Islamorada, Florida -- the place where the Upper Keys begin their rustic resplendence and any hint of cosmopolitan transitions to quirky. Coconut palms seem to sway a little more sensually in the tropical breezes. The clear, inviting shallow saltwater sparkles, reflecting a brilliant blueish green. Key Largo may be the first of the islands in the famous coral cay archipelago stretching south-southwest to Key West – and it has many attractions and important businesses and suburban communities – but Islamorada is where island time begins in earnest.
I wrote about this incredible destination in the Florida Keys for a USA Today special magazine, the Go Escape (Winter) 2023 edition. As always, many photos sent for consideration aren't published, so here at outdoorsrambler.com we can share all the beautiful images that didn't make the print magazine, along with additional tidbits of information about this idyllic piece of paradise.
If you want to fish, hang out, listen to live music while you're eating or enjoying drinks (outdoors when weather permits), Islamorada has it all. Of course, you can drive an extra couple hours (about 72 miles) to Key West, but if you're simply seeking an island vibe with that clear blue water and abundant sunshine, you really don't need to head further down the archipelago.
Here's a look at how you, too, can enjoy boundless fun in Islamorada, with photos at some of the eat, stay, experience options.
Stay:
Here's a little confession. While the bulk of our story takes place in Islamorada, we did stay for an afternoon and evening at the southern end of Key Largo, just a short distance before crossing the bridge into Islamorada. The Kona Kai Resort was highly and deservedly recommended, a boutique place where individual units are arrayed on beautiful grounds with an incredible waterfront setting. It was comfortable, quiet and the waterfront was stellar. The managers let us pick all the ripe star fruit we wanted from a tree on the property and even had some tips for adding it to wine and other beverages.
The Florida Keys are a seafood lover's delight. I tend to try the fresh, whole grilled or fried fish often spiced up with some sort of Caribbean-style seasonings. Many of the restaurants, such as Sal's Ballyhoo's, which was almost directly across the highway from Kona Kai, have a "hole-in-the-wall" feel to them. I always try to check out these smaller venues as well as larger, more heavily promoted options. More on dining later...
The main part of the trip was based out of Casa Morada, a 16-unit boutique, European-styled property. It's lush and tropical, with extensive trees and vegetation lining sandy paths between the two main buildings and the waterfront featuring a small bar, freshwater pool, saltwater lagoon and gorgeous views across Florida Bay. Each comfortable suite is unique.
A stay at pet-friendly Casa Morada includes complementary use of bicycles, paddleboards and kayaks. Yoga classes, private bay and sunset sails are available at the property. While many larger resort properties post myriad, “Thou shalt not,” prohibitions, Casa Morada’s main limitation is that it is for adults only. Management respects and understands the appeal to a certain class of visitor, such as those ones who might enjoy a fine cigar with a favorite spirit while lounging on the small patios in front of each unit.
The place is quiet, well off the Overseas Highway. Manager Hazel Thompson says visitors love the property’s tranquil, serene getaway potential. “A lot of people desire to retreat from their ordinarily busy lives, to decompress,” she said. “We offer that, create that pullback.”
Eat and Drink
If fresh seafood and sandwiches with ample, tasty sides paired with local brews or well-mixed drinks is appealing, you’ll find abundant options. I asked Stephanie Kinlaw Burns, a local bartender who has worked at multiple Islamorada restaurants, including the waterfront bar at Casa Morada, for her suggestions. She says most menus offer elevated pub grub, although you can find steaks among the abundant burgers, tacos and seafood. Lazy Days and Square Grouper have exceptional fish sandwiches, she said.
Fishing guide Matt Bellinger of Bamboo Charters at the Worldwide Sportsman Bayside Marina offered that Square Grouper affords the best panoramic sunset views, from its third-floor vantage point. Burns says most sunset views in Islamorada are similar; it’s just a question of avoiding obstructions, mangrove islands or other features that impact your view as the orange disc sinks into the western horizon.
“Off-the-beaten path is a challenge these days,” he said, “but I recommend Captain Craig’s, on Plantation Key. They didn’t originate fish sandwiches, but as Craig used to say, they perfected them. It was always our restaurant for the little neighborhood where I live.”
