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Mission Wet and Wild

What happened when a city slicker kayaked into the Everglades on an overnight adventure.

Photography by Jim Freeman

Ahh, camping. Perhaps you’ve heard of it. As a bon vivant, my association with camping falls somewhere between “what’s a tent?” and “uh, no.” But there is a reason we all moved to Southwest Florida: It’s absolutely beautiful here

The weather. The water. The landscape.

It begs to be explored. But the sad truth is that most of us don’t venture past the parking lots—a quick stop at Waterside Shops before enjoying cocktails at LaPlaya. If we’re lucky, we might take in a beach day once in a great while or hit the links of TiburÓn. But if that is your reality—and let’s face it, it’s most of our realities—you owe it to yourself to explore the true beauty of this area: a world without pavement, parking meters or golf carts.

And nothing screams both “adventure” and “Southwest Florida” like the Everglades.

So we called Cynthia Gilbert at Kayak SW Florida and booked an overnight kayaking expedition in Everglades National Park departing from Everglades City. The park is one-and-a half million acres of wet, while Everglades City is the last bastion of civilization on the edge of one of the world’s largest mangrove forests. (So as not to completely shock the system, Everglades City is also home to some cute little restaurants.)

A visit to her website, kayakswflorida.com, listed multiple trips and outings that I could join. My first choice, a ladies-only, vegan, three-day full-moon trip, proved to be too complicated and late in the month for my purposes. Not to mention it would have also been awkward due to my Y chromosome and hamburger fetish. But there was also a two-day, one-night kayaking/ camping trip posted that was the perfect opportunity for a city slicker like me to get his feet wet. Literally. (Never mind the fact that the only tents I’ve ever been in were at New York’s Fashion Week, and roughing it implied room service that stopped serving at 11 p.m.)

“Depending on your level of fitness and experience, we can travel as near or as far as you like,” said Gilbert, a 46-year-old former derivatives/ foreign exchange broker from Chicago turned kayak entrepreneur. “There’s a shady spot for the tent on Rabbit Key ... Have you read Killing Mr. Watson? He was buried there temporarily after the townspeople of Chokoloskee shot him dead.”

So, let me get this straight: I’m heading into the wilderness with a group of people I’ve never met? Well, by all means, let’s head out to a spot that’s convenient for body disposal. As Bear Grylls says, “If you risk nothing, you gain nothing.” (Plus, there was still a shot I’d have cell service.)

Ironically, what’s most appealing about the trips through Kayak SW Florida is that they are, for the most part, bare bones packages. Although they can get you the requisite paraphernalia (kayaks, tents and other stuff ), they don’t cook your meals, set up your equipment or provide any musical entertainment—they’re just professional guides who’ll keep you from never being heard from again.


Is it wet?: There's a reason people go places in Range Rovers--packing and unpacking kayaks can be a challenge.

Getting in isn't much easier.

Gilbert, a Florida Master Naturalist Guide, knows these islands and waterways like the back of her hand, and I can promise you that without a guide, you’re in real danger. Almost everything looks alike out there and what few landmarks you might find are merely temporary thanks to the tide.

Nevertheless, talking to her before the trip was an energizing (and sobering) exercise in adult learning. First, if you plan an overnight kayaking trip (she also offers day trips), don’t expect to paddle up to The Ritz-Carlton. You’ll tent it, thank you very much. And, as the word kayak might imply, you’re paddling that 17-foot floating sliver yourself all the way to your destination. That’s a minimum of five miles and, if you’re the hearty type, can be as far away as the Keys (that’s far). Our destination? Jewel Key. A beautiful barrier island just five miles from our spot of departure, the Ranger station in Everglades City. (Apparently, Cynthia was not convinced we could make it the 12 miles to Rabbit Key—even though a dead man once made it there and back.)

Our group of four (Cynthia; myself; photographer Jim Freeman; and Steve Riley, a 49-year-old from Atlanta who just wrapped up a two-day stint at a Sarasota Buddhist retreat) met at Island Café in town at 8:30 a.m. on a Monday morning to introduce ourselves, discuss what’s in store for us and, in my case, enjoy some more-than-adequate French toast.

Before long, we were headed for the canoe launch at the Ranger’s station to fill out the proper paperwork (you need a permit to camp on the islands or you will find yourself voted off just like Survivor). Gilbert was nice enough to provide each of us with the proper equipment, including the kayaks (fiberglass Nigel Dennis kayaks imported from Wales and costing between $4,000-$5,000 each), new tents from REI, sleeping bags and more. She probably assumed it was better to be safe than sorry when I informed her I could bring little more than food, water, sunscreen, champagne and aspirin.

