Our Spring Break Adventure: Key West

how to hitchhike

The Origin:

Last year for Spring break, I hitchhiked over a thousand miles, to Bloomington, Indiana and back. This year though, I was just looking to relax. Over winter break, I had completed a transcontinental adventure, hitchhiking from coast to coast. And with plans set to sail to the Galapagos and join The Peace Corps in the coming year, I really wasn't in the market for another adventure. My girlfriend, Savannah, though had other plans; she wanted to hitchhike to Key West. 

Savannah's parents frequently travel to Miami, and over our Spring Break they, along with her brother August, were headed down to The Capitol of Latin America. Originally, Savannah wanted us to hitchhike the 2,000 miles, from Clemson to Key West and back, but I convinced her that if she want to do more than just hit Mile 0 and the immediately turn around and come back, we should hitch a ride with her family. Plus, my first ever hitchhiking trip was to Florida. 

Before I ever went by Nemo and this site was even born, my inaugural hitchhiking adventure, over freshman winter break, was to The Sunshine State. A friend in my calculus class was from Orlando, and she agreed to give me a ride down there. The plan was to go to Universal Studios Islands of Adventure and see The Wizard World of Harry Potter that had just opened up and then hitchhike home. The amusement park was nice, but the real reason for the trip was to give thumbing it a try. I had backpacked through Europe for seven weeks, that summer, but I eurorailed the whole thing. I wanted to try hitchhiking out on my own turf, in the US, before I did so while adventuring abroad.

Oh, how organized I was back in those days. I had a CouchSurfer lined up for my two nights in Orlando, a lovely working class Moroccan couple, and a place to stay for my night on the road in Jacksonville, a programmer in a swanky downtown apartment. There is so much of the world left to see, so spending my time revisiting central Florida was not a high priority. 

The Adventure:

The Fridays school let out for Spring Break, Savannah, August, and I drove down to Beaufort, SC, home of Paris Island and not much else. Savannah and I spent Saturday afternoon wandering the salt marshes, where we happened upon a nude photo shoot taking place atop the pluff mud for a "school project"...

On Sunday, we left bright and early for Miami. They drove two cars, one their mother was going to take back on Wednesday, one August was going to drive back to Clemson from Tampa the next Sunday. We made great time, stopped for lunch at a Pollo Tropical, the most wonderful Cuban fast food chain, then Savannah and I were dropped off on the side of Highway 1, at the end of I-95, by three in the afternoon. 

Once sunscreen was thoroughly applied, Savannah and I started walking by the side of the road, in search of a good hitch spot. Before we could even find one though, we had a ride. An early nineties, maroon Honda Accord had doubled back to offer us a ride. The driver of the jalopy was René, a delightfully excitable 64 year old Bolivian american who just got off work as a security guard. 

On my trip to The Grand Canyon, with Cayla, we had jokingly tried to get some our drivers to drop everything and go with us on our adventure. It wasn't until our last ride though, on the outskirts of Flagstaff, that someone finally took us up on our offer. This trip though, the first ride bit!

René was heading only about a half hour down the road, but he was so filled with the contagion that was our sense of adventure and spontaneity that he decided to go with us all the way to Key West. After a quick pit stop at his one room/converted one car garage apartment, we had 120 miles to go until Key West. 

driving to key west
Driving Rene's Car
At the 90 miles mark, René had me take over the wheel. This was actually a nice reprieve. I could watch the road and enjoy the gorgeous sunset and not have to keep engaged in the never ceasing conversation that was taking place. Savannah enjoyed it though, she got to speak Spanish for most of the ride.

We went to The Hogfish Bar and Grill, a thatched roof water front bungalow just off of Key West for dinner. As usual, I told the waitress to, "Do me a huge favor and just surprise me." She gave us a free bowl of conch chowder for my "sense of  adventure," which seems a bit mundane when you consider the fact that I basically hitchhiked to the establishment.  

From there we parted with René. We had him drop us off in front of the Key West Botanical Gardens. The gate was easy to go under, and we found a gorgeous spot in front of an inlet to camp for the night. In the morning, we walked into the heart of Key West.

