By David Conway, Managing Editor

Islamorada’s fishing is a tale of two towns. You can catch a tuna at 10 a.m. and be fighting a redfish by four that afternoon.

That slim stretch of land halfway down the Keys is a stroke of geological genius for anglers. Only three miles to Islamorada’s south stands the reef, home of snapper and grouper. From there, the sea floor quickly drops off to the continental shelf—and marlin and swordfish grounds. Warm, cobalt Gulf Stream waters often flow near the reef, even over it, and bring pelagics like dolphin and wahoo that much closer to the island.

To the northwest, kings and cobia cruise Gulf waters. To the northeast, Florida Bay’s network of keys, banks and channels that hold tarpon and bonefish gradually morph with the miles to the rich, remote shores of Cape Sable, the Everglades, where inshore game like redfish and snook thrive.

Two days of fishing wouldn’t be enough to even begin to explore both sides of Islamorada, but it would make a good start. Captain James Chappell, a Keys native, and his mate Jeff Peitig would show us the way.

On our first day, we left Chappell’s dock at Bud ‘N Mary’s Marina and ran to the reef, where most bluewater trips in Islamorada begin, for the baits. That quick access to the reef and deep water—only half as far away as in the Lower Keys, where the reef lies about seven miles from the islands—gives small boat owners a big advantage around Islamorada.

Chappell anchored his 32-foot center console, Catchalottafish, upcurrent of a dropoff in 40 feet, and put out the chum. Within minutes, houndfish, snappers, blue runners and speedos gathered in the slick.

“Speedos are the primo baits around here for wahoo, big kings and dolphin, and sails too. They all love ’em,” Chappell said. “Generally, there’s plenty of bait around the islands, and that’s why the pelagics hang around here. When we can’t get speedos, we’ll take out big pilchards, ballyhoo and pinfish, but we fish live baits all the time, year-round in Islamorada. It’s definitely the way to go here. “

“Look at those yellowtail back there,” Peitig said. “There goes a 5-pounder, a couple 3-pounders.”

The yellowtail swarmed near the surface, and I gritted my teeth when we pulled anchor and turned away, but we were after bigger fish.

“We have places where we just crush the yellowtail,” Peitig had to add.

The cranking east wind forced us to scratch our main plans to go out to the Humps, the seamounts off Islamorada and Marathon that rise hundreds of feet off the bottom and draw pelagics, especially blackfin tuna and dolphin, to their currents swirling with baitfish. The Humps, and there are half a dozen out there in depths from 300 to 800 feet between Marathon and Key Largo, are one of Florida’s classic offshore destinations, up there with the Steps off Tampa, the Cones off Canaveral and the Wall off Key West. Not only blackfin and dolphin, but wahoo, amberjack and kings frequent the Humps, and another whole raft of species dwells on bottom, including vermilion and queen snapper, tilefish and snowy grouper—a bottom dropper’s paradise. In one of many neat tricks at the Humps, anglers catch a small blackfin, bridle it up, and troll it out deeper in 2,000 feet for marlin.

But what makes the Humps so productive when the Gulf Stream runs over their bottom structure also makes the trip treacherous in high east winds. With the current hammering into the wind, seas stack up to 8 and 10 feet, rolling in quick succession. Chappell and Peitig looked south and just shook their heads. Not today.

Instead, we loaded up on pilchards at another spot and free-lined them back into a chumslick as we drifted over bottom structure in depths of 150 and 200 feet. Captain James hooks the pilchards in the back of the belly, above the anal fin, so that they dive and attract predators on their way down.

We had good blue water, and tricklings of sargassum weed that might have formed up into a weedline with a slightly lesser wind. It didn’t take long before a king skyrocketed through a bait pod near us, and a gaffer dolphin raced beneath our boat. Fellow Florida Sportsman editor Jeff Weakley pinned a pilchard to a heavy jig and let it bounce on our drifts.

“Hey, whenever everybody’s doing the same thing I do something different to change it up,” he said. “When everybody else zigs, I zag.”

Hoping for a grouper, he plucked up a few sharpnose sharks, until a king cut him off. By then, Chappell had us set for another drift over the spot, an old wreck, and we hooked a good dolphin, brought it to the bow, and tightened its leash. It drew the small school near us, and we snatched another.

“I love the way they hang around the boat in the summer,” Chappell said. “Even in the winter we catch a number of big bulls, around 30 pounds, right here, in 200 to 400 feet.”

We also had an aerial show from big northern gannets that dive-bombed the baits in our chum slick headfirst, like missiles, so fast that a couple of us on the boat instinctively ducked. These are big pelagic birds, the largest of the booby species, and they only come ashore to breed. Chappell told us that the birds migrate through in the spring and stay for about a month.

