17 Cool Things to Do in Islamorada On Your Florida Keys Getaway

Planning a trip to the Florida Keys? Spice up your journey by exploring all the best things to do in Islamorada, Florida. Known as the sport fishing capital of the world, Islamorada has endless opportunities for fishing, swimming, snorkeling, and scuba diving.

Visiting the “gem of Florida” gives visitors the chance to swim in some of Florida’s clearest waters and learn about the state’s rich history through many national monuments and state parks. In downtown Islamorada, you’ll find many local brewing companies and exceptional restaurants with outdoor seating. 

Need help finding what to do in one of the Florida Keys’ top destinations? Plan your ultimate trip with this complete guide to the best places in Islamorada, FL!

Why Treksplorer? Founded in 2011 by Ryan O’Rourke, Treksplorer provides travel recommendations and advice to millions of readers every year. Our content is rooted in our writers’ firsthand experiences, in-depth research, and/or collaborations with other experts and locals. Read more about our editorial policy.

Theater of the Sea

If you’re trying to see Islamorada in one day, Theater of the Sea needs to be on your to-do list. Established in 1946, this marine mammal park has interactive exhibits where you can see dolphins, California sea lions, stingrays, and nurse sharks.

Theater of the Sea

The Theater of the Sea’s tropical gardens let you get up close and personal to some of Florida’s natural wildlife. The general ticket admission lets you see the gardens and marine life. You can also make reservations to swim with dolphins, meet sea turtles, or swim with sharks.

Once you’ve finished all your animal encounters, relax at the lagoon-side beach. 

Florida Keys History and Discovery Center

No trip to Islamorada is complete without visiting the Florida Keys History and Discovery Center. At this 7,500-square foot oceanfront museum, you can learn about the colorful history of the Florida Keys and the settlements that started the state’s history.

The Florida Keys History & Discovery Center is loaded with permanent exhibits, as well as rotating exhibits featuring local work or recently discovered items.

Spend the day learning about Florida’s native people, the pirates and salvagers that destroyed the peninsula, and the Spanish Treasure Fleets that came looking for gold and stones. You can also learn about the underwater world in the Coral Reef Exploration Exhibit.

Anne’s Beach

Looking for one of the finest beaches in the Florida Keys? Swoosh over to Anne’s Beach. Visitors drive from far and wide to check out this seaside paradise, as it’s one of the only natural sand beaches in the Florida Keys.

Anne's Beach

Named after the local environmentalist Anne Eaton, this beautiful beach is located at mile marker 73.5 in Islamorada. With a picturesque boardwalk and stunning mangroves, Anne’s Beach is a breathtaking place to go for a swim or build sandcastles with the kids. It’s easily one of the loveliest beaches in Islamorada.

Make sure to pack for a picnic. There are 6 different pavilions for picnic tables at Anne’s Beach, giving you and your family ample places to relax and eat together.

Although the beach is stunning, the water is very shallow. You can sit in the water and read a book, but it’s not an ideal spot for swimming.

History of Diving Museum

Love diving or always dreaming of learning how to scuba dive? The History of Diving Museum is an educational institution dedicated to showcasing how diving is a fantastic way to understand and explore the sea. South Florida and the Florida Keys have played an essential role worldwide in the exploration of the ocean.

The History of Diving Museum holds the world’s largest collection of historic diving equipment and research documents. You can also see how scuba diving helmets and equipment have evolved over the years to make diving safer and easier. 

After your tour of the museum, don’t skip buying unique souvenirs at the gift shop.

Indian Key Historic State Park

For the ultimate adventure near Islamorada, head to Indian Key Historic State Park. One of the must-see state parks in the Florida Keys, it’s only accessible by kayak. Most kayakers launch their kayak adventures from Indian Key Fill in Islamorada. 

Indian Key Historic State Park

Even though the state park was once home to a Native American tribe, the tiny island is now considered an uninhabited ghost town. The water and land are absolutely stunning and well-preserved since it doesn’t have any residents or many visitors.

Bring your hiking shoes and a swimming suit to get the most out of your visit to Indian Key Historic State Park. You can also rent paddleboards or snorkeling equipment for your trip. If you have a fishing license, the small pier is a fantastic place to try your hand at catching dinner.