The first half of The Conch Republic is your quintessential strip mall America: McDonalds, big box store, Burger King, big box store, strip mall, strip mall, strip mall. Once you get into the heart of the city, they put a better coat of lacquer on it, but the amount the city has sold out shines through. Nearly all of Duval Street has either become an over priced gift shop selling provocative and/or lewd t-shirt and petty knickknacks or a disingenuous dive bar.  The public's access to the water front has been marginalized to a pay to enter state park and man-made beaches over run with high priced chair rentals and sun bathing guidos and guidettes. All other shore and water access is either for ship docks (understandable) or private resorts (go fly a kite). 

There were a few reprieves though. Sandy's, a walk up diner that also doubles as the office for a laundromat, was in the Cuban neighborhood and rather amazing. And just down the road was El Siboney, another great Cuban joint. Thirty years ago to the day, my father was in Key West for the first time, and juxtapose those stories with mine and the spirit of The Conch Republic is dying. It may live on, a few blocks off of Duval until you hit the bridge to the other half of the island, but the cancer of commercialization is spreading. 

A few objective symptoms of this prognosis, the status of camping: nonexistent on the island. You have to go all the way to Long Key and even then it isn't cheap. Hitchhiking in the entirety of the county, including all of the lower keys up to Marathon: illegal. My fellow peers, some of whom I even noticed were from Clemson may enjoy themselves in the modern Key West, but the swashbuckler spirit that made that city is now just a ghost, a fading apparition of its past self.

how to hitchhike
"Don't judge me because I have a juicy face." 
While trying to find a place to eat our lunch of fresh mango and pineapple, Savannah and I got kicked
out of a private resort and ended up stumbling upon a local artist named Kate. She had a small workshop near The Southernmost Point, and Kate agreed to let us crash their that evening. We napped in the graveyard for the rest of the afternoon and had to sneak out under the front gate because we stayed past close. Before heading back for bed, we tried to find some key lime pie. At $5 a slice or $30 a pie, you better save your pennies if you want a bite of the tart treat in Key West.

When we got back to Kate's, she had already finished off an entire 6-Pack of Heineken, as she sat painting coconuts. We offered her some of our hard cider, and for the next two hours, Savannah and I drank, biding our time with Crayolas and colored pencils, waiting for Kate to call it a night. Her husband came in at one point and wan't happy with us "hippies" being there. As Kate finished up, latter on, he all but kicked us out. So there went our place to sleep.

Our options were walk two hours back to the botanical garden or sneak back into the graveyard. With feet sore from traversing the island twice over that day, we opted for the latter. As we approached the cemetery though, I noticed a house that was under construction. It was completely gutted, so we opted to crash back behind it instead. While setting up, the neighbor's dog started to growl and bark at us. All we wanted to do, at this point, was go to bed, and that mutt forced us to set up camp at a snail's pace, as we tried to avoid making him howl.

Finally, we were in bed, the dog had shut up, and were off to sleep... Until I awoke to Savannah saying, "Everett, wake up! There's a man standing there." And sure enough, there was a creeper hovering over us. Just staring  down at us. As I sat up, he turned and started to briskly walk away. I said something along the lines of, "Hey, sir, please come back here and talk."

More than likely it was just some drunkard who was looking for a place to pee (I mean, it was Saint Patrick's Day), so I just rolled over and went back to bed. Savannah, on the other hand, was a bit wigged out. Atop that, a few hours later, a rain cloud rolled through.

