Islamorada is a village located in the Florida Keys, in the United States of America. Islamorada has the great reputation of being “known as the “Sportfishing Capital of the World” and rumor has it that it hosts the largest fishing fleet per square mile than anywhere else in the world. This perfect family vacation destination offers something to do in, under, above or near the water 24 hours a day. The aqua blue waters surrounding this “Village of Islands” provide fantastic views from every bridge and waterfront resort and restaurant. And the seafood is as fresh as it can be” (VisitFlorida). Islamorada has established a name for great food, beautiful waters, and an overall wonderful place to vacation.

Islamorada History

Looking at the history of Islamorada, “The name Islamorada (“purple island”) came from early Spanish explorers in the area. Its pronunciation has been Anglicized to aisle-a-more-AH-dah. Islamorada was hit almost directly by the Labor Day Hurricane of 1935, causing 423 deaths.[2] A memorial, including the ashes of over 300 victims, exists today at Overseas Highway mile marker 82. Hall of Fame baseball player Ted Williams began visiting Islamorada in 1943 and for the next 45 years was the island’s most well known resident.[3] After his retirement from baseball he became the national spokesman for Sears sporting goods and became renowned for his abilities as a fisherman. Over the decades, he hosted numerous celebrities at his Islamorada house and took them on local fishing trips. Williams’ residency in Islamorada ended in 1988 when he moved to Hernando, Florida. Williams cited the island’s increased development as his reason for leaving. He reportedly said that he knew it was time to leave when he could no longer make a left turn on to U.S. Route 1 because of the traffic.[4] The village was incorporated on November 4, 1997. Prior to this date, Islamorada was only considered to be on the island of Upper Matecumbe Key. As of the 2010 census, the village had a total population of 6,119. As of 2009, the population recorded by the U.S. Census Bureau is 6,435.[5] (Wikipedia, Islamorada).

Islamorada has been written about by many journalists and travelers. For example, Benna Crawford, writing about Beaches at Islamorada, Florida, says of Islamorada: “Islamorada is a village made up of a string of islands in the Florida Keys. This major sport fishing destination, like the rest of the keys, has sandy strips along the Atlantic and Gulf sides of the Overseas Highway, Route 1, that form narrow beaches. The water is warm, fairly calm and generally shallow along the keys, so beaches are family friendly. Islamorada’s beaches are adjacent to a resort, a library, a marina, a boardwalk and a campground.”

Others have iterated the beauty of Islamorada. For example, The Florida Keys & Key West website writes “Situated between the saltwater wilderness of Everglades National Park and the deep blue waters of the Florida Strait is Islamorada, made up of six islands: Plantation Key, Windley Key, Upper Matecumbe Key, Lower Matecumbe Key and the offshore islands of Indian Key and Lignumvitae Key. Perhaps the world’s highest density of professional offshore charter boats with tournament-grade captains can be found in Islamorada, a village of islands where backcountry sport fishing and saltwater fly fishing were pioneered.” They go on to say that “Islamorada may be the only place on Earth where it is possible to catch a sailfish offshore and pursue bonefish, permit, tarpon, snook and redfish in just inches of water in the backcountry, all in the same day. Islamorada’s identity means much more than sport fishing capital of the world. Travelers on group tours through the Florida Keys — multi-generation families, reunions, seniors, foreign or special interest groups — can find unique experiences, soft adventure and quality. Activity, fun and relaxation for the whole family includes hand-feeding hungry tarpon at the docks of Robbie’s Marina, or catching a dolphin, sea lion and parrot show at Theater of the Sea marine mammal park.”

Kate Maxwell, of Condé Nast Traveler, has written an excellent piece on the Florida Keys and within the Florida Keys, Islamorada, entitled The Perfect Road Trip Through the Florida Keys. In the article, she speaks time writing about her travels through south Florida and the Florida Keys. Within this, she also makes an important stop in Islamorada. Traveling to Islamorada, Kate Maxwell wrote:

“The village of Islamorada actually comprises six tiny islands, so give yourself time to explore. It’s known as the sportfishing capital of the world, so it’s no wonder the seafood restaurants are as good as they are—in fact, they’re destinations in their own right. If you’ve come to fish, sign up for a four-hour trip aboard theCapt. Michael, which sets sail from Robbie’s Marina on the bay side of Islamorada—even amateurs will hook some tarpon in these teeming waters (305-664-8070; fishing trips from $40 per person). Diving is huge down here—to see just how huge, visit the History of Diving Museum. It contains an astounding number of marine artifacts, including bell helmets and armored diving suits, and is the largest collection of its kind in the world (305-664-9737). Beaches, on the other hand, aren’t the big draw in the Keys: The water tends to be shallow because of the coral reefs, and there’s not much wave action. Still, go to Anne’s Beach if you want to put your toes in the sand. It’s wonderfully secluded, and the water is crystal clear and warm year-round.”

