Places I Have Sleepen: The Finest Cardboard Box in all of Key West

Late December 2008.  I had been camping out in the Everglades for about 2 weeks and thought it close enough to make a jump to Key West for a Saturday night.  Figured there’d be more going on there than the lake I was camping next to.  So, I packed up some vittles and rain gear then headed off.
It was a nice drive.  Ocean breezes.  Bridges which were miles long.  The only place I was interested in visiting was Captain Tony's.  Not only is this where Jimmy Buffet got his start, playing songs on stage for beers, but it’s also where Ernest Hemingway used to get some of his drinking done!
Unfortunately, the place was dead.  I mean D-E-D dead!  I had a couple more beers thinking that it was just too early in the night but I’m pretty sure there were more alligators in that lake back at my tent than there were people in this bar.  I walked out and determined to ride back in an hour or two after I had sobered up.

My good friend Edward

So, there I was standing on the street corner, people watching when this dude comes up to me.  Kinda raggedy-looking.  I saw he started to ask me for money but, then he stopped, looked me up and down with a puzzled look on his face – mind you, at this particular time I had been on the road for about 3 months and camping in the Everglades for nearly 2 weeks so needless to say I wasn’t looking or smelling my best perhaps.  Anyway, after looking at me with a confused look on his face he asks me, “Hey man.  Are you local?”  I smiled at him.  No man!  I’m traveling.
I told him about how I just got out of the military a couple months ago and was riding my motorcycle across America.  “How long?”  I don’t know.  Like a year or so.  “What are you up to now?”  Well, it’s dead here so I’m heading back to my campsite once I’m sober.  “What?  No.  This place is cool.  Let me show you around.  My name’s Edward.”
So Edward and I picked up a 6-pack and did a walking tour of Key West.  Did I get to see six-toed cats or the southernmost tip of the US?  Nope.  I got a very personalized tour of Key West.  The kind you can’t buy.  Well, actually, I’m sure that you can buy a tour from a homeless person but nobody’s thought of that yet.
First stop was the photo I’ve included.  The Key West Hysterical Preservation Society posted a marker making note of special places in history where nothing happened.  I loved it.  Next Edward showed me where him and his homeless buddies usually slept which was alongside a dock which was roped off that evening.  There was a cruise ship docking there the next day and I guess Key West didn’t want Edward and his drifter friends as the welcoming committee so they had to relocate.  He then took me to their secondary slumbering location.  It was just behind some old buildings.  Nothing to note of it except that they couldn’t stay there anymore either because recently kids were coming up while they were all asleep and throwing rocks in their faces.  What the hell?
So, it was about that time that we ran out of beers.  He took me back to the bars and we met up with a couple of his friends.  We stood outside of one bar which had a live band playing inside.  The music was loud enough and we were positioned right next to the large window to enjoy the music without paying the cover charge.  So, there on the sidewalk and in the street we danced.  The bartender noticed us and gave Edward a nod.  About 5 minutes later a table full of people got up and left.  The bartender only partially bussed the table.  Over he came to the window and set the half full beer bottles on the window sill.  Edward and his cohorts grabbed ‘em, divied them up amoungst themselves (I told Edward he could have my share) and they chugged those beers faster than you could take your sandals off.
Edward was retired from the Service  as well.  He bought a sailboat and was traveling up and down the coast on it.  I never got to see it unfortunately.  He was perfectly happy in the Keys though.  The weather was perfect for sleeping out.  The friends that he had were a real community of people, closer than any neighborhood I’ve ever lived in.  Looking out for each other and always sharing their latest score.  He said they had to be down there.  Every federal government law enforcement agency had a strong presence on Key West due to the fact that Cuba was only right over the horizon.  …  I think Edward may have been the first person I’ve spent any kind of time with who wasn’t actually homeless (as being homeLESS implies a lack of something which is desired).  Rather he was homefree.  It was a new concept which was soon to define the next few years of my life.  Although I didn't know it at the time.
Well, it was getting late.  I was tired from the long ride and I said to Edward, So, where can I find somewhere to sleep around here?  “I’m tired too.  Follow me.”  We walked down the side streets and it suddenly occurred to me, Edward, do we need some cardboard?  “Yeah, there’s some right up here.”  So, we each grabbed a broken down box.  I think mine was for industrial napkins or paper towels.  We ended up sleeping in an old dilapidated parking lot next to a beautiful old school which was set to be torn down to make way for progress.
I woke up a few hours later to my alarm.  The street where I parked the bike had to be cleared by 6 for the street cleaners.  I sluggishly walked back to my motorcycle.  I passed a tourist sleeping right on the main sidewalk using a step as a pillow.  There was another guy who I later figured out must’ve been pickpocketing him although I was too groggy to pick up on it at that moment.  I just said hi to the guy and smiled as I walked on by, completely oblivious to what was going on.  I only barely beat the street sweepers to the motorcycle and rode it back to the parking lot.  It was up a one way street but I couldn’t be bothered to find the legally-correct way back.  And it was early enough I figured I wouldn’t get caught.  Made it back to my little home-away-from-home and had myself another small nap before I awoke again.  I bid Edward adieu and thanked him for the awesome night.  then hopped on the bike and rode it back to my tent site in the swampy, alligator-infested Everglades.

Cardboard boxes provide both padding and serve as a blanket as you can see Edward demonstrating here.

About a year after I returned home I gave a speech about my travels in front of a couple hundred people and included the tale of this particular night.  Afterwards I was interviewed by a reporter from the Cincinnati Enquirer.  The next day, front page of the Business Section was a review of the many speeches that were given that evening.  Mine was one of the few included and it told of how I had "inspired" the reporter because I had "lived in a cardboard box in Key West."  I'm probably one of the very few people to be mentioned in newspapers simply  because I had spent a night in a cardboard box.  I remember people being all like, "Robbie!  I saw you in the newspaper!  Congratulations...?"  I think it's great!