Discover Florida’s 12 Best Islands: Explore Islamorada

Islamorada does an amazing job of blending a laid-back fishing lifestyle with island glamour.
Islamorada Sunrise

A fisherman heads out at dawn. (ANDY NEWMAN/FLORIDA KEYS NEWS BUREAU)

Islamorada does an amazing job of blending a laid-back fishing lifestyle with island glamour. On one hand, you can rise with the roosters and head to Bud N’ Mary’s Marina to spend the morning on the Florida Bay with a fishing guide. At 7 a.m. the waters are pleasantly placid, and the pink and mauve sky blends seamlessly into the bay as the fish start biting.

Or, you can leisurely awaken to a glorious sunrise over the Atlantic Ocean from the comfort of a king-sized bed at the chic Cheeca Lodge & Spa. Then spend the day relaxing on the shore or sipping your cosmo poolside in a Lilly Pulitzer swimsuit from the resort’s Signature Store.

Islamorada, a village of six islands, has a style of its own. The island’s moniker “Sportfishing Capital of the World” draws serious sports fishermen who come to compete in the Islamorada Sailfish Tournament. They want to battle a billfish and feel the saltwater crash into them as the mighty monster breaches the surface. For that experience, there are plenty of deep-sea fishing charters available. But the island also attracts those who prefer to simply fish off a bridge for snapper and snook, or kayak solo into the shallows to cast a line.

Besides fishing, Jet Ski tours take water babies to Cheeca Rocks, a national marine sanctuary with inshore patch reefs, to snorkel the Donut Hole, teeming with brain and finger corals, grouper and stingrays.

At the end of the day, it’s easy to unwind no matter what your style. Morada Bay’s Pierre’s Restaurant is an elegant choice. A path of tropical flowers leads to a two-story white estate house facing a palm-lined beach on the Florida Bay. Cocktails at the lounge’s rich mahogany bar and French-fusion cuisine in the dimly lit upstairs dining room add to the island’s romantic allure.

Meanwhile, the flip-flop crowd hangs at Lorelei, drinking margaritas out of plastic cups and munching on conch fritters. A local musician keeps them entertained with song as they watch the sun disappear into the horizon.

Islamorada also has its artsy side and a stop at the Rain Barrel Village, where the 30-foot-tall lobster sculpture Betsy greets shoppers, is a treat. Browse through stacks of watercolor prints and photos illustrating the Keys’ wildlife. Quirky lobster-trap wall décor and hand-painted buoys compete with more sophisticated metal wall art of fish and flora.

Don’t Miss…

History of Diving Museum

This impressive exhibition illustrates humanity’s obsession with the ocean. Diving bells from the 18th century, early scuba gear and more showcase the history of underwater exploration. Don’t miss the Treasure Room, where salvaging tools and recovered sunken treasures—a 16th-century iron chest and a 70-pound silver bar—are on display.

Robbie’s Marina

This is where the tarpon swim, waiting under Robbie’s dock for folks to come and feed them. At a nearby plywood shack you can buy fish food and hand-feed the silver kings splashing about. If you’re coming in from a day of fishing, the kitchen staff at the marina’s Hungry Tarpon restaurant will happily cook your catch.

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