Following the “big baits, big fish” principle, Chappell called for one of the speedos, and he rigged up a stinger hook with wire, placing the stinger lightly in the bait’s upper back, near the dorsal. Deployed for five minutes, some fish whacked that bait so hard it bent the heavy rod double for a millisecond, before slicing off the whole rig—24 inches of wire included.

“Wahoo,” was the one word we could utter.

To end the day, another speedo went down, and came back minutes later neatly slashed in half, right behind the stinger.

“Big king.”

That’s big fish-fishing. It’s all or nothing, every time.

Later that night, the sight of the gannet came back to me, and how I’d never seen one in Key West, where I’d fished for years. It made me wonder about the differences in those two fisheries, both hot destinations for traveling anglers.

Captain Chappell was the right man to ask. He grew up fishing in Key West, and a few of his buddies are right now among that town’s leading young charter captains, but he chose Islamorada.

“Both are incredible fishing destinations, no doubt,” he said. “Key West has the Marquesas and the Tortugas, and more wrecks and structures to fish than we do in Islamorada. We have a far run to deep Gulf water, but here in Islamorada and Key Largo we have the Everglades and Flamingo areas, plus we’re closer to the Bahamas. We both share the reef, but the main thing to me is, not only is the reef farther away in Key West, but the Gulf Stream generally runs between five to 10 miles farther out in Key West than in Islamorada. That means that the current gets in really close here to create incredible live-baiting situations.”

Captain Skip Nielsen, a veteran Islamorada offshore captain who now concentrates his angling around Sandy Key, Cape Sable and in the Gulf, agreed with those points and added, “I believe that Islamorada offers more bonefishing than Key West, but Key West has better permit fishing. Sailfishing is more consistent in the Upper Keys. Personally, I live here but when I take a vacation I like to travel down the Keys to explore different waters.”

On the second day, our plan to wrangle with big fish would not be shut down, even by gale-force winds. We took refuge from the winds back in the Gulf, where Chappell anchored near a rockpile and chummed up schools of Spanish mackerel, which hang around there through the early spring, depending on water temps. As he retied a line a Spanish had cut, Chappell showed me one of the compartments in his plastic tackle box that he filled with baby powder.

“Keep that baby powder in there and it prevents your tackle from rusting by absorbing all the moisture,” he tipped me off.

Peitig put up the kite, and once we caught a good, lively mackerel, the captain hooked it and sailed it back to attract sharks, big blacktips, spinners and lemons, that hunt those mackerel schools in the Gulf.

In minutes, we had a 200-pound blacktip on the line, pulling 50-pound braid out in hundred-yard lengths like a racehorse. If you like the idea, you can even chum those sharks to your boat on the flats and in channels and entice them to strike a fly. That fishery lasts from the early winter through mid-spring.

Intent on showing us more of Islamorada’s big fish, Chappell had us stock a few more mackerel and we motored east, to Florida Bay, to find true goliaths. On our run, Peitig told me to look for tripletail hanging around the dozens of lobster buoys we passed.

At our spot, a rubble pile almost in sight of Cape Sable, which itself makes a remote and wild fishing and camping spot, we anchored. Chappell said, pointing to the depthfinder, “See those solid red marks? Those are the fish we want.”

Weakley lowered a mackerel on the heavy rig, and held tight. The tip dipped, and he said, “Uh-oh, he’s got it.” The rod stayed bent. “He’s hooked and he doesn’t even care. These fish have no fear.”

The fish moved 20 yards, and only when Jeff leaned on it hard did the fish turn and fight. After a 10-minute standup battle, he raised what had to be a 400-pound goliath, a truly memorable fish, and the biggest of the five that we caught at that spot. To get better big fish-fishing, you’d have to go back to the Jurassic Period.

For the next two hours, the action continued, unceasingly. A king came over the rail, and a school of jacks attacked. Peitig hooked a fish, possibly a king, shark or cobia, that blazed to the horizon and wrapped a lobster buoy and got lost. Weakley hooked a cobia on a freelined pilchard and boated it—the icing on a cool day.

When the fishing slowed after two hours on the same spot, we took our cue and ran back home, happy, tired and impressed.

Only after two days, it was easy to see why, for at least a century now, American anglers have praised Islamorada’s fishing. Zane Grey, one of big game angling’s early pioneers, explored its shores between his exploits around the world. That history as a fishing town, along with its still productive waters, probably gives Islamorada’s chamber of commerce the nerve, and credibility, to put up those signs along U.S. 1 that proclaim their town “The Sportfishing Capital of the World.”

Fitting for a place with so many possibilities, the name Islamorada itself has multiple meanings. In Spanish, Islamorada literally translates into both “purple isle” (for the purple morning glories that long ago covered the island) and “island home.” To us, Islamorada just means good fishing.

FS