Islamorada bills itself as the “Sportfishing Capitol of the World,” and the fishing here is indeed among the best you’ll find anywhere, whether you’re chasing sailfish in the ocean or bonefish in the bay.
But that’s not all there is to this island village in the Upper Keys, a two-hour drive from Miami.
An interesting cluster of cultural attractions have been added to things to do in Islamorada: the Morada Way Arts and Cultural District, two fun craft breweries bursting with Keys flavor, a top-quality museum and historic walking tours.
Islamorada has terrific recreational opportunities, including a section of the Florida Keys Overseas Heritage Trail that provides scenic and safe bicycling, and my favorite kayak trip in the Keys — kayaking out to historic Indian Key.
Islamorada is also home to many classic Florida Keys hot spots and great places to eat and drink.
Here’s a guide to some of the best things to do in Islamorada, with an emphasis on the recent additions.
Two craft breweries now make their home in Islamorada
Exploring the Florida Keys means heat and sun, and two local breweries have opened in the last three years to quench the inevitable thirst of visitors.
The Florida Keys Brewing Company was the first craft brewery in the Upper Keys opening in 2015 and in 2018 it moved to a new taproom with a beer garden right off the Overseas Highway at MM 81.6 (81611 Overseas Highway.)
Its taproom is decorated in a colorful Keys-worthy way — with mosaics made from thousands of bottle caps from breweries worldwide. There are always a variety of locally brewed beers you can try as flights.
The brewery has a variety of programs scheduled including live music some nights.
We especially like the outdoor beer garden behind the buildings. There is usually a food truck present, so you can dine there too.
The other brewery, Islamorada Beer Company, 82229 Overseas Highway, is only blocks away and is popular with visitors who like trying flights of their 10 different drafts with names like Sandbar Sunday, No Wake Zone and Channel Marker IPA.
The brewery sells merchandise folks love to buy as souvenirs. In an adjoining space, the beer company has opened a rum distillery.
Things to do in Islamorada: The Morada Way Arts and Cultural District
The Morada Way district’s center is the historic 1935 Hurricane Monument and the iconic Green Turtle Inn nearby. The district stretches along the half-mile section of the Old Highway, which was the only road when the railroad ran down the middle of what is now the Overseas Highway.
An historic walking tour of Islamorada, available on the free smartphone app “Florida Stories” (Android and iOS), starts at the Green Turtle with tales of early pioneers, the most powerful hurricane to ever strike North America, Red Cross Houses built for survivors, the memorial built to honor the hundreds of victims, and one of the few bona fide pirate stories connected to the island chain.
The 10-stop, mile-long tour ends at the Pioneer Cemetery on the picturesque beach of the Cheeca Lodge, once the heart of this historic community.
Along with celebrating its rich history, Islamorada is working to recognize the many working artists and craftsmen who create a rich art scene. The Morada Way district is liveliest on the third Thursday each month, which features Art Walk with live music and performance artists.
The Florida Keys History & Discovery Center
Despite their small size and population, the Upper Keys are full of colorful history – from shipwrecks, hurricanes, pirates, and sunken treasure to vacationing movie stars. It’s where presidents go to fish, where classic movies have been filmed and where the Key Lime pie first became a must-have regional specialty.
The Florida Keys History & Discovery Center, 82100 Overseas Highway , Islamorada, is committed to telling those stories in an entertaining way. The museum opened in 2014 and is located on the grounds of the newly remodeled Islander Resort, 82100 Overseas Highway.
The Florida Keys History & Discovery Center is not like a lot of local history museums – small dusty rooms inside a public library.
It’s a two-story 7,500 square foot oceanfront museum with a state-of-the-art theater and exhibits designed by the same firm that did the interior of the Salvador Dali Museum in St. Petersburg.
The museum is blessed with a $1 lease for 50 years for its space inside the Florida Keys Conference Center on the grounds of the Islander.
With grants from the Monroe County Tourist Development Council and the help from the area’s pioneer families, the museum is collecting historic artifacts and completing its exhibits.
“People think Key West is where all the Florida Keys history happened, but what they don’t realize is the incredible amount of history in the Upper Keys,” said Brad Bertelli, the museum’s curator and historian. “There are so many untold stories.”
With the first floor devoted to permanent exhibits on topics like Indian Key, the original native American people, sunken treasure fleets and the tradition of sport fishermen, the museum’s upstairs houses changing exhibits and a 35-seat surround-sound theater.