Savannah had set up the camping tarp, and due to the dog next store, I never double checked it. Once the rain started, I pulled the tarp over us, but it was folded length ways, not width ways. We were laying on the 12 foot side and trying to fold the 9 foot side over top of us. I was in the fold of the tarp and didn't really notice the mistake. Savannah, being on the outside did though. In the morning, I was dry and well rested; Savannah was sleep deprived and soaked.
how to hitchhike
Pedro Alverez XXX: The blindfolded voodoo doll I found noosed in a tree via fishing line, at the graveyard. 
We spent most of the next day at the Fort Zachary Taylor State Park (swimming and drying out Savannah's stuff), and in the evening, we walked back to the botanical gardens. Again, we had a great night's sleep there, under the stars. In the morning, we started hitchhiking bright and early. We had a wonderful spot, right after the bridge leaving Key West with a large pull over spot right before the speed limit increased to highway speeds. Within fifteen minutes though, a Monroe County Sheriff pulled over,
"Please, don't tell me you're hitchhiking."
[Well that's not a loaded question.]"... Well, I wouldn't want to lie to you, officer."
"Would you like to continue hitchhiking."
"Preferably, yes."
"Well I can give you a ride. A ride to jail."
[What a dick.]"... ah"
And with that, Key West flat lined in my heart. Key West is dead.

Thankfully, public transit was (surprisingly) there to save us from Officer Douchebag. The bus to the county line is $4 regular/$2 reduced fair. And from Marathon, there is a bus all the way to the mainland, Florida City, for only $2.65. With help from the local homeless population, we scrounged up the 30 cents needed to make exact change.

Pro Tip: If a homeless guy on a bench asks you if you're 21. You're not. He'll want you to buy him a liter of really bad vodka because the lady who runs the local liquor store refuses to serve him.

The ride up to Florida City took about two hours. It dropped us of at the local Walmart, and from there, we walked to a hitch spot twenty minutes away. Literally, as soon as I stuck my thumb out, we had a ride with Nando and his five year old son. They were headed to a birthday party, and it turns out, we were heading the wrong direction. I had flubbed on my navigation, and we were headed west instead of north.

Luckily, Nando only took us a few miles down the road, and he was heading north after the birthday party. Just those few miles though put us in a completely different world. Instead of suburbia and Walmart, we were now surrounded by gorgeous farmland. The air was fresher. The road north was a lot less busy, but hell, it was a nicer place to stand and hitchhike.

Within a half hour, we were picked up by a lunch truck that doubled back for us. He had to make one last stop for the day, but after that he brought us north and a bit back east, to the main road. Interestingly, our ride escaped from Cuba at 17. His father was a political prisoner there for 26 years, and his son is studying Computer Engineering at Columbia University and won both the quarter million and full million dollar grants from the Bill and Malinda Gates Foundation.

Our final ride of the day was with a mechanic at the local nuclear power plant who'd immigrated from Ecuador. He had just gotten off a 12 hour shift. Once ever year and a half, they change the uranium fuel core in the reactor, and for that entire month the staff has to work twelve hour days, six days a week. Essentially, you're either at work or asleep for the entire month, but hey, the pay is great.

Even after finishing such a long shift, he was kind enough to bring us fifteen minutes out of his way, up to Tamiami Trail, our route through The Everglades. At that intersection there was a gas station and this seemingly random casino. We'd been driving through farmland for the past half hour and then all of the sudden, at the edge of The Everglades, there was this large, flashy gambling hall and hotel.
how to hitchhike
Miccosukee Bingo & Gaming: Towards the center of the image you can see the open air hut we tried to sleep in.
Savannah and I left our bags in a small hut on the outskirts of the casino's parking lot that looked rather unused. Once inside, we found a comfy couch to loiter on and with an outlet nearby to charge up our electronics. Recharged, we returned to our hut to eat dinner, and while trying to enjoy our pita, hummus, and tuna sandwiches, we were assaulted by mosquitoes.

Being the proactive sort, Savannah went to the gas station to fetch some bug spray, while I set up our bedding. Once she returned, we dowsed ourselves in deet, but the bugs still bit. We put on our long sleeves, but the bugs still bit. It was too hot to be in our sleeping bags, but even through the our liners (cotton and silk), the bugs still bit. Finally, around 2 am we had had enough. And I decided to go the casino to try and find a place to squat.

