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It’s 7 a.m., and I’m standing on the front of a skiff, trying to keep my balance as waves lap against the fiberglass hull. The sun is illuminating multiple shades of blue that stretch to the horizon. Behind me, on a tall platform, a guide silently poles the skiff over the sandy backcountry flats off Islamorada in the Florida Keys, searching for signs of fish. Suddenly he breaks the calm. “Monster at nine o’clock,” he shouts. I turn and look where he’s pointing. About 25 feet away I can make out a faint ripple on the surface, and there beneath it is the dark outline of a large tarpon. And he’s moving toward us — fast. He’s swimming snout-down, kicking up a brownish trail of silt as he probes the bottom for food. “Lay the fly in front of his nose,” the guide says. “Let’s GO!” I pick up the fly and flick it back and forth in the air, paying out line. My first presentation of the lure hits the water behind the still moving tarpon. Now it’s only 10 feet away. I quickly yank the line out of the water, but the big fish spooks, leaving just a cloud of muck as he races away. I smile as my adrenaline ebbs: Even the misses are worth the trip. And the wonder of fishing out of Islamorada is that you get so many of those chances that at least one time you’ll put the fly just right and have a big tarpon jumping out of the water like a 120-pound grasshopper. Or you can go after schools of bonefish, pound for pound the best fighters in the sea. If fly fishing isn’t your thing, Islamorada also offers the option of heading out to sea for big game. There you can crack open a cold beer while you troll for a hulking yellowfin tuna or sailfish. The two are a study in contrast. When a sailfish hits a surface bait, he runs away like he stole something. With the reel humming and line flying out, you slap down the drag and set the hook. That’s when all hell breaks loose. Out from the water he’ll fly, desperate to escape. Tuna, on the other hand, hit the line and head for the bottom, dropping like a sack of bricks. Then comes 30 minutes of biceps-numbing reeling and tugging until he decides to give up. You also might get some luminescent dolphin (the fish, not the mammal, also known as mahi-mahi), considered among the best-tasting catch in the sea, or wahoo, whose name says it all. And out there in the cold currents somewhere is also the king of all game fish, the marlin, who may deign to pay you a visit if the mood and the weather suit him. It’s this variety of fishing and plenitude of fish that leads Islamorada to proclaim itself the “Sportfishing Capital of the World.” And while Key West gets more press for its nightlife and island style, Islamorada can more than hold its own in that category as well. One of the unique qualities of this town of 9,000 is that the vast majority of businesses are still privately owned — only a few chains have gained a foothold on the island — so Islamorada still maintains a local flavor. There’s plenty of cuisine to keep a gourmand happy, including some of the best seafood in Florida: Manny & Isa’s (Tel. (305) 664-5019) has a Cuban flavor with the additional treat of wonderful Key lime pie, while Uncle’s (Tel. (305) 664-4402) offers a larger wine list and a more upscale Mediterranean feel. Kaiyo (Tel. (305) 664-5556), a sushi restaurant, and Pierre’s (Tel. (305) 664-3225), with its romantic beach atmosphere, are two upscale newcomers to island dining. The Moorings Village (Tel. (305) 664-4708; and the Cheeca Lodge (Tel. 800-327-2888;, located on neighboring beachfront properties, offer plush seaside accommodations. The Moorings Village has one-, two- and three-bedroom houses and cottages where a pool and a private beach are footsteps away. Cheeca Lodge began as a private fishing lodge but now serves as a waterfront 203-room hotel with a par-three golf course, a spa and a good restaurant on the premises. Island Villa Properties (Tel. (305) 664-1333; offers vacation homes that are perfect for large groups and families. ARRIVING: Fly into either Fort Lauderdale or Miami and rent a car or get a car service to pick you up (Luxury Limousine, Tel. (305) 664-0601). Fort Lauderdale adds about 30 minutes to the driving time, but it offers cheaper flights and is easier to work around because of its smaller size. WHOM TO CALL: Most of the best backcountry guides fish out of the Lor-e-Lei Marina (Tel. (305) 664-4338; Captain Randy Towe (Tel. (305) 394-2667;, on his boat, Quit Yer Bitchin, is a wonderful offshore guide. WHEN TO GO: The bonefishing is good all year but peaks from September to March. The tarpon move onto the flats in April and stick around through July. November through March brings sailfish into the area. Yellowfin tuna migrate spring through the summer, and mahi-mahi and wahoo are around all year.

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