ISLAMORADA, Florida Keys — The fisherman’s paradise known as Islamorada was incorporated as a municipality in January 1998. Now called Islamorada, Village of Islands, the village that measures 20 miles long and, in some places, barely 150 feet wide encompasses Plantation, Windley, Upper and Lower Matecumbe keys.
Legend has it the area was named by Spanish explorers who, seeing the purple sky at sunset and the purple bougainvillea, used the words “isla” and “morado” or purple island.
It’s probably more likely that the area was named by William J. Krome, the primary surveyor for the Over-Sea Railroad that traversed the Keys. Trains would only stop at named towns, so Krome is said to have christened the location on Upper Matecumbe Key “Islamorada,” after the schooner Island Home owned by the pioneering Pinder family.
Known as the Sport-Fishing Capital of the World, Islamorada is where backcountry sport fishing and saltwater fly fishing were pioneered. It’s where legendary fishing figures including Ted Williams, Jimmy Albright, and Cecil Keith plied their trade. Perhaps the world’s highest density of professional offshore charter boats with tournament-grade captains can be found in Islamorada.
Islamorada’s unique location, lying between Florida Bay (the “backcountry”) and the Atlantic Ocean (the “front side”), provides an unrivaled diversity of fishing opportunities. The Gulf Stream flows past the islands from 10 to 20 miles offshore, bringing seasonal visitors like sailfish and marlin, kingfish and wahoo, dolphin (mahi-mahi) and tuna close enough to shore to be targeted by small-boat anglers. Tarpon and bonefish are among inshore species coveted by light tackle anglers.
Scuba divers and snorkelers flock to the region to explore the extraordinary reef line and patch reefs brimming with tropical fish, sponges, soft and hard corals and crustaceans. Davis, Conch, Alligator and Pickles reefs, Crocker Wall and the Aquarium and Fish Bowl offer safe and easy viewing of Islamorada’s diverse marine life for divers and snorkelers of virtually every skill level.
The intentionally scuttled 287-foot Eagle is Islamorada’s premier artificial reef. The wreck sits on a 105-foot-deep sandy bottom but its superstructure can be enjoyed and explored at depths of 60 to 70 feet. In the San Pedro Underwater Archaeological Preserve, divers and snorkelers can see the remnants of a wrecked 1733 Spanish treasure fleet galleon at depths of 15 to 20 feet.
On land, travelers can step inside a coral reef to see 20,000 years of reef development at the Windley Key Fossil Reef Geological State Park. Lignumvitae Key Botanical State Park, a short ride by boat, encompasses a virgin hardwood hammock untouched by modern development as well as the original Matheson home built in 1919.
The Islamorada area also features eco-tours, water sports such as standup paddling and kiteboarding, tennis facilities, bicycle trails, historic hikes, beautiful vistas of both the Atlantic Ocean and Florida Bay, opportunities to swim with dolphins and stingrays, and a typically quirky Keys recreational activity: hand-feeding tarpon off the docks at Robbie’s Marina, mile marker (MM) 77.5 bayside.
Area beaches include a family facility with picnic tables behind the Islamorada Public Library and Anne’s Beach, where stretches of sand are linked by a boardwalk nature trail.
Islamorada also is home to the Morada Way Arts & Cultural District, spotlighting the art galleries and restaurants at Morada Way between mile markers (MM) 81 and 82. As well as welcoming visitors throughout the year, the popular arts district is the site of the Third Thursday Art Walk each month that features fine art, live music and culinary offerings.
Local restaurants range from very upscale continental to casual to downright funky. Many specialize in fresh-from-the-dock seafood, while others offer steaks, gourmet or ethnic dishes and even pizza and hamburgers.
Islamorada is about a 1.5-hour drive from Miami International Airport and a 40-minute drive from the Florida Keys Marathon Airport in the Middle Keys.
