Last Updated on December 20, 2023
If you are looking for the best things to do in Islamorada, you’ve come to the right place.
Long known as the “Sport Fishing Capital of the World,” the Village of Islamorada spreads across the beautiful, tropical isles of Plantation Key, Windley Key, Upper Matecumbe, Lower Matecumbe, and Tea Table Key.
It starts at Mile Marker 90.9 in the Upper Florida Keys.
Small Town Island Charmer
Pastel-painted shops, restaurants and resorts/marina greet you as you roll into town on the Overseas Highway.
Whether visitors come to fish for bonefish on the flats, snook in the backcountry, or mackerel out in the Gulf, the fishing is certainly world-class.
But Islamorada’s charms don’t end once you’re back on land.
In fact, some of the Florida Keys’ most entertaining roadside attractions and best museums can be found in this small Florida village, with a population of 6,600.
Robbie’s Marina
You can start the morning off right at Robbie’s Marina, a local institution on the bayside.
At Robbie’s restaurant, the Hungry Tarpon, enjoy breakfast with a view, while you also ponder which of the activities is most appealing.
Tourists love feeding the silvery tarpon from the dock. Beware of the pelicans. They can be pretty aggressive trying to get the fish away from the tarpons.
Others prefer to browse the stands of handicrafts and souvenirs. You may want to head out on a snorkeling trip or fishing charter.
The Hungry Tarpon Address: 77522 Overseas Hwy, Islamorada, FL 33036
Rent a Kayak
One of the most intriguing expeditions will necessitate renting a kayak from Robbie’s and taking a comfortable 20-minute paddle.
Kayaking gives you the chance to observe fish and birdlife up close, while you head out to Indian Key, a state historic site.
There you will pull your kayak ashore. You can walk through paths that have existed since the 1830s when wreckers lived here in a thriving town.
Stroll by foundations of buildings that once stood here, as you picture what life was like almost two centuries ago. Absorb the endless views of the sky and sea.
Florida Keys History & Discovery Center
After paddling back to Robbie’s Marina, you may want to head to the Florida Keys History & Discovery Center.
Here you can view exhibitions such as Legends of the Line – chronicling the extraordinary fishermen and women who became local legends.
Be sure to look at the Indian Key exhibit, which offers an excellent sense of how people once lived on that tiny 11-acre island in the 19th century.
The History & Discovery Center is located within the grounds of the Islander Resort, a family-friendly place to base your Islamorada stay.
The Islander boasts a (man-made) beach, restaurant, and large pool on the ocean side.
Their townhouses on the bayside are perfectly situated to watch the sunset. If you boat to the Keys, you’ll also find convenient dockage at the bayside property.
Florida Keys History & Discovery Center Address: 82100 Overseas Hwy, Islamorada, FL 33036
History of Diving Museum
For more history – of the underwater kind – cruise on over to the History of Diving Museum.
Even if you have never donned a mask and fins, this thoughtfully designed museum proves worth a visit.
From the early age of primitive diving equipment to incredible modern technology, the interactive exhibits and extensive collection tell a fascinating story of undersea exploration.
History of Diving Museum Address: 82990 Overseas Hwy, Islamorada, FL 33036
The Beach Café at Morada Bay
At lunchtime, consider the waterfront restaurant The Beach Café at Morada Bay. Some of Islamorada’s best bayside views can be appreciated here, with dining that is literally “toes in the sand.”
From classic conch fritters to mussels, crab cakes, and tuna tartar, this spot offers quality cuisine in a laid-back atmosphere.
It’s also a prime viewing spot to watch the sublime Florida Keys sunset.
The Beach Café at Morada Bay Address: 81600 Overseas Hwy, Islamorada, FL 33036
Theater of the Sea
Founded in 1946, Theater of the Sea is a classic attraction that appeals to children – and many adults, too. Its giant conch fountain out front is an Islamorada landmark.
Here you can enjoy entertaining and educational dolphin, sea lion, and parrot shows. The dolphins swim in a huge saltwater lagoon, carved out from limestone.
It’s also fun to take their small boat on a short lagoon excursion and watch dolphins race beside you.
Other exhibits at this aquatic park include sea turtles, sharks, and crocodiles.
With a wonderful “old Florida” charm, Theater of the Sea welcomes hundreds of repeat visitors every year.
Theater of the Sea Address: 84721 Overseas Hwy, Islamorada, FL 33036
Islamorada Art District
While the Village of Islamorada offers so many ocean-related activities, it is also becoming well-known throughout the Keys for its Morada Way Arts and Cultural District.
Several art galleries have also sprung up, featuring paintings, sculptures, and other hand-crafted objets d’art.
If you are fortunate enough to be in the village on the third Thursday of any given month, be sure to also check out the Art Walk.
This street festival spans the distance between the 1935 Hurricane Memorial and one of the Keys’ most beloved dining spots, the Green Turtle Inn.
With live music, performance artists, and artisans selling artwork and jewelry, the Morada Way Art Walk is a perfect way to round out an ideal Islamorada escape.
All photos are by Laura Albritton. Except for the dolphins at Theater of the Sea (by Steven Depolo, Flickr, CC BY 2.0). The Islander’s fishing pier (by Zickie Allgrove).
Fifth-generation Florida native Laura Albritton is the co-author of four books including Hidden History of the Florida Keys, published by The History Press.
With Keys historian Jerry Wilkinson, she has also written the books Marathon: the Middle Keys and Key West’s Duval Street.
Laura also produced a short film about the life Jerry Wilkinson. Check it out: Florida Keys Film Tells Heartwarming Story
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