And while the day was windy and included a small-craft advisory (wait, what?), the most challenging part of the experience was packing the kayaks. These gorgeous sea-going vessels featured three storage compartments accessible via 10-inch and eight-inch holes up top.

Nothing any of us packed fit into holes of that size, so we had to repack in watertight compression bags Gilbert brought (because this was not her first time dealing with newbies). We then had to forcibly cram these bags into these cubbyholes, basically destroying the gourmet edibles I had brought along—namely Life cereal and a carrot cake from Publix. (Hey, a boy has got to eat.)

Which way to The Ritz? Exploring the 10,000 Islands with a guide is a rewarding and Zen-like way to recharge your batteries.

An hour later, it was time to shove off on the adventure of a lifetime (or a Monday into Tuesday). Of course, none of us were kayakers, so just getting into the things required walking into knee-deep water and having Cynthia sit on the front of the kayaks to steady them. I’m proud to say no one fell in. As nondenominational miracles go, that was a biggie. We then pointed our kayaks west, across the vast expanse of the Chokoloskee Bay, and with the sun at our backs, we began the long excursion to the Gulf.

Even with the tide in our favor, paddling the five miles to Jewel Key, across wide open water and through the mangroves that line the Chokoloskee Pass was what the infirm might call “tiring.” Along the way we were tailgated by dolphins, dazzled by flocks of white pelicans, stared at by some osprey and basically ignored by white ibis. We then spotted our destination in the distance: a sun-lit green gem flanked by a seductive belt of sand. It was absolutely stunning. There was also a Port-O-Let rising mightily over the beach—a beacon of hope to those who underestimated their water intake at breakfast.

“How long did that take?” I asked Gilbert.

“Just under two hours,” she said, in a good-natured tone that let me know it was a spectacularly disappointing time for anyone not attached to an anchor.

“How long does it normally take?”

“45 minutes … We should unpack the kayaks.”

It turns out that getting your crushed Life cereal out of a kayak is only marginally easier than getting it in. But if I was going to reach the tent I had packed underneath, that’s exactly what I was going to have to do. And so, after a cursory inspection of the island and its beach it’s a tiny island—we all chose locations for our tents approximately 70 feet apart from each other (because that’s what people do). Steve, who I may have mentioned just returned from a Buddhist retreat in Sarasota, chose not to bring a tent during the difficult packing process, instead, going with a space-saving hammock with wrap-around no-seeum netting. In a flash he was headed into the woods to find two trunks in close proximity.

The rest of us began the shockingly easy task of putting up our tents (new ones almost put themselves together) right on the beach, just above the high tide line (yet within easy walking distance of the aforementioned Port-O-Let).

“I thought we could wrap things up here and kayak over to a very cool area that only appears at low tide,” said Gilbert. “It is like the surface of another planet.”

That was enough to get Steve and me back in our kayaks and fighting a very strong headwind toward destinations unknown. It also gave me a chance to talk to Steve. You learn a lot about people when television isn’t an option. It turns out that Steve’s tech business tanked and he is taking advantage of his newfound free time to explore Florida. He’s also enormously self-reflective.

“That sunset is my religion ... That group of fish jumping is my religion ...” Those were the kind of things that would come out of his mouth. You know, Buddhist stuff .

Low tide is a fascinating time in the 10,000 Islands area of the park. As we were all paddling our way to the magical Briga-dune that only appeared as the waters receded, it became clear that a majority of the one-and-a-half miles of open water we were traversing was only eight inches deep. Hand to God. It would have been faster to just get out and walk. With every stroke of the paddle, it was though we were shoveling sandbags. It was amazing.

But not as amazing as the dune Gilbert brought us to.

“It’s an old oyster bar,” said Gilbert. “Isn’t it cool?”

While a small section of the bar has sand, most of it is made up of encrusted oyster shells.

“Do you hear that?” said Steve. “It’s a clicking. It’s been driving me crazy.”

“I’ve been told by many people that that’s the oysters snapping shut,” said Gilbert.

It was immediately clear that the “snapping shut” was also Steve’s religion.

“There is a whole other world out here when you stop to look at it,” said Gilbert. “You don’t see it when you are going by in your speedboat.”

Awaiting the green flash: Champagne, carrot cake and great conversation bring a little civility to the wildness of a Jewel Key sunset.

After an hour or so of wading through tidal pools and examining some monstrous conch shells, we began the long paddle back to Jewel Key. The wind was picking up by this point, making the small-craft advisory seem reasonable and forcing this kayaker off course, fighting two-foot waves in a boat that freeboards four inches. I wondered if this would be an appropriate time to tell the group I can’t swim. Luckily, I’m only 50 yards from being able to walk the other mile back to camp.