And other prestigious magazines such as GQ have also wrote stories on Islamorada. For example, in a 2011 article, Stan Parish of GQ wrote an article entitled “Rad Island: Islamorada, Florida Keys“. In the piece, Parish writes: When the temperature drops, tourists flood Miami. That’s when locals in the know take a quick road trip to Islamorada, a chain of secluded islands in the Keys with a hotel tucked into the tropical shoreline, seafood carried from the beach to your plate, and a never-ending flow of frozen drinks.” Parish discussed the trip to Islamorada and the Florida Keys from Miami, saying that “[i]t’s basically a straight shot from Miami International to the end of mainland Florida. The commercial sprawl of Miami-Dade County falls away after a few miles, and as soon as U.S. 1 becomes the Overseas Highway, you sense a palpable shift to Island Time. Ninety minutes after dropping the top on your rental Camaro convertible, you find yourself on a sliver of land halfway down the Keys.” Parish goes on to write that

“To see the Keys, you need to get out on the water. Skip the Jet Skis and rent a kayak or stand-up paddleboard to glide through the tidal channels in the mangrove islands while tropical fish and lazy manatees swim below you. Islamorada is a bonefishing mecca, but if you’re not an avid Orvis customer, book a spot on the party boat from Robbie’s Marina for a sunset cruise followed by five hours of reef fishing and downing ice-cold $2 beers. Once you’re back on solid ground, the nightlife quiets down. Islamorada bars are meant for making friends while shooting pool (The Whistle Stop) or taking in a sunset so vivid it looks Photoshopped (Lorelei Cabana Bar). Just go easy on the frozen drinks; you’re here to escape the hangover of everyday stress, not wake up with one induced by daiquiris.”

Islamorada has a number of excellent hotels and restaurants. In fact, some, such as Marker 88, have been written about for decades. For example, in 1986, Walter Login wrote a piece in the New York Times about the Islamorada restaurant entitled Eating Well in the Keys. Writing about Marker 88 in Islamorada, Login wrote that “The restaurant called simply Marker 88 looks like something out of a Somerset Maugham South Seas novel with enough palm trees and white sand for Sadie Thompson and an occasional tropical rainstorm to complete the picture. Inside is what is considered the best restaurant in the Florida Keys, the string of emerald and bone white islands that curve southwestward from the southern tip of Florida along 110 miles of U.S. 1 and over 42 bridges to Key West.” He went on also say that ” It gets its name from its location at mile marker 88 on Plantation Key, 88 miles from Whitehead and Fleming Streets in Key West where a sign reads, ”End U.S. 1,” and where mile marker 0 stands, the marker from which all road distances in the Keys are measured. This puts it four miles above Islamorada, 10 miles below Key Largo. There is, however, no marker 88 directly outside the restaurant. The marker is about 20 yards up the road, but there is a little sign in front of the restaurant that reads, ”Gourmet Restaurant.””

Famous Residents in Islamorada

Islamorada is also known as the home of many famous celebrities over the years. For example, of the most noted people to live in Islamorada was the Major League Baseball great Ted Williams. According to, “Mr. Williams moved from Islamorada in 1988 and died at the age of 83, July 5, 2002. Without referring to anything ghostly in nature, a great deal of him can still be spotted around Islamorada, mostly on Upper Matecumbe Key where his pictures adorn the walls of several local businesses like the Green Turtle and Mangrove Mike’s.”

