Everything From Adventure and Fun in the Sun to Arts and Culture in Islamorada

Adventure and Fun in Islamorada

The Florida Keys represent different things to different people. Some immediately think of action-packed water sports at luxury resorts, while others picture frozen drinks. Still others imagine quiet beaches and slice after slice of Key lime pie. Each island in the Florida Keys has a specialty. But what if you want a bit of everything? Make it a priority to visit the island of Islamorada.

Wedged between the swampy wilderness of the Everglades National Park and the vast blue waters of the Florida Strait, you’ll find the sportfishing capital of the world. With access to desirable catches, an abundance of marinas, and tons of expert guides, it’s genuinely a fishing enthusiast’s paradise. But the vibrant art and restaurant scenes also leave plenty to attract the non-sportsman to Islamorada, as well.

kiteboarding in Islamorada



There’s perhaps no better—or more thrilling—way to see the landscape than by kiteboarding. Experience the water that defines this destination from an entirely different perspective. (Photo courtesy of oTHErside Boardsports)


The Florida Keys & Key West

With miles of beaches, an abundance of eclectic cultural riches, and communities known for welcoming, laidback attitudes, The Florida Keys & Key West invite you to “come as you are.” Enjoy tranquility and relaxation; fishing, diving, and boating; and top-tier dining, plus museums, artists and history, in island settings of stunning natural beauty.
Islands of Islamorada

Day 1Arrive in Islamorada

After driving from the Florida mainland along the Overseas Highway, check into the Islands of Islamorada in the afternoon. The resort is at mile marker 82.7, about an hour and a half drive from Miami.

Large groups and families might prefer one of the 22 waterfront villas with four bedrooms, full kitchens, and outdoor recreation space. There are also one-bedroom suites with ocean views.

Take some time to wander the property—maybe even stretch out on a beach chair or take a dip in the pool. Paddleboarding is also on offer if you’re ready to get in the sea.

Circle back to Marker 88, which you likely passed on your way to Islamorada, for dinner. The menu at this award-winning restaurant leans tropical, serving dishes like coconut shrimp with mango chutney, onion-crusted Mahi Mahi, and Florida lobster tail. After returning to the resort, make your way to the waterfront Ocean House bar for a nightcap.
Keys History and Discovery Center in Islamorada, FL

Day 2Enjoy The Keys’ Great Outdoors

Start the morning with a generous breakfast and maybe even a bloody mary or mimosa at Lorelei Restaurant. Dishes like shrimp and grits or biscuits and sausage gravy at this casual spot will fortify you for the active day ahead. Luckily, all the stops on today’s itinerary are near the resort, so you might have some time to go for a swim or hit the spa before your next activity.

Learn about the unique ecology and fascinating history of the Upper Keys at the Keys History and Discovery Center. Permanent exhibits cover topics like Henry Flagler’s Over-Sea Railway (which has since been transformed into the Overseas Highway) and Coral Reef Exploration. On the second floor, find a theater showing documentaries on topics like the 1935 Labor Day Hurricane.

Try kiteboarding during the daily afternoon session at Otherside Boardsports. Owners Mike and Shana Walsh are kiteboard instructors with plenty of experience teaching visitors how to ride a board over the water, propelled only by a kite catching the wind. The shop can arrange a suitable course if you’re a complete beginner; advanced riders who are 100 percent self-sufficient would likely prefer the option to book a boat trip.

You’ll surely work up an appetite during the afternoon watersports adventure. Fortunately, Islamorada Brewery & Distillery is located practically across the street. So for a casual dinner, claim one of the picnic tables, dig your toes into the sand, and sip on a cocktail or craft beer like the signature coconut Key lime ale. Then share an order of Spanky’s Special Fish Dip made from smoked local fish and orange habanero hot sauce or nachos with pineapple salsa.
Browse Morada Way Arts & Cultural District

Day 3Art for Art’s Sake

After a leisurely morning at the resort, grab lunch at Bad Boy Burrito and Bad Boy Sushi within the Village Square at the Trading Post shopping complex. The two businesses operate separately, but members of your group can order from both. The convenient set-up guarantees everyone will find something delicious, whether that’s vegan sushi rolls, Hawaiian-style poke bowls, or a burrito bursting with Key West pink shrimp and charred pineapple habanero salsa. While you’re here, take a peek at the stylish beachwear at Miss Monroe Boutique and handcrafted jewelry and home goods at Boo Kee Sue Botanics. There will be time to return later in the trip to check out these enticing shops more thoroughly.

For now, it’s time to browse Morada Way Arts & Cultural District. Small shops, galleries, and restaurants all come together to create this vibrant art district along a small stretch of the Overseas Highway. Each business is distinct: Gallery Morada displays works from nationally known artists; Pasta Pantaleo’s Signature Gallery is a tribute to his love of the natural world; and Morada Way Clay focuses on ceramics.

The final stop should be Florida Keys Brewing, the first microbrewery in the Keys. There’s always a rotating list of seasonal and barrel-aged beers available on draft, but you’d be remiss not to try the Iguana Bait, a light kolsch flavored with honey and hibiscus.

After a full day, it’s time for dinner at Chef Michael’s. Here, Chef Michael Ledwith has spent decades wowing diners with dishes that combine fresh Florida Keys ingredients with French techniques (the melt-in-your-mouth hogfish truly shines here). In keeping with its location just two blocks from Morada Way, the decor incorporates paintings and other works from local artists.
Islamorada is the sport fishing capital of the world

Day 4Go Fish

It would be fitting to spend the final day of your trip to Islamorada among fish at Robbie’s Islamorada, your one-stop shop for everything dedicated to the sport. The island is, after all, the sport fishing capital of the world.

If you’re hungry, there’s even a lengthy breakfast menu available at the marina restaurant, offering everything from yogurt and granola to frittatas and breakfast burritos. Or save your appetite for lunch—the menu is filled with Keys specialties like conch fritters, stone crab claws, and homemade Key lime pie. If you’ve had some fishing success, the restaurant will also cook your catch using the preparation method of your choice.

If you’ve been toying with the idea of experiencing Islamorada’s legendary fishing, now’s your chance. A whole slew of fishing boats that operate tours and charters dock at Robbie’s. Too much commitment? Then stick around the dock to feed the hungry tarpon. Robbie’s is famous for supplying buckets of bait (for a small fee) to visitors eager to feed the school of fish that congregate in the waters.

Visit The History of Diving Museum in the afternoon. The hands-on exhibits tell the millennia-long history of “man’s quest to explore under the sea,” allowing you to lift a silver bar from a sunken Spanish galleon in the treasure room. You’ll also leave with a better understanding of how diving technology has contributed to marine science, underwater photography, and treasure hunting.

Mark the last night of your trip to Islamorada with dinner on the veranda at Pierre’s Restaurant, an intimate eatery located on the top floor of a gorgeous house overlooking Florida Bay. The menu features local ingredients combined with global influences, like shrimp cocktail featuring Key West pink shrimp and a piquillo pepper sauce, seafood cassoulet made with a variety of local catches, and Florida lobster curry.

Shopping in Islamorada

Day 5Depart

After checking out at the hotel, return to Village Square at the Trading Post for a breakfast of French pastries and coffee at Café Moka. Now is also your chance to make any final purchases at the shops within the complex before departing for the Florida mainland.

The journey back to the airport provides the perfect opportunity to discuss the highlights of your trip to Islamorada. Whether your favorite activity was visiting the art galleries, the kiteboarding excursion, or simply relaxing by the pool, everyone is sure to return home with lasting memories that they’ll talk about for years to come.

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Journeys: United States
Journeys: Sports + Adventure