Chillest Tour Ever: Florida, Day Three

To the residents of Chokoloskee, our waking up at sunrise looks like two kids sleeping in. Well before first light, the sound of golf carts and RV propane hookups break us from that kind of comatose sleep you only get on bike tour, leaving us to slowly consider actually waking up for another hour or so.

The night before I talked with a resident of the island. He saw me taking pictures of this and that, and was curious what I thought of the place. In a baseball cap and faded shirt that had something about loving fishing written on it, I assumed he was angling for some compliments. Truth be told, my only experience with the island so far had been biking to this rv park and watching the sunset. But, I told him how it felt like everyone really loved being here. He liked that. "Just wait another forty years and you could be down here too," he said. And honestly, I didn't really know what he meant by that. Did I miss a sign coming in that said "Must be 65 or older to live here" or was he making assumptions on the dirtbag bike tourist lifestyle we presented?

About three hundred and fifty people live on the tiny island, and as we exited the park I noticed a bulletin board with three "for sale" flyers on it. One was for a trailer lot. Another, for a boat. The last one was for a golf cart. All three formatted identically, clearly authored by the same person. That's when it dawned on me: that man was implying it would be 40 years before enough of the island's residents had "moved on" for there to be room for me.

The man walked out to the dock, climbed into his boat, and motored away- leaving me trapped in existential dread.

You'll see signs all over the island directing you to it, but the Smallwood Store at the southern tip of Chokoloskee- that is, the southern tip of gulf coastal Florida, is very important to the pioneer history of the state. By extension, its important to the history of much of the mid-1800s east coast and the Florida Keys. Southern Florida in the 1840's was a wild place. Decades of war with the area's indigenous population, as the "ownership" of the land transferred between various european countries and, finally, the United States, had left areas for whites to homestead without the risks inherent in westward expansion. The delicate relationship between the land and water made certain mangrove islands incredibly fertile, with a growing season unheard of anywhere else in America.

The Smallwood Store was the hub for southern Floridian agriculture. All of Chokoloskee Island's land, though now occupied predominantly by trailers, was being farmed by a couple of families. The growing conditions were so prosperous that this island, combined with a few others that have since returned to protected mangrove sanctuaries, grew much of the east coast's winter produce. The Smallwood Store, if not selling directly, served as a port to load produce for ships headed north via the Gulf of Mexico, or to be transferred to steamships along the Atlantic Coast's shipping routes and down to Key West. Had places like California not become options for year-round growing, without the chaotic storm dangers of southern Florida, this island might still be one filled with crops instead of silver-haired retirees.

This is just part of Chokoloskee's story. Murders, outlaw hideouts, the growth and prosperity of the Calusa's society and later the Seminole, as well as runaway enslaved people's stories are all part of this tiny island's history. We headed back north to Everglades City for a visit at the Everglades National Park Gulf Coast Visitor Center to learn even more about these ten thousand islands.

Yeah, We Took A Boat Tour.

It's super basic and touristy, but it's with great shame that I admit we didn't have the time or means to venture out on our own in kayaks and thus took a boat tour with a group of grandmas. This tour would specialize in the mangroves that make up the ten thousand islands and much of the coastal everglades. We left Everglades City, motoring into Chokoloskee Bay. Our guide, our captain, Joyce, in her thick Boston accent said we'd be going up the Turner River.

Vultures hang in the trees- we even catch glimpses of dolphins coming up for air, though I don't get any usable photos of them. The water is only a few feet deep in Chokoloskee Bay. You could stand in most parts and confidently not drown. The mouth of the turner river brings us into a dark, muddy world. Mangroves thrive here, and serve as the foundation for an entire ecosystem.

The canopy closes up above us. There's a steady wind from upriver, and the heat from the bay dissipates here in the shade. The Red Mangrove's slender roots dip into the black water, some dangling above to take advantage of the nutrients that swim along the surface during high tide. This kind of specialization is how the mangroves survive in the brackish water. Snowy Egrets fly overhead, landing on branches in the distance. It's like they're playing a game, flying just far enough ahead and waiting for us to catch up before flying away again. It's infuriating trying to take their picture, but just watching their graceful flight is cool enough.

Red Mangrove Propagule

So, it's not really a seed, per se. The red mangrove species maintains an embryonic cell, kinda like how mammals do in their bellies, but this one grows on the tree for the first part of its life. Only once it reaches a point of maturation will it seperate and fall into the water below. Captain Joyce lets us pull one out of the water to inspect. They bob just like a fishing lure, the long green extension from the upper pod keeps the propagule vertical in the water. This lets 'em float around until they're ready to dig into some sweet, sweet mud and grow into a whole crazy mangrove tree.

Fun Fact: This has absolutely nothing to do with bike touring, it's just really cool.


There's all kinds of critters in these mangroves, not just paparazzi-plagued alligators in these tour boats. Above and below the water, little creepy crawlies make their home amongst the mangroves. One of the most camera shy are the mangrove tree crabs. They're tiny, camouflaged against the bark they crawl along, and fast. They tend to see us well before we see them, but Captain Joyce has a trained eye and a practiced grab- enough so to nab one off a branch and bring on board for us to admire. They don't like being held (crazy, I know) but we take turns clapping our palms around the probably-terrified crustacean until it finally jumps overboard.

