Explore the Best Things to Do in Islamorada, Florida

Vacations in the Florida Keys are as spectacular as ever. Florida’s southernmost tip is home to hundreds of uninhabited islands connected to the mainland by the 113-mile Overseas Highway. While the complete trip from Key Largo to Key West is a bucket-list trip worth considering, Islamorada is perfect for a long weekend.

The beautiful seaside community has six islands between Key Largo and Key West. As the Sportfishing Capital of the World, there’s more to do than stare into the turquoise expanse, but the blue-green sea makes it easy. Islamorada is the place to go for beach-inspired art, snorkeling, and pina coladas while watching the best sunset of your life. The top 20 Islamorada, Florida attractions are listed below.

Visit the Diving History Museum

The History of Diving Museum can answer your burning questions about the underwater environment. Since 2005, the museum has housed one of the world’s greatest collections of diving helmets, air pumps, and armored suits.

Visit Florida Keys History & Discovery Center

This local history museum covers Florida Keys’s history from its early residents to today. Exhibits cover everything from the Oversea Railway to the Keys’ amazing coral reef system.

Explore Windley Key Fossil Reef Geological State Park Trails

Explore the Best Things to Do in Islamorada, Florida

Explore a conserved quarry that produced Keystone and the Overseas Railroad. Windley Key trails lead through hardwood hammock trees and reveal ancient coral in 8-foot quarry walls. Education about the historic place is available at the visitor’s center.

Enter Indian Key Historic State Park

Dade County’s county seat located on this little island accessible only by kayak. Today, paddle right up to shore (Robbie’s Marina or Backcountry Cowboys rents) and relax by hiking, swimming, and sunbathing.

Bring the Family to Founders Park

The perfect family park is 45 acres. A shallow-water swimming area on the Florida Bay, grills, pavilions, picnic tables, and tiki huts provide all you need for a perfect beach day. Other park facilities include an Olympic-sized pool, splash pad, and sports fields.

Theater of the Sea Dolphin Swim

Explore the Best Things to Do in Islamorada, Florida

It’s easy to get close to water life in Islamorada, but swimming with dolphins may require more preparation. Theater of the Sea marine mammal park entry includes dolphin, sea lion, and parrot presentations, a bottomless boat ride, fish and reptile tour, and a lagoon-style beach. An unforgettable dolphin swim is available.

Visit Islamorada’s Robbie’s Marina

This Florida Keys landmark is a paradise for island enjoyment. Feed the enormous tarpon off the docks, ride Captain Michael’s party fishing boat, or snorkel. Hungry Tarpon Restaurant offers a sunup-to-sundown view of the water for landlubbers.

See Rain Barrel Village

Rain Barrel Village, another Keys landmark, has drawn visitors for 40 years to see Betsy the Lobster, stroll through gorgeous gardens, and buy local art. Walking through this tropical haven’ bright galleries and outdoor stores puts you on island time. Live music and beverages at the onsite bar enhance the festivities.

Walk Morada Way Arts & Cultural District

Explore the Best Things to Do in Islamorada, Florida

Morada Way is the Florida Keys’ downtown or main thoroughfare for six blocks. The vibrant quarter has scores of galleries, cafés, studios, and stores surrounded by parks and bike routes. Wander around stores to find unique items throughout the afternoon.

Break for Coffee

The colorful Midway Café and Coffee Bar is a famous Islamorada breakfast spot. Besides breakfast, you can buy from their extensive pastry case and specialty coffee and tea drinks like Almond Joy (coconut, chocolate, almond latte) or Banana Chai Frappe.

Enjoy Real Mexican Food

Bad Boy Burrito makes the best overstuffed burritos anywhere. Choose from five homemade sauces, Key West pink shrimp, pork carnitas, or local fish, and all the toppings. One of the best brunches in town.

Try Craft Beer

Is there anything better than a cold beer on a hot day? The Sandbar Sunday, Islamorada Beer Company produced an American Wheat Ale for boating days. Come to the Islamorada brewery bar for a pint or a flight of delightful beers like the Keylime Hibiscus Ale or Floridays Tropical Pale Ale.


Vacationing in the Florida Keys, particularly Islamorada, offers a spectacular retreat. With its rich history, diverse marine life, and vibrant cultural scene, Islamorada provides a perfect long weekend getaway. From exploring museums and parks to enjoying local cuisine and craft beers, the top attractions ensure an unforgettable experience in this tropical paradise.


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