We were up early under a dark sky, rubbing sleep from our eyes on the deck of an outboard skiff, wondering if it would rain. Squat gray columns hung over the waterline, grumbling faintly. The wind hammered our faces. But Chokoloskee Bay — shallow and silvery and floorboard flat — was brightening with morning light. As we cast off, a regatta of brown pelicans fell in behind us, tacking along like feathered sloops.

“Are you ready to rock?” This was Captain Bill Blanton, my fishing guide in the Ten Thousand Islands, a 2,000-square-mile mangrove estuary in southwest Florida that’s the Gulf-side doorstep to the Everglades, moments before we shot out of Chokoloskee marina. Under-caffeinated, I muttered assent. Blanton punched the throttle and we roared alive, the wind quickly ripping my hat and sunglasses from my head and depositing them in our wake.

On a map, the Ten Thousand Islands appear like scattered stones along the upper shin of Florida’s boot. “Islands” isn’t quite right. They’re mostly pulverized, uninhabitable mangrove hummocks and Calusa Indian shell-mounds teeming with black flies and mosquitoes and alligators, all of them being slowly devoured by the sea. They comprise one of the largest roadless expanses in the U.S., mile after mile of warm teardrop bays and saltwater flats, prime habitat for snook, redfish, and tarpon – the Grand Slam of fishing in these parts – plus sea trout and crevalle jacks. I had no Grand Slam illusions. I just wanted to catch something, and, if Blanton was game, to do a little literary sightseeing.

This landscape is the backdrop for Peter Matthiessen’s Watson trilogy of novels, based on the true story of an early 20th century frontiersman named Edgar J. “Bloody” Watson (the books were condensed into a 900-page volume, Shadow Country, which won the 2008 National Book Award). Watson, a sugarcane planter, plume hunter, alligator skinner, beloved family man, and likely serial murderer, was gunned down by a group of his neighbors on Chokoloskee Island in 1910, a piece of vigilante justice that serves as the climactic event of Shadow Country. Rumors of Watson’s murders had persisted for years in the Islands — his black farmhands tended to vanish around payday, it was said — but when a white woman’s body turned up gutted and gouged beyond conception, a posse was formed. Watson, who had outwitted more than one lynch mob in his day, misjudged this one. When he stepped off his boat at Chokoloskee, he was, in Matthiessen’s words, “pretty well shot to pieces.”

“If you’ve read Killing Mister Watson, you know the whole story,” said Blanton, referring to the first book of the Watson trilogy, published in 1990. Blanton, who wore a small gray mustache under a head of loose hair that flew all over the place, had fished in the Ten Thousand Islands for 30 years and knew the Watson story mostly by association with his own fishing spots. We’d just flown past Lostman’s Key, where Watson probably killed three people. Around the bend was the Watson Place, a 40-acre Calusa shell–mound island that once held Watson’s home and sugarcane plantation and is now a National Park Service campsite. All that remained was a syrup kettle, where Watson had boiled down his cane juice, and the skeleton of his Model S Ford.

The author fishing the Ten Thousand Islands

It was hard to get my bearings. Each bend in the mangrove looked the same. The air smelled of seawater, and yet we were technically in the freshwater Glades, with a dense tangle of foliage closing in. Blanton killed the engine and let the boat drift on the tide. I picked up a spinning rod and cast into the rolling surf. In the distance, the banks of a mangrove key were littered with clam and conch shells and, it seemed from a distance, the bones of small animals. It was so quiet I thought I could hear fish slither across the trout grass beneath us.

Back towards Buzzard Key, I caught another sea trout and three more crevalle jacks, the biggest topping out around four-pounds. Then the fishing shut off. In the flats near Tom’s Bight, I cast and cast to giant redfish sunning themselves in the shallows, but they wouldn’t budge. Before I knew it, the day was gone. In eight hours, we’d seen just two other boats. My hands ached from all the fish I’d caught, but I hadn’t sniffed a snook or tarpon. At the dock, some fishermen were hauling their boat out of the water ahead of us, and I overheard one of them say: “That was very humbling. Just when I thought I knew how to fish, I came here.”