The theater plays a loop of historic documentaries and interviews. In one, the oldest living survivor of the great Labor Day hurricane of 1935 is interviewed at age 101 about his experience during the storm that killed more than 400 and blew away Henry Flagler’s Over Sea Railway. It was the strongest hurricane to ever make landfall in the United States or Caribbean.
The Florida Keys Overseas Heritage Trail
A bike trail extends from Key Largo to Key West, but it’s not finished and some sections put cyclists next to highway traffic in a narrow shoulder.
In Islamorada, however, this trail takes the Old Highway and this section makes a delightful, scenic and safe 20-mile round trip.
Here are details about biking in Islamorada on the Florida Keys Overseas Heritage Trail.
Things to do in Islamorada: Feed the tarpon at Robbie’s Marina
I can’t drive down the Overseas Highway without stopping at Robbie’s Marina, bayside at Mile Marker 77.
The big draw at Robbie’s is the chance to see 50 to 100 enormous tarpon swimming around the dock in clear water only a few feet deep. Pay $2.50 to go out on the dock, and it’s another $5 for a bucket of fish pieces to toss to them.
It might be the most entertainment you’ll find in the Keys for a few bucks.
The tarpon splash and lunge; the pelicans try to steal the bait fish and the macho guys (sorry, it is always guys) try to hand-feed the tarpon at the risk of ending up with tarpon teeth up to their wrists.
While you’re there, the restaurant overlooking the marina, the Hungry Tarpon, is a long-time favorite.
It’s famous for its award-winning Trailer Trash Bloody Mary, made with house-infused cucumber vodka with bleu cheese, pickle, garlic olives, pickled green beans, crisp strip of bacon, celery, meat straw and a shrimp cocktail!
One of my favorite things to do in Islamorada: Kayak to Indian Key
One of those little green islands you see from the Overseas Highway is actually the former county seat of Dade County.
Now a ghost town, Indian Key is a state park accessible only by boat that preserves a community that thrived in the 1830s until an Indian attack in 1840 ended its development.
It’s a beautiful and fascinating place, and a perfect destination for kayaking through the shallow clear waters.
More about kayaking to Indian Key.
Take a glass-bottom boat tour of a coral reef
New to Islamorada at Robbie’s Marina in fall 2023, is glass-bottom boat tours aboard the new Transparensea glass-bottom boat.
Tours are offered day and night (with powerful lights!) of reefs such as nearby Alligator Reef. It’s a 46-foot boat that has a stabilizer to reduce motion. It can carry 49 passengers. Details: glassbottomtour.com.
Theater of the Sea: Historic marine mammal attraction
When Henry Flagler constructed the Overseas Highway, workers dug quarries into the coral rock to acquire building materials. In the 1940s, a tourist discovered a landlocked quarry on Windley Key, where rain had filled the quarry and somehow colorful parrot fish had thrived.
Eventually, the quarry was developed into Florida’s second marine mammal attraction — Theater of the Sea. (Marineland in St. Augustine was first.) It opened in 1946.
Today, the 17-acre attractions, which features lagoons, waterfalls, and tropical gardens, is home to a variety of animals including Atlantic bottlenose dolphins, California sea lions, sea turtles, sharks, rays, tropical and game fish, crocodilians and parrots.
There are several shows — dolphins, birds, seals and sharks each have their own. In recent years, the attraction has been popular for swim-with-the-dolphin and interact-with-the-sea-lion experiences.
Tripadvisor reviews generally say “expensive but worth it.”
Classic Keys tiki bars and restaurants in Islamorda
There is a very good choice of places to eat and drink in Islamorada — some people go primarily to eat, drink and sit by the water.
Here are a few favorites:
- The food is terrific, but the view is even better at one of our favorite restaurants, Lazy Days, 9867 Overseas Hwy, Islamorada, FL 33036. Located directly on the beach at MM 98 oceanside. it has a view of water that comes in a dozen shades of blue and the Alligator Reef Lighthouse in the distance four miles out.
- The Lorelei Cabana Bar and Restaurant, at Mile Marker 82 Bayside is a classic tiki bar: It has decks, chickee huts, palm trees and a sandy waterfront that create an expansive and outstanding place to watch the sunset. Hundreds gather nightly, lining the beach with cocktails in hand, to watch the sun sink below the horizon. It’s as pure a Florida Keys experience as you can have. Here’s a guide to the best Keys tiki bars, which includes Lorelei.