He also recommends Meza Morada, a Mediterranean kitchen with dips, salads, baba ghanoush and other fun stuff. “Fresh food made daily. A vegetarian or pescatarian would love it,” he said. Another good place for an inexpensive breakfast or lunch is the Marathon Bagel Company, a spinoff store from marathon Key, just opened on Plantation Key. “Homemade New York style deli bagels with sassy, playful counter service,” Bellinger added.
Whale Harbor’s Wahoo Bar and Grill also offers impeccably blackened grouper or mahi sandwiches. Wash them down with an ice-cold, eminently quaffable “Go Fish” lager, created by Bellinger in partnership with Islamorada Brewing Company. Bellinger calls it, “that craft beer for us old guys who don’t want too IPA hoppy or stout. It’s a great on-the-water brew.” It was nearly 100 degrees the day we fished. The cold brew went down easily and quickly.
Marker 88 is an iconic Islamorada dining destination. Almost everything in the Keys identifies by mile marker. It has undergone recent, extensive renovation. Dining when we were there last year was limited to outdoor seating, but the options were many with beachfront decks with table umbrellas near the live music stage and a covered, expansive pavilion. The Key Lime Seafood, featuring shrimp, lobster, crab and Tabasco butter over cilantro-lime rice was amazing, as was the blackened mahi fajitas, served with an array of toppings, although once you taste the mint chutney there’s no need to sample further. The bar offerings, including a pineapple coconut margarita, were superb.
Pina colada fans will love the handmade concoction at Oceanside Safari Restaurant. It was certainly one (okay, I had two) of the best I've ever tasted, with luscious cream of coconut, top-shelf rum and flawless blending. The food there, including tender, fried coconut shrimp hit the spot.
Anglers who keep their catch can try one of the many “hook and cook” dining options, places that will take your fresh fish and cook it for you, often in a couple of assorted styles and side dishes. “The Keys are famous for this,” Bellinger said, “and Islamorada Fish Company at the Worldwide Sportsman store is a wonderful place to have it. You’re sitting right on the water with a perfect bar that overlooks the marina. You can come by boat. Sit around and have a drink with the fishing guides, get some tips and hints.”
Live music abounds in the Keys. A destination venue in Islamorada is the Lorelei Restaurant and Cabana Bar. It sets the standard when it comes to performing acts, featuring full bands, duos and solo acts on guitar. Groups are sometimes booked from Miami or other large music scenes. Food, drink, music, scenery – there’s a lot to like at Lorelei.
More intimate is the Florida Keys Brewing Co., which features live music daily, often in the compact, shaded beer garden outside the taproom. Co-owner Cheryl McBay is a third generation Floridian, born and raised in Islamorada. She designs all promotional material and labels for the beers. Her husband Craig, Canadian by birth, is the brew master. They opened in 2014 and rapidly scaled up, now distributing across much of Florida. The fan favorite is Iguana Bait, a honey/hibiscus Kolsch, with the honey locally sourced in the Keys. Other top picks include Spearfish Amber and Spiny Hopster, a hazy IPA. Smelly Butt Pineapple IPA is a local fave, named for how people sniff a pineapple to assess ripeness. They also use a lot of tropical fruits in their beers – mangos, starfruit and passion fruit bought from farms near Homestead in south Florida.
“It’s a happening place,” McBay said. “I wanted a good live music venue. We actually had Billy Strings here two years ago.” Another cool partnership sees the Taco Jalisco food parked adjacent to the taproom and open six days a week. Customers can order fresh, authentic tacos, bring them into the bar or outdoor beer garden and pair it with a drink. “Locals live off that taco truck,” McBay said.
Here Fishy, Fishy!
Islamorada has several marinas catering to saltwater anglers. Marinas, guiding services and lodges devoted to fishing enthusiasts began flourishing in the early-to-mid 20th Century as anglers invested time and treasure to tangle with huge tarpon, permit and bonefish, plus a host of other sporting species. Islamorada’s Bud N’ Mary’s Marina dates to 1944. Several other marinas, like Whale Harbor, offer exceptional fishing, views and food with onsite restaurants and bars.