Unlike squatting at a five star hotel, a casino is an extremely hard place to crash. Most normal employees don't want to be intrusive to possible patrons, but for security guards, that's their job. And a casino has a lot of security guards and many, many more cameras. This helps to prevent theft and schemers, but it also makes squatting near impossible, especially for two people. Honestly, the only way I think you can crash in a casino like Miccosukee, that has a no sleeping policy, is to zonk out in front of a slot machine. With that said, Savannah and I played cat and mouse with the casino security for three hours, trying to find a place to get some shut eye to no avail.

how to hitchhike
Open air beehive outside the casino
By five in the morning, we just conceded to wandering the casino, after we could tell higher and higher levels of management were coming by to make sure that we were awake. At six, we ate at their all you can eat buffet, filled Savannah's backpack with fruit and granola, and by that point, finally, the sun was up. We returned to our hut, and with the mosquitoes gone, we got some much needed rest. From sometime before seven to sometime just before noon, she and I slept like boulders.

Finally rested, we got back on the road. Tamiami Trail cuts through the heart of The Everglades, and our hope was to be able to enjoy the sites as we drove through (and avoid the mosquitoes). We managed to avoid the flying blood suckers, but both Savannah and I were unable to appreciate the drive through. After a half hour in the baking sun, waiting for a ride, a red pickup pulled over, helmed by Ace.

Ace is a "treasure hunter" from Missouri who's been living in The Keys for the past two decades. He's moving back to his home state because the progressives/communists/devils, won't let him dig up "his treasure". Apparently, the government wrongly places a higher value on those coral reef things than  gold bars that look like every other gold bar but sunk with some ship a few hundred years ago. Savannah, a studding conversation biologist, was too nice to say anything, but I could tell that she was fuming.

From his line about the progressives/communists/devils, he then proceeded into a rant about far right-wing politics. Ace doesn't have a television, but somehow only Fox News can be trusted and Glenn Beck is even better. Oh, and something about Benghazi and FEMA camps, Obama only supports Muslims, and somehow Putin is awesome (even though he was part of the Communist Party of the Soviet Union until it dissolved...).

Pretty soon into the ride, Savannah wanted out, but I tried to reassure her that I could handle the situation. Even my best attempts to keep the conversation on neutral, amicable subjects was thwarted though. The longest reprieve was when I got him talking about his life's work. For the past twenty-eight years, Ace has been working on finding treasure in Missouri. This "treasure" was, according to Ace, hidden by the Native Americans, who stole gold from the US government, toted it around the plains for a while, and then decided to bury it so no one could find it (except that they left National Treasure-esq clues all around in stone carvings so you could find it, if you really tried).
How to Hitchhike
Even after 28 year, Ace is still trying to become Nicolas Cage
This is all coming from a man driving a truck with 420,000 miles on it. Who, with this scheme, is apparently trying to out smart a billionaire from becoming a multi-billionaire. Yet, he asked us to envision a trillion dollars and couldn't understand my response of 10^12, after only a brief moment's pause, doesn't comprehend the gold standard/lack there of, but he was on point, at least, about Christopher Columbus.

After all of this, I was ready to get out too. He was going all the way up to Mile 129, but at about Mile 99 there was a gas station and a sign for Interstate 75. Savannah jumped on the opportunity saying, "Oh, that's our stop!" Even though we were only two-thirds the way through The Everglades.

Sort of dazed from our hour in the car with Ace, we ate lunch, before continuing to hitchhike Tamiami. If it were only me, I probably would have stuck it out with Ace, but still, I was not at all upset that Savannah had him let us out when he did. Trying to keep the Crazy Train on the tracks is exhausting work.

Being on the road and traveling adds a lot of perspective on life and how quickly the lows, like Ace, can become highs, like our next ride. After only a few minutes, a shiny, red Cadillac passed us by. Savannah remarked, "That girl reminds me of my little sister." And sure enough, the Caddy pulled over. A mom and her two daughters (who were using the grandparent's car), picked us up.

The elder daughter, Meghan, oddly enough is a graduate student at Indiana University, where I hitchhiked up to last Spring Break. She has traveled quite a bit herself, is studding public policy for environmental issues, and in just about every regard, is the antithesis of Ace. Or to put it simply, she's awesome! After dropping us of at the foot of I-75, in Naples, Savannah and I were just enamored with, especially juxtapose to our previous ride, how wonderful Meghan, her sister, and her mother had been.

