6 fabulous things to do in Islamorada, Florida

While Islamorada has just 7000 residents on its 7-mile-long land mass, the artistic flair and natural beauty of this gem in the Florida Keys make it feel 10 times bigger.

In the Sportfishing Capital of the World, both weekend amateurs from South Florida and competitive fishers seek trophy catches in the open blue-green waters. But there’s more to Islamorada than fishing, one of the Keys’ top activities.

Shallow flats and the dense mangroves create vistas of lush natural beauty. History buffs know that this was the site of a 16th-century Spanish fleet wreck, making for fascinating coastal dives. Art lovers linger in quaint galleries and studios featuring beachy work. And if you’re in search of that famous Keys quirkiness, you can’t miss Betsy: a 30ft-high, 40ft-long recreation of a Florida spiny lobster.

Read on for the best things to do in Islamorada in the Florida Keys.

1. Feed some very, very big fish at Robbie’s Marina

Islamorada’s scruffy jewel, Robbie’s Marina covers all the bases. It’s a local flea market, tacky tourist shop, sea pen for tarpons (massive fish), waterfront restaurant and jumping-­off point for fishing expeditions – all wrapped into one irresistible, driftwood-laced compound. Boat rentals and tours are also available.

When you park, you’ll first be confronted with the market part of Robbie’s, where art and crafts from around the Keys make for unique souvenirs. If folks aren’t perusing paintings, they might be knocking back beers while checking out the waterfront view. Yet most come here for one thing: to watch and feed the freakishly large tarpons from the dock. Watching, in this case, isn’t just looking down at the thrashing creatures but also observing the visitors' shock when a fish the size of a large dog comes snapping out of the water.

Planning tip: While nearly everyone arrives in Islamorada by car, it’s easy to get around the island by bike once you’re here. Twenty miles of the Florida Keys Overseas Heritage Trail runs through the village, making for a flat, paved path through much of town. Rent wheels at Backcountry Cowboy Outfitters.

2. Rent a kayak to reach two state parks

If you find the onshore scene at Robbie’s a lot, you can quickly escape the bustle by renting a kayak for a peaceful paddle through nearby mangroves, hammock (dense forest) and lagoons. In fact, this is the major launching point for paddlers who are looking to get out to Indian Key and Lignumvitae Key – both state parks and both only accessible by boat.

Now lonely and eerie, Indian Key was once a thriving town, complete with a warehouse, docks, streets, a hotel and about 40 to 50 permanent residents. (It was actually the first seat of Dade County, now dominated by metro Miami.) Lignumvitae Key is a 280-acre island of virgin tropical forest ringed by alluring waters. The official attraction is the 1919 Matheson home, with its windmill and cistern; the real draw is a rare sense of shipwrecked isolation. Strangler figs, mastic, gumbo-limbo, poisonwood and lignum vitae trees form a dark canopy that feels more South Pacific than South Florida.

Detour: If you don’t want to paddle yourself, book a boat tour to Alligator Reef Lighthouse, a decommissioned lighthouse bearing the name of a pirate ship that sank 100 years ago. The waters around the beacon are crystal clear and marine life dances below, making for a prime snorkeling spot.

3. Take in Islamorada’s creative side

Islamorada’s colorful surroundings have attracted a vibrant community of artists who draw inspiration from the striking natural surroundings. Oil painter Taylor Hale and his wife, Kelly, own the Hale Gallery, just north of the Overseas Hwy. The space features an ever-rotating selection of local artists in addition to hosting events ranging from flow yoga to sound healing and Reiki group meditation.

Just south of the gallery is another hub of creativity. A spirited six-block stretch, the Morada Way Arts and Cultural District brims with galleries, working studios and even a Little Free Library tucked down a side street. Every month, the organization hosts an Art Walk that brings the area to life with live music, vendors and plenty of artistry.

Local tip: Fans of live music should head to Lorelei for a laid-back vibe and oceanfront views. (You may even catch a peek of the Nautilimo, a pink ocean-going Cadillac, in the neighboring marina.) The two biggest breweries in town, Islamorada Brewery & Distillery and Florida Keys Brewing Co., regularly have live music in their appealing backyards.

4. Order the Keys’ signature cocktail at the Tiki Bar

The Rum Runner is the signature cocktail of the Florida Keys. Consider it a tropical garden in a glass: pineapple juice, orange juice, banana juice, grenadine and lots of rum. The drink was invented at Islamorada’s Holiday Isle Tiki Bar, supposedly as a means of getting rid of excess rum before a new shipment of liquor arrived. (The recipe certainly succeeded in that goal.) Holiday Isle is now the Three Waters Resort, and visitors are still welcome at the Tiki Bar, a lovely establishment where you can feel the sand squish beneath your toes. Which is about as much physical activity as we can recommend after a Rum Runner or two.

Planning tip: After happy hour, refuel at Lazy Days, where you can take your pick of award-winning seafood with ocean-view dining – tables are set up in the sand, on the patio and indoors.

5. Get a glimpse of local geology at Windley Key

To build a railroad across the islands, Gilded Age mogul Henry Flagler had to quarry out sizable chunks of the Keys. The best evidence of those efforts can be seen at a former quarry turned state park: Windley Key Fossil Reef Geological State Park. Windley Key has leftover quarry machinery scattered along an 8ft quarry wall that reveals fossilized evidence of brain, star and finger coral embedded in the rock. The wall offers a neat (and rare) peek at the coral that forms the layer under the Keys: the cake layers of fossilized shells known as Key Largo limestone, or simply keystone.

Several short trails through tropical hardwood hammock make for a pleasant glimpse into the Keys’ wilder side – birds love it here. Borrow a free trail guide from the visitors center to take it all in.

Detour: If you’re less interested in history and nature and more interested in lounging in the sun, head to Anne’s Beach, a family-friendly beach with calm shallow waters, pavilions, a boardwalk and restrooms.

6. Snap a photo of Betsy the Lobster

One of the Keys’ most unusual roadside attractions is a monumental sculpture of a Florida spiny lobster dubbed Betsy. The giant crustacean is settled around mile marker 86, just outside Rain Barrel Village. Sculpted by Richard Blaze in the early 1980s, Betsy salutes the significance of the spiny lobster in the Keys’ commercial fishing industry and food scene, and also serves as a symbol of the importance of the broader wildlife found throughout the Keys. Stop in front of the piece and snap an unforgettable photo, then wander the gardens and peruse one-of-a-kind items from local artisans.

Planning tip: A local standby, M.E.A.T. Eatery and Taproom has can’t-miss burgers and a craft beer selection from near and far.

This article was adapted from Lonely Planet’s Miami & the Keys guide, published in August 2025.