated as hell.

Rain ahead. We saw a lot of this, going...

...And coming home.

To get to Key West, you go to Miami and then travel 127 miles down U.S. Route 1. It's basically the same route as the old Overseas Highway, which itself was built in the late 1930s on the roadbed of the Overseas Railroad which was completed in 1912 and destroyed by a hurricane in 1935. Some of the original parts of the Overseas Highway remain to this day, used as fishing piers now. It is interesting to walk on these narrow two-lane bridges, thinking about how big cars were back in the 1940s and '50s. The head-on collisions at night must have been horrible. And this was long before we had airbags, telescoping steering columns and medevac helicopters.

Here's the old bridge as viewed from the new bridge.


Look how narrow the roadway is. In the old days, the bridge was maybe a foot wider on either side, since the concrete guardrail might not have been there (see pic above). Even so, the roadway was only 12 feet wide, and that's awfully narrow. The speed limit must have been very low - and you know people obeyed it. Suuuuuure, they did.

The old bridge looks plenty stout. Obviously, these structures have survived many hurricanes since the 1930s.


It is an interesting drive to Key West. The road is wider than in the old days, but not by much. You alternate between long bridges and short stretches across islands as you hopscotch your way down. There are often periods where there is water on both sides of you - even when you're on "land." Makes you realize how vulnerable this place would be in a hurricane.

We stayed at a hotel called the Banana Bay Resort. It was a nice place, right on the water (although had no beach), close enough to downtown but not on the strip of typical chain motels. Not too expensive. Plus, the pool/jacuzzi were supposedly "clothing-optional." But there were very few people in the place while Jacob and I were there. Hardly anybody besides us was ever at the pool, and everyone kept their swimsuits on. Oh well.

Here's the pool during the daytime.

And here it is at night. They had a cool light inside the pool that changed from blue...

...To green. Neat! (Well, I'm easily entertained - what can I tell you.)

Key West is Scootertown. The streets are narrow, parking is very limited, and getting around in a car is tough. There are tons of bicycles and little scooters for rent, and everyone seems to have them. Because of this, there's plenty of scooter parking. And since our motorcycles fell into that category we never had any trouble finding places to park.

I first started coming to Key West in the late 1980s. At the time, I was partners in an airplane with which we did sightseeing tours in St. Thomas, U.S.V.I. I joke about the experience, saying that during the year we were there we lost our shirts but we got great tans - both of which were true. Retreating from the V.I. humbled and broke, we leased the plane to a guy in Key West who ran a little charter service (and suddenly the plane started generating income for us!). This worked out great for a couple of years until the guy crashed the plane, which put an end to that venture (and him, sadly).

Key West wasn't quite as much of a tourist trap back then. It was still pretty quaint and had some local charm and flavor. And it was a WHOLE LOT gayer. Now, it's just a bunch of foreign touristas clogging everything of even passing interest. Ever-entrepreneurial Americans have figured out various ways to gouge them. The gays seem to have found somewhere else to go.

Key West is not really know for its great beaches, although you'd think it would be. Above is Smathers Beach.

And since Key West doesn't have much of a beach, there are really only two things you must do: Go to the southernmost point in the U.S. and have your picture taken, and hang out at Mallory Square at sunset.

Here's the Southernmost Point. That crowd of people - mostly foreign tourists - are lined up, patiently waiting to get their picture taken in front of the monument. This was unacceptable to us, so we had to devise a "workaround."

The workaround consisted of Jacob standing up on the curb wall. Only, the guy in the orange shirt in the background wouldn't move. I was, like, "Hey buddy, get the hell outta my shot willya! Dontcha unnerstand English?" It turned out that he did not.


It used to be just a local tradition in Key West - celebrating the end of the day, watching for the green flash as the sun dipped below the horizon. The locals would sit on the pier, watch the show, then applaud when it was over. Gradually, the word got out about this and the tourists came a-running. Now, Mallory Square at sunset has become a circus. There are all kinds of street vendors and performers of varying "talent"...all of whom "worked" for tips...all of whom had "tip jugs" of some sort. One guy actually had trained his dog to circulate and take dollar bills from people. At least, we hoped nobody thought to give the guy his tip in coin. He'd have to wait a while to get those, I suppose.

Above, the teeming masses gather to gaze at the phenomenon of...a sunset. Okay yeah, Key West does have some pretty cool sunsets, but so do plenty of other places in the world.

Above: Your humble reporter and his favorite riding buddy: Me and Jacob.

I like the shot above because the little island looks like an aircraft carrier with a thunderstorm overhead.

Jacob on the pier just after sunset. Check out the stenciled warning just to the left of him. "NO SWIMING." Not too bright, boys.

I mentioned that Mallory Square becomes a circus. The picture above is of just one of the street performers: a tightrope walker just beyond a local artist selling his photographs. Just as I took this (non-flash) shot, the tightrope walker was obviously distracted by someone's video camera. I heard him yell, "Get that goddam camera light out of my eyes!" Classy, these street performers, classy.

In addition to Mr. Foul-mouthed Tightrope Walker there was a sword-swallower, the requisite human statue, and of course musicians of all kinds. Musicians?

Here is a guy we referred to as "guitarman." He wasn't very good. And he was sitting very close to another street musician playing...I think it was the bagpipes. An odd cacaphony. Guitarman had the usual tip bucket. Attached to it was a dollar bill in bait. But notice that there is writing on the bucket. Let's take a closer look!

Tips expected?! Why I oughtta... At least he had the good sense to add, almost as an afterthought, "...and appreciated."

The other side of his tip bucket had a more subtle message that despite his single dollar bill tip bait, a $5 tip was "good karma." The three nights we were there, we did not see anyone investing that much in their karma. In fact, we didn't even see anyone invest in so much as a dollar's worth of karma. We sure didn't. We hoped he had a day job...one that he was better at than his night job.

Guitarman wasn't the only marginal musician on the block.

These guys were strange. One of them was playing a xylophone of some sort, while the other was playing some PVC pipes cut to different lengths to make different notes. They were pretty good, but they only played three songs, one of which was the theme from the old video game, Tetris. We sat and watched them for a while, desperately wishing they knew more than just three songs. They never had much of an audience.

And finally...finally!...there is one thing everyone must do when visiting Key West: Get their picture taken outside of Sloppy Joe's Bar, the purported hangout of one Ernest Hemingway. Jacob knew neither of the bar nor the man.


Anyway, that was our trip. We got rained on some more on the way home. We stopped off in Tampa and visited our friend Gene who was house-sitting for his sister. We spent a week on our motorcycles - I logged 1,923 miles on mine. Our asses were pretty sore.

To see all these photos and more, you can check out my Facebook page.