We pass long-distance canoers enjoying the Wilderness Waterway, a 99-mile canoe trail through southwestern florida. Im immediately envious of their freedom Im denied myself by being on this scheduled boat tour. Nothing against the tour though, I've learned a lot and got to hold a little pissed-off crab after all. Im also jealous of how much room their self-powered vessels have for storage compared to a bicycle. I haven't forgotten this is a story about a bike tour, by the way, but if you go to the Everglades and never get in a boat then you've wasted your time.

An osprey roosts on a sign
asking folks to take caution
for the manatees.

Florida, am I right?

Okay, fine, back to riding bikes. Our boat docks and we thank Captain Joyce endlessly for her knowledge and her Bostonian sense of humor. Jana hooks Joyce up with a tip and we find our bikes just where we left them. It's noon, and all that's left is for us to make the easy thirty mile ride to Marco Island- our last destination here on the Gulf Coast.


Heading north there's just enough wind to be annoying. Not frustrating, just annoying like that one uncle who is always kinda making fun of you but in a joking way. Either way, you gotta put up with it and if you say anything about it suddenly you're the asshole and- sorry. Anyway, that's how this wind is.

But back on the Tamiami Trail, there's no thanksgiving-uncle-wind, just the great no-association-tailwind we've come to know and love riding our bikes westward across Florida. We're even treated to every cyclist's favorite power dynamic flip: riding past dozens of upset cars stuck in a traffic jam.


The lane-hogging, horrible facial expressions, and general glee of having the road to ourselves is short-lived as the wall of traffic is unleashed. Everyone speeds by, and around the same time the shoulder is suddenly plagued by rumble strips. It goes on like this for five miles, and we alternate between trying to ride closest to the guard rail on busted up pavement, panniers a few inches from the rail, or threading the needle and getting our tires between the white blocks of the strips. Both options suck, but the latter is slightly less of a pain. When the road is clear of cars, we slide over into the traffic lane, looking over our shoulders every five seconds to see if anything is coming up behind us. This is the hardest part of the bike tour so far, but it's just a five mile chunk of poorly-maintained highway, so in that context it ain't so bad.

We leave the Tamiami Trail for the final time, heading south again over the Goodland Bay. The bridge is the only climbing we've done since leaving Miami, and from it we can mangroves far and wide. In the distance, there are tall buildings. Doing absolutely zero research ahead of time, we just assume that's Marco Island without really knowing what to expect.

Here's what happened: last night we stayed on a tiny, little island on the coast of Florida that was not insanely developed in the name of Florida's tourism industry. This experience left us with the naive that, hey, maybe other spots on gulf side would be the same. Maybe you only get into the craziness of ocean-side Miami (our only experience to measure vacation-destination-Florida by) like up by Tampa, and Marco Island will be another, little treasure of a town.

We were wrong. By the first traffic light (and by the way it's really nice realizing you totally forgot about traffic lights) we see that every single corner of Marco Island is developed. We figured we'd find a place to stealthcamp for the night. Nah. A trip to the local bike shop for info was pointless, but we could rent beach cruisers. With no open space, the only stealth camping possibilities would be back in the mangroves, with the alligators and a respectable number of mosquitos. The manager directs us to a nearby church, whose pastor is an avid cyclist, but their office is closed for the day. Usually the lack of planning isn't an issue, but this place is just enough crowded with family vacationers and retiree residents that setting up in a church courtyard without permission smells suspiciously like a trespassing charge. Disappointed that our usual tactic of just showing up somewhere and finding cheap/free camping, we tuck our tails and find the cheapest motel in town.

I won't bother to say how expensive it was. Feel free to look up Marco Island motels is you want to know, but it basically doubled our expenses for this whole trip. Now, you might think that being stuck in this land of hotels and condos we'd be miserable, but Marco Island has a few redeeming qualities to it. What could it possibly have? Well, friggin' burrowing owls for one.

That's right: Owls. Burrowing owls. Little burrowing owls. Despite the island's building boom, these owls were here first, and the island is so respectful of this that wherever they choose to burrow immediately becomes a protected spot, and residents must obtain a permit to destroy the burrow. Judging by the frequency in which we saw their burrows fenced off, with conservation signage, it seemed like Marco Island's residents are chill with the owls. We're checking out the owls on our way to another charming oasis here: Tigertail Beach. Our new friends we met while visiting Chokoloskee gave us the low down on this spot, and given the impending sunset we had to literally sprint to make it there on time.

Jana, hulking out, once again was channeling such ultra energy that her new identity finally revealed itself.

Introducing Cycling's Non-Ironic Long Walk On The Beach: Ultra Slowmance

After three days of narrow highway shoulder, camping along dirt roads, and hiking through swampland, she reached the gulf coast and completed her metamorphosis into a true pioneer in #basketpacking, #snackpacking, and #rackpacking- a new method of using bike-mounted racks to hold and stabilize extra-large bikepacking bags.

She wears lots of clothes. She wears lots of sunscreen. But she thinks skids are pointless, so she doesn't wear down tires.

But we didn't sprint all this way for an elaborate joke making fun of current trends in the hipster cycling world. Tigertail beach sits across a tidal lagoon from Sand Dollar Island. Sand Dollar Island is quite remote, and an oasis for migratory birds. The only way to it? Walk across the lagoon, of course.

Sunset over the Gulf of Mexico

Pretty okay lookin'

And then it's back to the land of condos. Our motel room has three seperate beds in it for some reason, but we each find one to pass out in. I can hear a slight drizzle outside, a storm must have blown in from the gulf.

Route Map

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