The hitchhiker's guide to Florida

Pirates, savages, Capri-Sun – how to hitchhike Florida and survive

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He thinks for a minute and adds, "Or it's the people who are bored."

That seems to fit David and Britney; they decide to take us an extra 20 miles ("We have nothing else to do," David says).

They drop off us at the intersection of U.S. 301 and State Road 100, which will lead us straight to the east coast. Almost immediately, a Brooklynite named Jensen gives us a lift. Returning to Jacksonville after a construction job in Gainesville, Jensen ran out of gas a few miles back and had to pawn his tools for the gas money home.

"You can rob me if you want," he says, looking back at me. "But I got no money. It wouldn't bother me, though, if you did."

Jensen drives as I imagine Neal Cassady must have: swerving maniacally, yet fully in control. He's going at least 30 miles over the speed limit, and he always seems to be looking at us, not the road.

Jensen talks rapidly about the million dollars he earned through investments in his early 20s and how he squandered it all on cars and cocaine. He's an animal lover but vaguely racist. When we pass a black hitchhiker, he smiles: "Sorry, brother."

He takes us only 20 miles and promises to come back for us, but after he speeds off, our thumbs attract another kind driver.

Amy, a single mom and community college student, pulls her blue Chevy truck over and motions for us to hop in the back. She's going right into Daytona Beach for a ride with an ambulance ("It's for school," she says). Once we're settled in, she hands us two Capri-Suns.

An hour later, we reach the beach and run toward the Atlantic Ocean in our boxers. It's our first bath in two days. But our celebration soon ends. Rain clouds from the west move in quickly and within the hour we're under a Kangaroo gas station awning while the skies pour their fury on us. This isn't going to be an easy night. Where are we going to sleep?

That's when we meet the Pirate.

Dressed in a pair of tattered shorts, his stringy blonde hair poking out of a bandanna, John definitely looks the part of a pirate. Faced with no other choice, we take him up on his offer of a motel. At least until the rain stops.

"I got into some money lately and I'm visitin' my daughter this week," he begins in a thick Rhode Island accent. "I do that three or fo' times a yea'. I got two guys f'om the pawk stayin' wit me already and some girls are supposed to come by, but you can hang out as long as you want."

I'm a little suspicious; Ethan is giddy.

"I love being adopted," he says.

Inside, the Pirate introduces us to the Irishman, a homeless Vietnam vet of Irish descent, and the Caveman, so named because the unkempt black beard that covers most of his face reminds the Pirate of a certain Geico commercial.

The Pirate found his two vagrant friends after work one day and offered them a place to stay out of the rain. He was supposed to return with girls and rum, his new friends admonish him. But instead, he's brought back two stinky hitchhikers.

click to enlarge REDNECK COUNTRY: A few of the items sold at the Waldo Flea Market. - ALEX PICKETT
Alex Pickett
REDNECK COUNTRY: A few of the items sold at the Waldo Flea Market.

While the three men pass a bottle of whiskey, Ethan shares his cross-country adventures. The Pirate and the Caveman think he's crazy for hitchhiking, but the Irishman understands. The vet tells us he's been to every state and over 20 countries. He urges Ethan to continue his travels.

One by one, the men pass out. Ethan and I decide to crash on their floor. Tonight, we'll stay dry.

The next morning, Ethan and I bid farewell to our new friends and spend the morning on the beach. By noon, we walk seven miles to the I-4 on ramp, confident we'll make it to Tampa before nightfall.

Hitchhiking rule No. 2: Nothing is guaranteed.

We leave Daytona Beach with a couple on their way to the Orlando airport. But much to our chagrin, they decide to drop us off in the suburban hell of Altamonte Springs. All the buildings look the same. So do the cars. And everyone stares at us like they've never seen hitchhikers.

Within 15 minutes, two Altamonte Springs police officers yell at us from their patrol cars to get off the on-ramp. As we walk down the road, four more police cars pass us slowly.

I secure us a ride at a gas station with a man heading just two exits up to a more desolate, wooded area right outside Orlando, but there our bad luck continues for two hours. My thumb actually starts to cramp. Seven different cars give us the mocking thumbs-up. I hate Orlando.

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