- Islamorada Fish Company, Islamorada at MM 81.5 is the original Islamorada Fish Company, which has now aligned itself with Bass Pro Shops with locations all over the country, including Fort Lauderdale. A popular seafood market is out front, and the restaurant and sunset tiki bar are out back, part of the neighboring Worldwide Sportsman, the temple of fishing owned by Bass Pro. The restaurant has its own fishing fleet, so the fish is fresh off the boat. A favorite: the clam chowder.
- Long popular at its location in Cudjoe Key in the Lower Keys, the Square Grouper has opened a restaurant in Islamorada that inspires the same sort of devotion. Located at MM 80.5 Gulfside, 80460 Overseas Highway, Islamorada.
- People like Mangrove Mike’s for breakfast and lunch. Recommended: lobster omelette. MM 82, Islamorada, FL 33036.
- The upscale and expensive white-tablecloth Chef Michael’s is known for outstanding food and a terrific key lime pie. It’s probably the highest rated restaurant in Islamorada. MM 81.7 Overseas Highway, Islamorada, FL 33036
Florida Rambler tip: Want to go fishing? Here are tips on how to hire a fishing charter in the Keys. An alternative to a charter: Hire a guide who’ll bring all the gear and help you fish from a bridge.
Two fascinating spots: A state park and a diving museum
Windley Key Fossil Reef Geological State Park: If you want to understand the Keys’ geological history, stop here to learn about the fossilized coral reef that underlies all of the Florida Keys.
The park is an old quarry for rock used in building Flagler’s Overseas Railroad in the early 1900s. Visitors walk along 8-foot-high quarry walls to see cross sections of the beautiful ancient coral – a sight you won’t find anywhere else.
You’ll also learn a lot on the self-guided trail through the native vegetation that identifies dozens of Florida Keys trees and bushes and how they have been used.
Windley Key Fossil Reef Geological State Park
84900 Overseas Highway
Islamorada FL 33036
History of Diving Museum: About 15 years ago, Joe and Sally Bauer, both physicians, opened this museum to display their collection — one of the world’s largest — of diving helmets, hand-operated air pumps, armored suits, lights and other memorabilia and media about diving. Visitors describe it as fascinating, even for non-divers,
History of Diving Museum
82990 Overseas Highway
Islamorada, FL 33036
Three free things to do in Islamorada
- Pack a picnic and spend the day at Anne’s Beach, at mile marker 73.5. Here’s a Florida Rambler story on Anne’s Beach, a free natural sand beach with several picnic pavilions set in the mangroves along a boardwalk.
- Browse through the the World Wide Sportsman. My friends calls it “The Temple of Fishing,” where a replica of Ernest Hemingway’s wooden fishing boat, the “Pilar,” is on display on the main sales floor. Just a three-minute walk from the Morada Way arts district, World Wide Sportsman, which is owned by the Bass Pro Shops chain, carries a comprehensive line of fishing tackle, clothing and accessories to outfit even the most experienced fisher. The World Wide Sportsman complex is next door to the Islamorada Fish Company.
- Have your picture taken with Betsy the Lobster outside Rain Barrel Artisan’s Village, a fun spot to browse the arts and crafts booths. Everybody has to get their picture taken with Betsy, an anatomically correct Florida lobster that is 30 feet high and 40 feet long. Betsy created by Marathon artist Richard Blaze three decades ago.
Resources for things to do on a Florida Keys vacation:
- Mile Marker Guide with dozens of stops to help make the most of your drive south.
- The Florida Keys Overseas Heritage Trail. Florida Rambler report
- Florida Keys wildlife: Places to see animals
- Tiki bars you’ll love in the Florida Keys
- 11 great kayak outings in the Keys
- Free beaches in the Florida Keys
- Original African Queen boat in Key Largo
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The author, Bonnie Gross, travels with her husband David Blasco, discovering off-the-beaten path places to hike, kayak, bike, swim and explore. Florida Rambler was founded in 2010 by Bonnie and fellow journalist Bob Rountree, two long-time Florida residents who have spent decades exploring the Florida outdoors. Their articles have been published in the Sun Sentinel, the Miami Herald, the Orlando Sentinel, The Guardian and Visit Florida.