As it has been written in Esquire, Ted Williams “…made his home in Islamorada, bought a little place on the ocean side, with no phone and just room for one man and gear. He’d wake before dawn and spend the day in his boat, then come in, maybe cook a steak, maybe drive off to a Cuban or Italian joint where they served big portions and left him alone. Then, back home, he’d tie a few flies and be in bed by 10:00. He kept it very spare. He didn’t even have a TV.” The Esquire article goes to discuss Ted Williams’ interest in fishing in Islamorada, saying “In Islamorada, he was out every day, fall, winter, spring. He wanted the most and biggest — bonefish, tarpon, salmon — he called then the Big Three. He wanted a thousand of each, and kept books on his progress. He thought fishing and talked fishing and taught fishing at shows for Sears. He felt the joy of the sport, still.” In fact, according to an article in the Sun-Sentinal,Ted Williams “…had come down to Islamorada after the war, looking for work. He did various things to keep body and soul together…” and he was said to be “an artist” once he began guiding.

Others, such as the esteemed writer Ernst Heminway, also had ties to the Florida Keys (living in Key West, in the Florida Keys), while also having some relation to even Islamorada. Ernst Hemmingway’s relationship to Islamorada is based on his writing of a hurricane in the region; Hemingway wrote about the tragic 1935 Hurricane in Islamorada. According to reports, on “Sept. 7, 1935, Ernest Hemingway penned a letter to his editor and friend, Maxwell Perkins. He wrote, “We were the first in to Camp Five of the veterans who were working on the Highway construction. Out of 187, only 8 survived. Saw more dead then I’d seen in one place since the Lower Piave in June of 1918.” He described Indian Key as, “…absolutely swept clean, not a blade of grass, and over the high center of it were scattered live conchs that came in with the sea, craw fish, and dead morays. The whole bottom of the sea blew over it.” “He also stated, “…we made five trips with provisions for survivors to different places, but nothing but dead men to eat the grub. Max, you can’t imagine it, two women, naked, tossed up into trees by the water, swollen and stinking, their breasts as big as balloons, flies between their legs… recognize them as the two very nice girls who ran a sandwich place and filling-station three miles from the ferry.”

Islamorada is a fantastic paradise right in the hear of the Florida Keys. There are many wonderful activities in Islamorada, and thus, there is potential for endless fun! For example, Mommy Poppins Travel put together an excellent article entitled Islamorada, Florida with Kids: Top 15 Things to Do on Your Family Beach Vacation. The list is quoted below:

“1. Eat at Lorelai’s. This place was the epitome of vacation fun. There’s a giant fiberglass mermaid in the parking lot. The kids ran free. The drinks flowed. There was a band, an amazing sunset on the bay, and many, many laughs.

2. Visit Theater of the Sea and swim with dolphins, rays and sea lions.

3. Head to Anne’s Beach for some solitude and hermit crab chasing.

4. Rent a boat. We brought our own lunch and all of us, including the kids, were able to snorkel and fish. Just tooling around on the boat, and taking in the beautiful vistas was wonderful. Prices vary from marina to marina, but it’s approximately $225 for two hours with a captain.

5. Check out Founder’s Park for all types of water and land fun.

6. Take a boat out to Indian Key for a hike, picnic, or change of scenery.

7. Shop local and browse the shelves at Hooked on Books. There’s a nice children’s section if your kids read through what they packed.

8. Drive to Key West, rent a bike, and look for six-toed cats. About 2 hours from Islamorada.

9. Take a ranger-guided tour of Lignumvitae Key Botanical State Park.

10. Feed the Tarpon at Robbie’s Marina. These giant fish will eat right out of your hands, although they are disarmingly large. We did this twice and the kids loved it. The pelicans and herons also enjoy getting in on the action. It’s adjacent to the Hungry Tarpon restaurant, which had great conch stew, fish tacos, and outdoor seating bayside. There’s also a tchotchke market, good for shell anklets, which make 7-yo girls happy.

11. Boat out to San Pedro Underwater Archaeological Preserve State Park and see a shipwreck from 1733.

12. Rent a kayak and check out the mangroves.

13. Visit the 65-by-20 foot hurricane monument, constructed of locally quarried limestone, in memory of the over 420 people that died in the 1935 hurricane.

14. Stop by the History of Diving Museum to see a collection of vintage diving equipment and learn the story of undersea explorations and advancements.

15. DO bring sun hats, rash guards, and very powerful sun block. Some people’s children (ahem) got very sunburned.”

Come check out Anne’s Beach, various dining and hotel options, or other things to do in Islamorada and in Anne’s Beach.