Morada Way Arts and Cultural District

If you’re venturing to downtown Islamorada, the Morada Way Arts and Cultural District is always alive and bustling. If you happen to be in the Florida Keys on the third Thursday of the month, you can visit the district during its monthly Art Walk. The walk features late-night gallery showings, live music, unique food sampling, and drink specials.

The few blocks of the arts & cultural district run parallel to the Overseas Highway between mile markers 81 and 82. The neighborhood has partnered with Chef Michael’s, a popular restaurant that makes all their specialty dishes with locally sourced and fresh ingredients. Fresh seafood is also available from a number of nearby food vendors, including Kaiyo Grill & Sushi and the Green Turtle Inn

Even though the Morada Way Arts and Cultural District sprawls over just a few blocks, make sure to strap on your walking shoes to explore all its art galleries and food vendors. 

Windley Key Fossil Reef Geological State Park

Looking to explore another large coral reef and go hiking? Windley Key Fossil Reef Geological State Park offers some of the most stunning natural beauty in Islamorada. There are five self-guided nature trails where you can read about the park and how it’s contributed to Florida’s history. 

Windley Key Fossil Reef Geological State Park

Make sure to stop into the visitor center before starting your tours to get brochures about the trails and gaze at the educational exhibits. Formed of Key Largo limestone and fossilized coral, the state park was once part of Florida’s east coast railroad.

Wear some sturdy shoes to walk along the eight-foot quarry walls and sections of the old coral. The exhibits at Windley Key will also teach you how the quarry machines work. You can even see and touch certain parts of the old pieces of the machinery.

Robbie’s Marina

If you’re an adrenaline junkie, stop by Robbie’s Marina. Located at Mile Marker 77 of the Overseas Highway, the marina offers an array of activities, including parasailing, shark fishing trips, and a chance to feed huge tarpons. For locals and tourists alike, Robbie’s Marina is one of the top places to go in Islamorada.

Robbie's Marina

If some members of your party don’t love watersports, Robbie’s Marina has plenty of relaxing activities, too. Sign up for a sunset cruise, boat charters, eco-tours, or just spend a few hours leisurely kayaking around the marina.

After a full day on the water, head to Hungry Tarpon Restaurant or the Thirsty Tarpon Bar

Long Key State Park

For an ultimate place to relax and experience the tranquility of the Keys, head to Long Key State Park. A short drive from Islamorada, the state park has plenty to do for the whole family. The two hiking trails are perfect for exploring the diverse plant and animal life of Florida. 

Long Key State Park

If you prefer to spend the day in the water, rent a kayak at the ranger station. Paddle through the canals in the mangroves or through the shallow waters for a clear view of Florida wildlife.

For even more adventure, camp along the shoreline or hike to one of Long Key State Park’s top camping spots.

Alligator Reef Lighthouse

Built in 1873, the Alligator Reef Lighthouse is just four nautical miles from the shores of Islamorada. Snorkeling and diving are the only activities available at the lighthouse. With your snorkeling gear, you can see over 500 species of marine life and a pirate hunter shipwreck underwater.

Alligator Reef Lighthouse

Before you explore, you can also listen to a short history of the lighthouse from a tour guide and learn more about what you’ll see underwater.

Alligator Reef Lighthouse is less than a 15-minute drive from Indian Key and the History of Diving Museum. You could easily visit all three top Islamorada attractions on the same day. 

Founders Park

Traveling with small children? Founders Park should be on your Islamorada bucket list. This 45-acre park is the main park on Islamorada, frequented by tourists and residents. The numerous walking and jogging trails at Founders Park are the perfect place to burn off those extra vacation calories.

Founders Park

The aquatic center has an outdoor Olympic size pool and an indoor swimming pool. Take the kids to the splash pad to cool off from the hot Florida sun. There are also several playgrounds to keep the tots entertained.

The shallow water beach at Founder Park has tiki huts, cooking grills, a pavilion, and large palm trees to string up a hammock.

Islamorada Beer Company

Islamorada is a dream come true for those who like to try local craft beers. The most popular hangout spot is the Islamorada Beer Company. Located a short drive from the beach, it’s the only combined brewery and distillery in the Florida Keys.

For those who aren’t huge beer lovers, Islamorada Brewery & Distillery also has cocktails and spirits crafted on-site. All the beers and spirits have an island vibe with flavors such as coconut and pineapple offered.

