Islamorada Fishing

If you want a relaxing vacation laying on the beach with hours and hours of leisure time to dream and soak up the sun, Islamorada is a great choice. But most people who visit this small town in the Upper Florida Keys have something else on their minds, involving lots more action, and that’s salt water sport fishing. In fact, if you want to just relax on your vacation, don’t even think of doing any Islamorada fishing: you will be pretty tired out at the end of the day, from fighting all those fish.

Everyone knows Islamorada is called the Sport fishing Capital of the World. It’s as famous for salt water sport fishing as Key West is famous for its sunsets. There are hundreds of Islamorada fishing guides to choose from, and several types of fishing you can try. From the skinny waters of Florida Bay to offshore currents in the Gulf Stream, there are so many ways to enjoy fishing in Islamorada you could spend weeks here or more, and still feel you haven’t experienced all of it. Maybe that’s why so many anglers come back for more Islamorada fishing year after year.

Islamorada fishing charters go out of a few main marinas: World Wide Sportsman, Bud ‘N Mary’s, Holiday Isle, and Whale Harbor. All of these are visible from the Overseas Highway, or Route 1, the main drag through the Florida Keys.

Things to Do in Islamorada

Things to do in Islamorada include of course world-class fishing but also some other attractions, too. Islamorada is actually a chain of islands between Key Largo and Marathon, running from Mile Marker 88 to Mile Marker 73 (Marathon is at MM 50). It includes the Keys called Matecumbe, Windley, and Plantation, whose residents state on their address forms that they live in Islamorada. It’s known as the Sportfishing Capital of the World, but there are some things to do in Islamorada for land-lubbers as well.

Theater of the Sea

Theater of the Sea is one of those showy, grab you as you go by large tourist attractions you just hope your kids won’t spot from the back seat of the car as you speed by with your fingers crossed. You really can’t miss it with its gigantic sculptures out front depicting critters and shells. The grounds are pristine and sharply landscaped, with shrubs trimmed into shapes of dolphins. The parking lot is at times dominated by sleepy, nonchalant cats basking in the sun or refusing to give up parking spaces. The attraction itself offers, among other things, swim with the dolphins. You can also swim with the sting rays if you’re on a budget because it’s much cheaper. Those poor underpaid sting rays! Theater of the Sea is one of the best things to do in Islamorada if you have kids.

World Wide Sportsman

You ask, how could a tackle store be listed under Islamorada Attractions? The answer is that the World Wide Sportsman is so much more than a tackle store. It’s a grand resort of all things fishing, fish, and boating. It’s got a cafe, a restaurant, a marina, rockers on the porch overlooking the bay, a glass elevator, a giant fish tank, and a replica of Ernest Hemingway’s boat Pilar, which you can climb up into and have a look around if you like. All this is in addition to rows and rows of fishing clothing, sunscreen shirts, a ladies boutique upstairs next to yes, the Art Gallery! The footwear section is fascinating if you like all sorts of Crocs and flip flops, not to mention deck shoes. There’s a snorkel and lobstering section where you can get ready for the Lobster Season. The gift section in front has a faux fireplace and wing chairs in the book store area, and more gourmet sauces, fish rubs, and fry batters than you can shake a stick at. After fishing, World Wide Sportsman is perhaps next on the list of most popular things to do in Islamorada. It’s really something to see, and you’ll also probably find something you need, even if you don’t fish.

More on Indian Key

Indian Key has eleven acres of land on it, and in the heyday of the Florida Keys wrecking industry, in the 1830s, it was private village of sorts. Jacob Houseman started the personal town so he wouldn’t have to follow wrecking industry rules and regulations of Key West. He even had a Post Office and a bowling alley. Audubaon spent time on a large boat just off Indian Key, discovering new birds such as the roseate tern. He and his art partner George Lehman, who did the landscapes while Audubon did the birds, spent time here drawing cormorants, egrets, and the like. Audubon shot lots of birds so he could stuff them and wire them into poses for artistic renderings later.

Jacob Houseman had connections or money, because he was able to get the Navy to put a fleet of ships off Indian Key to protect his village from Seminole Indians. Caloosa Indians had supposedly had massacred 400 shipwrecked Frenchmen on the Island a while back. The Navy fleet turned out to like drinking a whole lot more than protecting Jacob Houseman’s island, however. The whole village except for the postman’s house, was burned to the ground in 1840 by the Seminoles. They also killed over a dozen people. Jacob Houseman had to go back to Key West and make a living as a worker on a rival wrecker’s boat. It only lasted six months until he died in an accident on board. He’s bured at Indian Key and if you visit the island you can read the historical plaque marking his gravesite.

Another settlement was formed on Indian Key thirty years later, and schooners were built here. This was around the time when the Alligator Reef lighthouse was being built, so workers lived on Indian Key as well.

In the 1930s and 1940s, people dynamited Indian Key looking for treasure. The island is kind of messy looking because of this, and looks nothing like the natural beauty of Lignumvitae Key, which has been preserved. You are allowed to visit Indian Key, and hours are 8 am to sunset. It’s at Mile Marker 78.5. This is one of the more popular things to do in Islamorada if you love the water or nature.


Islamorada: if you want to visit the Sportsfishing Capital of the World, you don’t have to go any further than here, the “purple isles”, named for the violet sea snails in the area. Located on Upper Matecumbe Key, the Islamorada area actually spans from Long Key to south Plantation Key, covering an area of about twenty miles.

Islamorada’s claim to fame is its world class sportsfishing. Islamorada has been the place of more world record size catches than anywhere else in the world. It is also believed that Islamorada is home to more fishing boats per square mile than any other place in the world.