Bellinger has guided in the Keys’ “backcountry” for 34 years. The area spans Florida Bay and its many tiny coral islands and reaches into the southernmost waters of Everglades National Park. "March to May is fantastic fishing,” Bellinger said. “You still have cool weather and in the blue water offshore, you’ve got sailfish, blackfin tuna and mahi. The reef has mangrove snappers and yellowtails. The backcountry offers tarpon, snook, redfish, permit, bonefish, speckled trout and all sorts of snapper. There’s even Spanish mackerel and cobia. Depending on the kind of fishing you’re seeking, you can really change things up, mixing a variety of styles and species in one day.”
While Islamorada is known as a destination for resolute anglers, family fishing opportunities abound. Most marinas offer affordable party boat excursions to the Islamorada Reef, where even inexperienced anglers can usually get various snapper, rainbow runners, or other reef species to bite. Big fish also come cruising through. We went on the party fishing boat out of Robbie's, at the southernmost end of Islamorada. The boat had a diverse mix of anglers aboard, including a newlywed couple from Manitoba, Canada, and a family from Indiana. Everyone had fun watching fish come up from the reef as chum was introduced into the water. Several snapper came home with me, destined to be cooked on an asado grill while being basted in an array of tantalizing enhancements. You can see how we cooked these fish on this video filmed at Asado Life in St. Augustine, Florida.
Speaking of Robbie’s, no trip to Islamorada is complete without a trip to feed the tarpon. These massive silver kings prowl the dock area and adults and children alike revel in kneeling or laying down and dangling a menhaden forage fish over the water to entice the toothless monsters to rise and snatch it away. Robbie’s has a little of everything: a bar, restaurant, some gift shops, and outdoor activities including party boat fishing at the Islamorada reef, snorkeling and parasailing. Naturally, seafood dishes star in the Hungry Tarpon restaurant, but after feeding a six-foot fish by hand, settling in and sipping a loaded Trailer Trash Bloody Mary just might be in order.
Jet Skis, Diving, History
If you want to get on the water in a little sportier fashion, go on a jet ski tour - many locations rent personal watercraft or you can sin up for a tour with some instruction, as I did with Spray Watersports at Pelican Cove Resort.
They offer rentals and guided trips year-round. “The 90-minute tour is the way to go,” said guide David White. “You get up close and personal with the mangroves, see wildlife, visit islands." We traveled 26 miles on our tour and often include a stop at the Islamorada sandbar, a major party destination for boaters and sun worshipers. White said jet skiers in the winter months often wear neoprene to ward off the chillier water spray, sometimes dipping to around 70 degrees. Warmer months simply require a bathing suit.
Our expedition was exhilarating, with the machines sometimes zipping along the calm waters at nearly 50 miles per hour. One family immediately booked a trip for the next day as soon as they climbed off the machines back at the resort.
The History of Diving Museum is right off the main road. This Islamorada museum features thousands of artifacts gathered over 40, including one of the world’s largest collections of diving helmets, hand-operated air pumps, armored suits, lights and other accessory gear, plus memorabilia, prints, photographs, books, film and video. It traces the history of diving from centuries ago to the modern era, featuring military, commercial and recreational diving, including treasure hunters. It's a destination stop for divers from around the world and is said to have one of the largest collections in the world.
The Florida Keys History and Discovery Center is well-designed and located on the property of the Islander Resort. The two-floor center includes films, permanent and rotating exhibits. Among them: Keys First People, examining the several tribes of indigenous people who first settled the area; the 1733 Spanish Fleet, which focuses on the treasure fleet that largely perished in a September hurricane off the coast of the Upper Keys; Stories of the Upper Keys, an interactive, elaborate exhibit detailing significant events such as the building of Henry Flagler’s Over-Sea Railway, the Overseas Highway, and the 1935 Labor Day Hurricane, and video interview with President Herbert Hoover after a fishing excursion from North Key Largo’s exclusive Angler’s Club; and Legends of the Line, which explores the legendary fishing guides and fishermen who frequented the Upper Keys from 1915 through the 1960s and beyond. Fishing helped shape the Keys major industry – tourism.
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