Tales Between Trails: Florida Keys to Maryland

Wednesday, December 25th – Friday, December 27th, 2019

 After a long hike, we were rewarded with a very nice Christmas, Florida-style! Key West was lit up and beautifully decorated. The tourists were filled with cheer, and by cheer I mean booze. Lots and lots of booze!

This was our first time here as sober people. The way I feel about Key West now is the same way I feel about New Orleans. It is WAY more fun with a beer! Don’t get me wrong, we still had fun ‘people watching’, but it just isn’t the same.

We got up before sunrise the next day to get proper pictures by the buoy. One without an angry mob of tourists surrounding us. After checking out of the hostel, we wandered around.

The locals didn’t know what to think about us. The homeless population was even more skeptical. We were too clean to be homeless, but too grubby to be tourists. This perplexity is not new to us. We get the same baffled looks from everyone whenever we hike, but by no means does it ever lose its amusement!

One homeless guy was running around with blue chalk drawing arrows on the sidewalk. He grinned at us and told us about a cookie eating contest. This was, of course, unbeknownst to the business hosting it. They weren’t open yet, so we unfortunately missed out on their reaction.

That evening, we caught a show by the Cat Man and his hoop-jumping kitties. This man was clearly insane, but we were thoroughly entertained.

This was our final night in Key West, and we didn’t have a place to sleep for the night. So we stayed up late, people watching until it quieted down. Some locals and homeless still didn’t know what to think of us. On occasion, one would approach us, asking us questions. Wondering why we were just sitting on the sidelines instead of getting on the field. When we’re not out hiking, I guess you could say we’re pretty boring! After witnessing a bar fight and police investigation, we wandered off. If we were going to sleep somewhere, we wanted to get closer to the airport.

We walked a few miles in the direction of the airport before hunkering down on some picnic tables by the beach. This would be short lived. Our snooze was interrupted by a group of teenaged boys who were planning to drink and smoke where we slept.

“Whoa! Hold on guys, I think someone’s over there.”

We sat in silence. Silence is creepier. Spooked by our motionless silhouettes, they returned to their car. One of them acted like a tough guy.

“I should throw a bottle at them.”

I rolled my eyes. Since we had been discovered and the mosquitoes were horrendous, we continued walking towards the airport and waited out front. We’d receive one last unkind gesture. The security guard scolded us while we waited for the airport to open up for business.

“Don’t come in here before 5:00. We aren’t open. Anyone coming in earlier works here.”

We complied at first, but then went against his wishes after a number of nicely dressed, non-employees hauling their luggage entered without question. If I were wearing Prada and carrying a Gucci bag rather than wearing hiking gear and a backpack, I’m pretty certain we would have been treated differently.

That would be our only annoyance for the day. Going through security went smoothly, as did our flight back home. Time to go back to work and back to reality! At least until our next big adventure. We had huge hopes for 2020. As you know, things didn’t go as planned. For anybody.

Jump Ahead to Tales Between Trails: Maryland to Colorado

Jump Back to Road Walk to Key West: Chapter 10


Start from The Beginning

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