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The Mid-Life Slam

The Florida Keys, a 125-mile island chain extending from the southeastern tip of Florida, seemed the ideal destination. The Keys have an incredible abundance of fish. There are billfish and dolphin a quick run offshore, bonefish and tarpon on the sandy flats, redfish and seatrout in the backcountry region, plus snapper and grouper and jacks and scores more species—various sources put the number at 400 or 500, total. No one knows exactly how many; maybe whoever started to count them got caught up in the great fishing and said to hell with the project.

It was a fail-safe plan, because if I didn’t catch the 50, I’d still be spending a week in fishing paradise. With no flaming cake to look at.

Days 1 and 2: It’s a Snap

In Carl Hiaasen’s novel Stormy Weather, Clinton Tyree, the itinerant and partially deranged ex-governor of Florida, has himself lashed to the railing at the apex of the Card Sound Bridge in order to witness a hurricane heading toward south Florida. As I drive over that bridge this late June day I don’t even see a cloud, just an expanse of brilliant blue water extending alongside and beyond Key Largo.

This bridge is one of two vehicle-accessible entries to the island chain. U.S. 1, the Overseas Highway, connects the Keys, which are formed of limestone outcroppings capped by ancient fossilized coral. Some are developed, some are not. Some are so narrow that you can stand in one spot and see both the Gulf of Mexico and the Atlantic Ocean, which the Keys—there are about 800 of them—essentially separate.

My destination is Upper Matecumbe Key and the village of Islamorada (EYE-la-more-AH-duh), about a third of the way down the island chain. Islamorada bills itself as “The Sportfishing Capital of the World,” and few argue the designation. Fishing boats bristling with rods occupy every dock—a wild array of party boats, offshore sportfishing boats, flats boats, cuddy cabins, walkarounds, and center consoles. Mounts of king mackerel and permit and marlin hang not just in tackle shops but in motels, restaurants, bars, and gas stations. Some are outside, so that you can see giant tarpon and great white sharks without leaving your car.

By the time I pull into Cheeca Lodge, my home for the next seven nights, it is near sunset. Cheeca is a large and beautiful resort on the Atlantic side. I am staying at this famous lodge, which I’ll only see early mornings and evenings, because my family will be joining me later in the week (my wife had eight words to say about my adventure—“You’re not going to the Keys without me”—and she and the kids will enjoy the swimming and the snorkeling here while I’m out on the water).

I’ve been traveling all day but I have fish to catch. So after checking in, I grab my rod and walk past the swimmers in the lagoon and the pool, past the outdoor restaurant. I ignore the calypso music emanating from the speakers in the palmettos and the quiet hum of a piña colada blender at the tiki bar. I resist all these temptations because of the other main reason I’m staying at Cheeca—a 525-foot-long fishing pier on the property.

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