The Florida Bay, located off the southern tip of Florida between the Gulf of Mexico and the Atlantic Ocean, features 30 square miles of shallow depths and small islands, making it the ideal place for backcountry fishing in shallow hulled boats. Tarpon, permit, redfish, trout, snapper and snook are among the most popular sportfish caught in the Bay. With shallow depths ranging from 5 to 10 feet in month places throughout the Florida Bay, it offers world class fly fishing for anglers.

Offshore, anglers can find marlin, sailfish, shark and dolphin.

There are also plenty of local activities for non-anglers in the groups around Islamorada. Walking tours of Lignumvitae Key State Botanical Site are given four days a week, with access by a short fifteen minute boat ride from Robbie’s Marina.

Indian Key State Historic Site is an 11-acre island also accessible by a short boat ride from Robbie’s Marina. Rangers offer 90 minute guided tours of Indian Key, revealing the interesting history of the island as a wrecking station and once home to a city, complete with a hotel, for the islands 50 permanent residents. There are several other points of interest in Islamorada and the Upper Keys for anglers and non-anglers alike.

Hospitality on Islamorada is well known and genuine, and many guests return year after year. Accomodations on Islamorada range from pitching a tent at the Long Key State Recreation Area to one of the upscale spa and resorts.

The Fiesta Key Resort KOA offers hookups for RVs, motels start in the $50 to $75 range, and resorts such as the Cheeca Lodge and Spa can run several hundred dollars a nite or more.

Locally run bed and breakfasts are available for those looking for a more personal or intimate touch, and even some houseboats are available for guests to rent, for those who want to experience living on the water in Islamorada as well. Houses and condos are also available, and are the perfect choice for those planning on staying for a month or longer.

La Jolla Resort

La Jolla Resort in Islamorada features pleasant cottages set amidst lush tropical foliage at the edge of Florida Bay.  If you’re gearing up for a fishing vacation in the Florida Keys, La Jolla Resort will seem like the perfect vacation spot, with its boat ramp, docks, fishing pier, and the fly-tying desk in their new Sportsmans’ Lounge.  The owner is a fishing guide, so anglers will feel right at home staying in a resort designed by a fellow salt water sportsman.

Accommodations at La Jolla Resort are neat little cottages with kitchens, ranging from one to three rooms.  Some face Florida Bay and others are closer to the pool, euphemistically called “Garden Rooms”.  Whichever cottage you find yourself in, you’ll be pleased with the cleanliness, attractive renovations, and lush surroundings. This is a perfect place to stay if you have a Cheap Flights to Florida

Tropical vegetation includes a wonderful variety of  palm trees, key lime trees, bromeliads, hibiscus,  frangipani and bougainvillea.  For anyone in need of a tropical vacation, the vegetation alone at La Jolla Resort will restore the soul and put you at ease immediately.  The Florida Keys are known for casual atmosphere, which means a slower pace, less stress, and an overall calming environment, whether it’s swinging from a hammock at the water’s edge under the warm tropical sun, or zipping around in the back country on a day of Islamorada fishing.  The folks at La Jolla Resort have done an excellent job of creating an oasis getaway for travelers in the Florida Keys.

Chesapeake Resort

The Chesapeake Resort in Islamorada offers visitors to the Florida Keys a wonderful respite amidst heavenly surroundings and a private beach.  You don’t have to drive far to reach Paradise, and with the Chesapeake Resort, you’re there in less than two hours from Miami International Airport.

Chesapeake Resort is located on the Ocean side of Islamorada, so you get fabulous views from the water view rooms and villas.  The beach is gorgeous, and grounds are newly renovated, as are the rooms.  Families or groups can feel the comforts of home while on tropical vacation in one of thirteen villas equipped with full kitchens, splendid bathrooms and plenty of space to stretch out and live your dream vacation.

Step out onto your private terrace if you choose a villa, or even if you opt for one of 44 guest rooms or 8 suites in the main building.  Large HDTVs in rooms are new, and phones have data ports in case you don’t want to leave the real world entirely behind you while you’re in Islamorada.

After a day of water sports, charter fishing that leaves from the private Chesapeake Resort docks, or just lazing on the beach, you can enjoy the oceanfront hot tub or heated swimming pools.  Or how about watching the night sky from a Tiki hut observation deck?  We think you’ll agree the newly renovated Chesapeake Resort is better than ever!

Islamorada Hotels

In Islamorada, visitors have the best of all worlds on vacation.  Only an hour and a half from Miami International Airport, the city of Islamorada is close to everything yet offers a remote and peaceful setting for a restorative getaway vacation in the Florida Keys.  Islamorada hotels offer retreats within the peaceful resort town of Islamorada, with several excellent choices – many of which will not break your travel budget.

We offer an in-depth look at each of the Islamorada hotels we cover here, and booking information, discounts, and pictures.  We can tell you whether a certain Islamorada hotel is better for the serious angler, which have the better spa services, and which Islamorada hotels you can count on for great service, super amenities, or deep discounts.

Islamorada is a city of islands, starting at Mile Marker 88 after Key Largo and Tavernier, and ending around Mile Marker  78.  There are six islands in Islamorada, Plantation Key, Windley Key, Upper Matecumbe Key, Lower Matecumbe Key and the offshore islands of Indian Key and Lignumvitae Key. Islamorada hotels can be found on several of these islands, on the Overseas Highway.

Islamorada offers lots to do, above and beyond the world class fishing that’s made the city so famous.