22. The Overseas Highway

The Overseas Highway: The 113 mile stretch of US 1 that runs between Miami and Key West is a modern marvel and a treacherous gauntlet of wind gusts when driven in a thirty year old German bread box. Thankfully, most of the original 1920s structure has been abandoned (center), in favor of a slightly wider two-lane run that better accommodates today’s trucks and giant motorhomes (far right).

After forty-two bridges and several hours of incredible Caribbean vistas, the bus rolled to a stop at the end of US 1, the southernmost point in the continental United States, only 90 miles from Cuba. Amy’s in New York now with her family, so I took this long trip solo. Halfway through, I broke my “no giving rides to bearded drifters” policy in favor of an hour of bizarre conversation with a 35 year old wanderer named Caleb. He was like any of the thousands of restless hippies, drifters and dreamers who help populate the Florida Keys – Deeply tanned, relaxed and waiting to hear back about an “artist permit” that would allow him to sell crafts on the streets of Key West. He approached me at a gas sation and asked for a two mile ride. I ended up taking him forty.

Sloan: How long have you lived here?
Caleb: On and off since I was nine. I can’t stay put, man. The old timers all call me Driftwood.
Sloan: I wish I had a nickname.
Caleb: Anyway I just got back from 6 months of riding freight trains from here to Denver. You ever ride freight trains?
Sloan: No, I don’t think so.
Caleb: This was my first time, it was wild. We hooked up with some hobos that taught us how not to suffocate in the really long tunnels.
Sloan: I never would have thought of that!
Caleb: Yeah, it was wild. Hey, do you smoke bud by any chance?

I told him I didn’t. Not anymore. Not since I was a younger man. Not since I bought this 1977 VW Bus, because I mean, c’mon. How obvious would that be?


  1. The Orion Wayfayer says:

    Curious notation: Dick Cheny fell off this while fishing, and after hearing of his pending grandchild via his “don’t ask, don’t tell” daughter’s shananigans!!!! Oppss! Life goes on, with or without the bridge viceprez!

    Monesterial Mikie