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Anne’s Beach, MM 73.5 oceanside. Situated along the roadside, Anne’s Beach is a popular spot for sunning and swimming. A boardwalk through mangroves links two sandy areas. Clean and spacious restrooms are available. Covered picnic structures can be found along the length of the boardwalk.
Florida Keys History of Diving Museum, MM 83 bayside; 305-664-9737, One of the world’s largest collections of historic dive equipment traces 3,000 years of diving. A special gallery features artifacts and recovery tools used by pioneering treasure hunter Art McKee. The “Parade of Nations” features historic dive helmets from some 25 nations.
Florida Keys History and Discovery Center, MM 82 bayside; 305-664-2031, The Discovery Center is part of Islander Resort, a Guy Harvey Outpost, located at 82100 Overseas Highway. Dually purposed as a conference center, the venue is dedicated to showcasing the history, environmental and marine conservation efforts of the Florida Keys in a series of state-of-the-art exhibits.
Hurricane Monument, MM 81.6 oceanside. The 65-foot by 20-foot art deco–style Hurricane Monument commemorates veterans and locals who died during the Labor Day Hurricane of 1935. Beneath the tiled mosaic that forms the base of the monument are the ashes of many who died in the storm.
Indian Key Historic State Park, offshore near MM 78.5 oceanside; 305-664-2540, Visitors to this 11-acre island can view the remains of a wrecking, or shipwreck salvage, community from the 1830s. There are also several hundred yards of well-maintained trails that line the interior of the island.
Islamorada Library Beach, MM 81.5 bayside. Located behind the Helen Wadley Branch library, this small beach offers picnic facilities.
Lignumvitae Key Botanical State Park, offshore near MM 78.5 bayside; 305-664-2540, Accessible only by boat, the island features a virgin hardwood hammock, along with an early Florida Keys pioneer family home and a stone wall believed to have been built by Native Americans. A boat runs to the island from Robbie’s Marina, MM 77.5 bayside in Islamorada. Tours can be arranged through Robbie’s.
Long Key State Park, on the Atlantic Ocean at MM 67.5, 305-664-4815, The Spanish named this island "Cayo Vivora" or Rattlesnake Key because its shape resembles a snake with its jaws open. In the early 20th century, Long Key was the site of a luxurious fishing resort that was once the winter home to writer Zane Grey. Today, visitors can explore this island by canoeing through a chain of lagoons or hiking two land-based trails. The Golden Orb Trail leads visitors through five natural communities to an observation tower that provides a panoramic view of the island and its profusion of plant and animal life. Some of the best bonefishing in the Keys is found here. Full-facility campsites overlook the Atlantic Ocean.
Pioneer Cemetery, MM 82 oceanside. Situated on the beach adjacent to Cheeca Lodge, the cemetery is the final resting place of Islamorada area pioneers.
Robbie’s Marina, MM 77.5 bayside; 305-664-9814, Visitors can purchase buckets of bait to feed tarpon from the marina dock. Small shops sell T-shirts and island crafts. Fishing and snorkeling excursions and state park tours can be booked as well.
Theater of the Sea, MM 84.7 oceanside; 305-664-2431, Visitors can swim with bottlenose dolphins, stingrays and sea lions; enjoy wild animal exhibits and view parrot, dolphin and sea lion shows at this attraction, the second oldest marine mammal facility in the world.
ICE Amphitheater at Founders Park, MM 87 bayside; 305-853-1685, This outdoor performing arts amphitheater features six concrete rows of seats that accommodate approximately 300 people and open “festival” seating on the grass that accommodates up to 4,000. Musical concerts, dance and other live performances highlight a yearly show schedule.
Windley Key Fossil Reef Geological State Park, MM 85.5 bayside; 305-664-2540, An exposed coral reef, this park once served as a quarry for construction of the Key West extension of the Florida East Coast Railway. Later, the quarry yielded decorative building stones. An environmental center documents park and regional history, and self-guided nature trails wind through mangrove hammocks.
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