Our final ride for the day was another great ride, with Max. While waiting for it though, we started to get boxed in with vehicles that were pulling over but not for us. First a sedan and a motorcycle stopped on the shoulder and the drivers started chatting. A few minutes later a Cadillac Escalade pulled up right in front of us, only to have the passenger put her head out the window and puke her guts out. Somehow, in all that craziness, Max saw us, pulled over, and gave us a ride in his mud splattered Jeep Wrangler.

Max is of Dominican decent, and like me, is a racial quagmire for most. He did two tours over seas in the Army's 101st Airborne, currently works as a mechanic, and was headed back from work, to see his wife and four year old daughter. It's always interesting meeting people who push your expectations, even in the subtlest dimensions. Max was in no way fits the confines of the ex-military stereotype that most service men, past and present, who pick me up tend to fall so squarely into.

The spot, he dropped us off at couldn't have been better. It was an area in the midst of becoming an open air shopping center with apartments around it, so there was food and shops but not still a vacant, undeveloped lot to sleep in. Knowing this was probably going to be our last night on the road, we ate a celebratory dinner, got candy at the Target for desert, and then went to sleep behind a tree and some shrubs in the vacant lot.

How to Hitchhike
Free food for everyone!
In the morning, we crashed the continental breakfast at the Holiday Inn Express next door, before hitting the road. Savannah almost got us thrown out though, when she asked one of the workers what time breakfast ended, as they were packing everything up. Once well fed, we walked to the on-ramp to the interstate. The ramp was bifurcated, meaning that their is an on-ramp for both directions of traffic. Generally, you want to hitch the one that does not make a large swooping turn because it is dangerous and hard for drivers to pull over.

Thus, to start out, we were position before the straight ramp, but the traffic from the other direction was much busier. After a half-hour of skunk luck, I decided to go and scope out the other on-ramp to see if the it was hitchable. I left Savannah hitchhing on the other side of the road, just in case, and by the time I got back, a minute later, she had snagged us a ride.

The minivan said "TAXI" on the side, so I double checked with the driver, JC, before climbing in that this was a toll free ride and that he was indeed headed north, and we were off. I did not vet him enough though. Savannah had not asked two crucial follow up questions (and I failed make sure), "About far up the road is that?" and "Is that busier than here?"

JC took us from our el primo, super busy spot five miles down the road to a somewhat trafficked/just a step above desolate intersection. If a ride isn't going more than 15-20 minutes down the road or to a busier interchange, don't take the ride! But Savannah didn't know that, so we were relocated five miles closer to Saint Petersburg but set in Nowhereland.

how to hitchhike
What I had waiting for me in St. Pete
After an hour of reading and my girlfriend getting passive aggressive about the fact that I wasn't thrilled with the current situation, we were picked up by Bob. Unlike Max, Bob was very clearly of military stock. He'd served in the Navy, and was putting his newly purchased cans of beer in the back seat when I ran up to the car. One of them was open, but I seemed completely sober. It took a while to figure out why Bob was driving up from Fort Myers, though. At first he used the vague descriptor of "stuff", which I figured was drugs. It turns out it was just guns, though.

Bob let us out on the interstate, at the turn off for I-275, and we walked a mile to the nearest and only exit before the Skyway Bridge. The Skyway is amazing. It cuts across the mouth of Tampa Bay, but for some reason they didn't build a bike or walking path along it. So we had to hitchhike the last few miles, even though I would have enjoyed walking it.

It took about another hour long wait for Gustavo to pick us up. Gustavo was a journeyman welder on the way home for the weekend, and he was nice enough to drop us of right at Savannah's grandparent's doorstep, in St. Pete. For the two days we ate, drank, slept on her grandparent's back patio, and I discovered Kakuro/cross sums, before we drove with her brother, August, back up to Clemson.

If you're looking to learn how to hitchhike, check out my book- The Hitchhiker's Guide to: Earth.

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Location: Key West, FL 33040, USA


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