Top 15 Activities in Islamorada, Florida

Situated approximately midway between Miami and Key West, Islamorada is referred to as the Village of Islands. This area comprises five keys positioned along the Overseas Highway, making it a strategic location to pause en route to Key West.

However, to regard Islamorada merely as a stopover would be a significant oversight. There is an abundance of activities and sights to explore, both on the islands themselves and in the pristine, reef-filled waters offshore.

You can engage in snorkeling amidst vibrant marine ecosystems, paddle to a ghost town on an uninhabited island, traverse mangroves, discover fascinating fossils within a quarry, or arrange a charter in one of the premier sportfishing locales worldwide. 

Moreover, this is merely a glimpse of what awaits. You also have the option to unwind completely, drifting at a sandbar or relaxing on a beach beneath the shade of a palm tree.

1. History of Diving Museum

Source: The History of Diving Museum / Facebook

Established in 2005, the History of Diving Museum boasts a remarkable collection of artifacts pertaining to humanity’s exploration of the oceans.

The museum operates daily from 10 AM to 5 PM, with guided tours available for those seeking a deeper understanding of the exhibits they encounter.

The displays feature diving apparatus, photographs, and firsthand historical narratives regarding significant maritime events. 

What particularly fascinated me was the striking assortment of vintage diving helmets from over 20 different countries. Among these, an intact Iron Mike from 1930 stands out among the atmospheric diving suits.

Additionally, the museum offers interactive experiences to engage younger visitors, including an enjoyable scavenger hunt.

2. Keys History and Discovery Center

Source: Florida Keys History & Discovery Center / Facebook

For those visiting the Keys and Islamorada for the first time, the Keys History and Discovery Center serves as a valuable resource to gain insight into the area’s history, ecology, and culture.

Located at the Islander Resort, the center spans two floors with picturesque views of the water.

I was captivated by the displays detailing Flagler’s Overseas Railroad, the devastating 1935 Labor Day Hurricane, and a 16th-century anchor salvaged from a wreck on the reef. 

Another notable feature is the Coral Reef Exploration Exhibit, which includes three aquariums showcasing the diverse marine life found just offshore. This exhibit was developed in collaboration with the esteemed Mote Marine Laboratory.

3. Robbie’s of Islamorada

It is challenging to encapsulate everything offered at this establishment on Lower Matecumbe Key. Primarily, Robbie’s serves as a convenient hub for charters and watersport rentals. 

Situated within one of the world’s premier fishing hotspots, you can arrange fishing charters on the reefs or in the Everglades’ backcountry. Notably, split charters are available, allowing you to share the cost of a private charter with another group.

In addition to this, Robbie’s offers kayak and paddleboard rentals, jet ski tours, parasailing, snorkeling excursions, eco-cruises, and boat rentals, should you wish to explore independently.

However, Robbie’s may be most recognized for the large school of tarpon that congregates around the dock. With more than 100 of these fish present, you can purchase a bucket of baitfish to feed them. At times, one may leap from the water to grasp food from your hand.

4. Windley Key Fossil Reef Geological State Park

Source: Fredlyfish4 / shutterstock

At the beginning of the 20th century, workers quarrying limestone for Henry Flagler’s Overseas Railroad uncovered substantial fossil deposits.

The remains of diverse ancient coral species are exquisitely preserved within the quarry’s eight-foot walls, located in a lush hardwood hammock.

Windley Key provides a rare opportunity to observe such remarkable fossils in situ. Guided tours are available from December to April, though visitors may also explore at their own pace.

I thoroughly enjoyed walking the trails, where remnants of 120-year-old quarry machinery are present, alongside a rich variety of native plant and tree species in the hammock. I would recommend utilizing a guidebook for additional engaging information about the various trail highlights.

5. Alligator Reef Lighthouse

No matter how you reach this historic lighthouse, be it via charter, wave runner, or rental boat, it is an experience that should not be missed.

Located north of its namesake reef, Alligator Reef Lighthouse was constructed in 1873. Despite the name’s implication, there are no alligators in this saltwater environment; the name derives from the USS Alligator, a schooner lost on the reef in 1822.