Get hungry while drinking? Spanky’s Kitchen is adjacent to the taproom and serves full meals and quick snacks.

Florida Keys Overseas Heritage Trail

Paralleling US Highway 1, The Florida Keys Overseas Heritage Trail is over 90 miles long. The paved roadway runs between Key Largo and Key West. Only available for use by pedestrians, it’s a safe place to hike, run, or cycle. You can also see 23 different Flagler Railroad Bridges, offering stunning views of nature and wildlife. 

Florida Keys Overseas Heritage Trail

If you plan to hop around the Florida Keys and the surrounding area, the Florida Keys Overseas Heritage Trail is perfect for getting from one point to the other quickly. The Everglades, Biscayne National Park, and Key Deer National Park are some of the main points of interest along and near the trail.

Florida Keys Brewing Company

Located in the Morada Way Arts and Cultural District, Florida Keys Brewing Company charms visitors with a beer garden that’s perfect for sitting and relaxing in the sunshine. The taproom offers options for pints, flights, or powder gills.

The beer garden at Florida Keys Brewing Co. is both pet- and kid-friendly. You can even start up a game of giant Jenga or cornhole. On the weekends, the garden also features live music from local bands.

The delicious beers at the craft brewery include year-round staples and seasonal releases. No matter what you order, every drop is brewed in the Florida Keys.

While all its beers are served on draft, the brewery also has options for takeaway in four-pack cans if you want to take some back to your hotel or down to the beach.

Library Beach Park

To get away from the crowds and have a quiet day alone or with family, head to the Library Beach Park. Located just off the Overseas Highway, the park is small and doesn’t usually get overpopulated, even in the busy tourist months. Let the kids get some energy out on the playground or have a picnic under the covered pavilion.

There’s a small public beach at Library Beach Park, but it’s not great for lounging or taking a walk. The mangroves are stunning to look at though. The small swimming hole is a great spot for cooling off or spending time with the kids.

Hurricane Monument

Many tourists to Islamorada miss out on The Hurricane Monument. Wedged between the Overseas Hwy and Old Hwy, the monument isn’t very big and doesn’t seem like much to look at at first glance. Built in 1937, the small memorial is carved out of local coral limestone.

Hurricane Monument

In September 1935, a deadly hurricane swept through the Florida Keys, mostly impacting Islamorada. The monument is dedicated to all the people of the island who lost their lives.

There isn’t much to do at the Hurricane Monument, but it’s an easy stop to learn about a small piece of Florida’s history and honor the lives lost.

Lignumvitae Key Botanical State Park

To get off the beaten track in the Keys, plan a trip to Lignumvitae Key Botanical State Park. The park gets its name from its virgin tropical forest, covered in over a thousand distinctive lignum vitae trees. Once blanketing the Upper Keys, these trees are prized for their dense wood and blue flowers said to have strong medicinal properties.

Accessible only by boat or kayak, the tour of Lignumvitae Key Botanical State Park centers around Matheson House. Built in 1919, the historic cottage now hosts a visitor center that contains exhibits detailing the island’s history.

Although ranger-led tours are currently suspended if you do get a chance to explore the hardwood hammock, be sure to wear full mosquito gear. Unlike most other parks in the Keys, this small slide of paradise is not sprayed for mosquitoes.


Ryan O'Rourke is a seasoned traveler and the founder & editor of Treksplorer, a fiercely independent guide to mid-range luxury travel for busy people. With over 20 years of extensive travel experience, Ryan has journeyed through over 50 countries, uncovering hidden gems and sharing firsthand, unsponsored insights on what to see & do and where to eat, drink & stay. Backed by his travel experience and in-depth research, Ryan’s travel advice and writing has been featured in publications like the Huffington Post and Matador Network. You can connect with Ryan on Twitter/X at @rtorourke.

DISCLAIMER: Treksplorer is a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for sites to earn advertising fees by advertising and linking to Amazon.com and its affiliated international sites.

DISCLAIMER: You'll notice that from time to time I link out to recommended hotels/tours/products/services. If you purchase anything through these links, I'll receive a commission. It won't cost you anything extra, but it will help keep me trekkin' on and delivering more free (and unsponsored!) travel information to you. Thanks :)