It should be noted that a day on the water, with the bright Florida sunshine hitting you from all angles, can be remarkably tiring. So when we finally returned to the campsite and enjoyed dinner while watching a spectacular sunset fall over the Gulf of Mexico (which included the mystical green flash!), it was fairly surprising to discover it’s only 7:24 p.m.

“Oh my god, back home Wheel of Fortune isn’t even over yet.”

“Nature messes with you,” said Steve.

“What I wouldn’t give to see the glow of a portable screen

And just like that, both Steve and Cynthia pulled out their iPhone and iPads, respectively. Sadly, the cliché campfire I had envisioned from before this adventure began was squashed by the high winds. So we finished off the champagne, the wine and the carrot cake (camping doesn’t necessarily need to be uncivilized) and began identifying constellations with the iPad. Jim, our elder statesman, called it a night.

And so, with no fire, no television and no more champagne, we, too, decided to retire to our polyester and mesh abodes before 10 p.m.

If you’ve never slept in a tent before, alone and in the dark, I can assure you it is nature’s answer to the Miracle Ear. You hear things that aren’t even happening.

Was that scratching? Raccoon!?!? Nope. The wind.

Is that something breathing outside the tent? Nope. That’s me.

By midnight I gave up all interest in whatever was or wasn’t happening outside my tent. I slid the zipper to my sleeping bag up to my nose and called it a night.

That lasted about two hours before a lengthy and violent splashing began in earnest just 30 feet from my door. As someone who’s watched plenty of Animal Planet, I knew the sound of a momma grizzly racing down a streambed on the hunt for salmon. But as I peeked out the mesh, all I could see were millions of stars and glistening water rushing with the tides. Trust me, I looked—hard. But the combination of exhaustion, champagne and a very comfortable sleeping bag convinced me to chalk it up to the ghost of Mr. Watson. Only in the morning did I learn from Gilbert that the noise was a pod of dolphin corralling schools of fish into the narrows near my tent and gorging on sushi. SeaWorld was just feet away! Next time I’m getting up when I hear splashing.

Campsite coalition: Modern tents are surprisingly easy to put together.

But they're still more complicated than a hammock.

There are few things more spiritual than sunrise in the Everglades, and after debating what the Buddhists would think of it, it was time to break down the camp. You would assume that breaking things down would be easier, but by then everything had sand covering it and the plates and silverware were covered in carrot cake residue. Ugh, camping.

We decided to take a different route back to the Ranger’s station to experience secret gardens made of mangrove tunnels and the shell mounds built by the Calusa some 14,000 years ago. (They loved their shellfish.) We planned to hike the island, but the wind and the small craft advisory were still in effect as we stared down the wide-open water of Chokoloskee Bay with a 25 mph headwind. Add an outgoing tide, and the group was actually going more slowly than our blister blistering pace set the day before. We were soaked and certainly going to feel it in our arms the next day.

“Just being out here is my religion.” Amen, Steve. I totally agree. But I think we have to unpack the kayaks again.

Under the guise of Mr. Adventure we’ll be starting a monthly column in January where we’ll explore some of the more interesting facets of Southwest Florida— from the sublime to the excruciating. If you have any topic suggestions for Mr. Adventure, email Michael Korb at mkorb@gulfshorelife.com.



OVERNIGHT TRIPS REQUIRE A TENT OR, depending on if the island you camp at has a clump of high-canopy trees, a protected hammock. (It’s really buggy out there.) To that end, tents and hammocks should feature no-see-um mesh. Along with your tent you should bring at least one tarp for a footprint, stakes, poles and a repair kit (aka duct tape). You’ll also want to consider a Crazy Creek packable chair. Speaking of fitting things in the kayaks, luggage won’t cut it, so bring compression dry bags.

Bring hard plastic or metal water bottles as crows and raccoons can open traditional water bottles. You’ll also want a sleeping bag rated for 30 degrees Fahrenheit. And because this is Florida, you’ll need to bring plenty of sunscreen. You’ll also want sunglasses with a floating strap. (The Gulf is a notorious graveyard of $400 sunglasses and digital cameras.) Headlamps are great for keeping your hands free while still being able to see how to get back to your tent. Another must have are water shoes—the beaches are often shelly and sharp, and fl ip-fl ops might just float away. And, as added protection, light-weight clothing (preferably lightweight long pants and long-sleeved shirts) to combat both the sun and bugs. Last but not least, bug spray.

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