The next day it started raining, so I drove around Chokoloskee (the word means “old home” in Seminole). The island is a huge shell-midden built by Calusa hundreds of years ago. Connected to Everglades City (pop. 500) by a narrow causeway, it’s a quiet place with a strange, bloody past that would’ve been forgotten if not for Matthiessen. I stopped by the old Smallwood Store, where Watson had been killed back in 1910. Today the store is a museum run by Lynn Smallwood McMillin, the granddaughter of Ted Smallwood, who was friends with Watson. The museum offers “Bloody Watson” boat tours and, until a couple of years ago, staged dramatic reenactments of the killing on the dock out back.

Growing up, McMillin heard incessantly about the Watson legend, and she now repeats the stories several times a day for visitors.

“Matthiessen got it right,” she told me, pointing to the pile of Shadow Country books for sale on the countertop. “His version is pretty much my version. Watson showed up here sometime in 1892, fathered a bunch of children, killed a bunch of people, left and came back. His killings had to stop. When he came back, the men put a stop to him.”

It quit raining, so I packed a day bag and fly-rod and kayaked out to Halfway Creek, which slices through 11 miles of mangrove swamp, ending in the Big Cypress National Preserve. It’s here that Shadow Country begins. Watson’s eventual foreman, Erskine Thompson, recalls his boss’s first appearance in the Ten Thousand Islands. Though uneventful, it didn’t bode well: “That feller would look at you dead on for a long minute, then blink just once, real slow, like a chewing turtle, keeping his eyes closed for a moment, as if resting ‘em up from such a dretful sight. That’s how I first noticed his fire color, that dark red hair the color of old embers or dried blood, the ruddy skin and sunburned whiskers with a little gold to ‘em, like he glowed inside.”

Red and black mangroves swallowed me, arching overhead like a cathedral. I had to lean back to pass under the branches. The water was crystal clear in places and ran over vermillion limestone. White ibis feathers drifted by on the surface. When the trees opened, I cast around, and before long I hooked into something that almost yanked my rod from my hands, swirling my fly-line in boiling water, until my line snapped. I never found out what it was.

About two miles in, a pair of ibis strolled out of the shadows. I paddled in for a photo. I’d never been so close to an ibis and couldn’t get over how red and wrinkled their legs were, how dusty their white feathers looked. Rummaging for my camera, I dropped my paddle, which smacked against the kayak hull and splashed into the water. The ibis looked up, raised their wings, honked, and flapped off, seeking the darkness of the swamp.

If You Go

What to do, where to stay, and what to eat.

The Wilderness Waterway: This 99-mile-long canoe and kayak route extends from Everglades City to Flamingo, at Florida’s southern tip. There are 47 beach campsites and “chickees” — raised wooden platforms — along the way. Nautical charts and a GPS are essential. Without them, you’re a gator appetizer. The less adventurous can tackle Halfway Creek, the Turner River, or Sandfly Island in half a day. Kayaks and canoes are available at Everglades Adventures. By far the best, if most expensive, way to fish the Ten Thousand Islands is to hire a knowledgeable local guide.

The mangroves are low and dense so a kayak or canoe is the transport of choice.

The Everglades Rod & Gun Club: Dating to the 1870s, the Rod & Gun Club has served as a kind of gilded fishing shack over the years to everyone from Ernest Hemingway and Sean Connery to Harry Truman and Burt Reynolds. It’s a time capsule of Old Florida, with dark hardwood floors, leather armchairs, a smoky brick fireplace, ample taxidermy, poor lighting despite all the Tiffany lamps, and a vast screened veranda overlooking the Barron River (men have caught 150-pound tarpon from the dock). The last time I visited, they still only accepted cash or checks and the swimming pool was on the fritz, but the margaritas were mixed, shaken and topped up at my table; the shrimp cocktail was as big as an outboard motor; and my cabin’s shower was more spacious than most New York City apartments. Learn More

Camellia St. Grill: Without question the best restaurant in Everglades City and Chokoloskee, and arguably all of Southwest Florida, Camellia’s is an incongruous spot, tucked back on a bend of the Barron River amongst a cluster of fish-packing plants, in a town with few other options besides Circle K potato chip rack. By comparison, everything else south of I-41 is like rummaging through a garbage can. Camellia’s cooking falls somewhere between Southern and Caribbean, with perhaps a splash of Texas Hill Country. My last time, there I started with the stone crab claws and moved onto the spare ribs, then tied everything together with a platter of fried oysters and a slice of key lime pie. I couldn’t believe my luck, sitting beside the fast-moving river with egrets and spoonbills romping through the treetops, a long long day of fishing behind me, oysters stretching to the horizon, and more beer on the way. Learn More