Start from 30 curated places around Islamorada, FL, then choose the recommendations that fit your guests.
Restaurants & cafés
Wahoo's Bar and Grill
Perched above Whale Harbor Marina at mile marker 83.4 with a panoramic deck over the Atlantic, Wahoo's has been voted the top restaurant in Islamorada by visiting diners and locals alike. The menu pulls from what the charter fleet brings in daily: wahoo, grouper, mahi, and stone crab in season. It's a straightforward, genuinely fresh operation that doesn't need to oversell itself.
Chef Michael's
A small, polished dinner room on Upper Matecumbe with a menu built entirely around what the local boats brought in — hogfish, triple tail, lionfish, ceviche in a coconut half. The kitchen rotates the whole menu around availability, which means the food is as fresh as Islamorada gets in a real sit-down setting. Reserve ahead; the dining room fills nightly.
Trails & outdoors
Anne's Beach
A half-mile elevated boardwalk on Lower Matecumbe that winds through a coastal wetland hammock to a narrow beach on the Atlantic side, with covered picnic tables and clear views across the shallows. It's the most accessible nature walk in Islamorada — flat, short, and free — and consistently rewards a slow morning with shorebirds, crabs, and the kind of quiet that the resort beaches never have.
Windley Key Fossil Reef Geological State Park Trails
Two short trails inside the old coral-rock quarry — the shaded Hammock Trail through a tropical hardwood forest and the Windley Trail through the quarry cuts — that together give a rare ground-level view of the ancient reef formation. The cuts are 10 to 15 feet deep in places, with fossilized coral brain and elk patterns exposed at eye level. A single entrance fee covers both loops.
Things to do
Robbie's of Islamorada
The single most irreplaceable stop in Islamorada: a sprawling open-air marina at mile marker 77.5 where more than 100 prehistoric-looking tarpon — some six feet long — congregate daily for hand-feeding off the dock. Beyond the tarpon, Robbie's operates snorkel trips to Alligator Reef, kayak rentals for the Indian Key and Lignumvitae Key routes, and a bait market with a waterfront restaurant. It is loud, alive, and genuinely memorable.
Theater of the Sea
A family-owned marine attraction open since the 1940s at mile marker 84.7, with dolphin and sea-lion shows, a stingray touch pool, shark swims, and rescued sea turtle encounters in lagoon-side enclosures fed by natural sea water. It's smaller and more hands-on than the big commercial parks, and the animal care program is oriented around rescue and education. Best for families with kids who want more than a beach day.
Landmarks & sights
Florida Keys Memorial
A WPA-era coral-rock monument at mile marker 82 that honors the hundreds of World War I veterans and local residents killed in the 1935 Labor Day Hurricane, then the most intense Atlantic hurricane on record. A ceramic-tile mural of the Keys covers a stone crypt holding victims' remains. It sits quietly beside the highway, easy to miss but deeply moving once you stop.
History of Diving Museum
Thirteen galleries tracing 4,000 years of human underwater exploration, housing one of the world's largest collections of international diving helmets, vintage scuba gear, and naval equipment. The submarine and helmets from the film 20,000 Leagues Under the Sea anchor a collection that feels genuinely curatorial, not kitsch. Best for a focused hour of history well off the beach.