The lighthouse, built with an iron skeleton frame, was decommissioned in 2015; however, efforts by a dedicated group have raised substantial funds to restore the site. At the time of writing, solar-powered lights had just been installed to illuminate the structure.

The true pleasure of visiting Alligator Reef Lighthouse lies in the clarity of the waters and the abundant marine life that can be found in the surrounding shallows. I can genuinely say I have never encountered such clear water and witnessed an impressive number of barracuda.

6. Founders Park

Adjacent to Rain Barrel Village, Founders Park is set on 40 scenic acres by the bay, serving as Islamorada’s community park. One of its standout features is a stunning sandy beach situated within a shallow cove, flanked by palms and mangroves.

The park is a favored destination for nearshore snorkeling, and during my brief visit, I spotted a nurse shark, rays, blue crabs, and a remarkable array of fish.

Furthermore, Founders Park boasts numerous amenities, including an Olympic-sized pool, a splash pad, a marina, a dog park, and various sports facilities such as baseball/softball, tennis, pickleball, soccer, and basketball.

7. Rain Barrel Village

An iconic figure along the Overseas Highway for approximately 40 years is Betsy, a giant fiberglass spiny lobster. This anatomically accurate sculpture measures 400 feet long and stands 30 feet high.

Betsy marks the entrance to Rain Barrel Village, a renowned complex of studios and galleries showcasing hundreds of local artists. In a rustic environment, shaded pathways navigate through vibrant gardens, leading to various studios.

I believe there is no better location to procure authentic souvenirs in the Keys. Offerings range from sculpture and glass work to beachwear, paintings, jewelry, home decor, and much more. Visitors can also enjoy refreshments at the Lobster Shack Cafe, which serves sandwiches, snacks, fresh juices, and excellent coffee.

8. Islamorada Brewery & Distillery

This establishment opened its doors in 2014, initially as a craft brewery, subsequently adding the first and only distillery in Islamorada in 2017. 

Conveniently located along the Overseas Highway in Upper Matecumbe Key, Islamorada Brewery & Distillery offers a variety of beers and spirits.

Among the beer selection are favorites such as Sandbar Sunday (American Wheat Ale), Channel Marker IPA, and Islamorada Ale, which carries a citrusy flavor. 

Additionally, with a 100-gallon still and oak barrels for aging, the distillery produces a notable selection of rums, gins, and vodka. A highlight is the Dark Barrel Aged Rum, and flightable cocktails are available for those indecisive about their choice.

I particularly enjoy the food truck on-site, which operates from Thursday to Monday, serving burgers, wraps, and small pub-style dishes with a Keys twist.

9. Islamorada Sandbar

Located about a mile offshore is one of Florida’s most celebrated sandbars. Accessible only by water, many options are available to you in Islamorada. 

You can paddleboard, kayak, use a wave runner, or partake in various private or semi-private excursions arranged by local operators such as Robbie’s and Key Largo Adventures. My experience at this idyllic spot included glistening shallow waters, ideal for swimming, snorkeling, or simply floating. 

During hot summer weekends, the sandbar transforms into a vibrant gathering place with over 300 boats anchored nearby. The atmosphere is lively and festive with music playing and boats providing food vendors.

10. Indian Key Historic State Park

Source: Phillip Sunkel IV / shutterstock

Another unique destination to explore by water from Islamorada is a ghost town located on a quaint island. Indian Key was historically the initial seat of Dade County, a community of ‘wreckers’ engaged in salvaging materials from shipwrecks along the reefs. 

Established in 1836 amidst the Second Seminole War, the island was later abandoned following a raid by Native Americans.

Site remnants remain, providing history enthusiasts with a fascinating glimpse into the past. I found that the most enjoyable way to explore Indian Key is by kayak. 

The paddle from locations like Robbie’s is straightforward, allowing ample time for snorkeling or exploring the historic ruins.

11. Anne’s Beach

Source: Steve Heap / shutterstock

The Overseas Highway runs directly next to this beach at the southwestern tip of Lower Matecumbe Key. Named in honor of environmentalist Anne Eaton, Anne’s Beach features a small yet inviting stretch of sand along calm waters.

For me, it serves not as a place to spend an entire day but rather as a delightful spot for a walk or a picnic. A boardwalk winds through the mangroves parallel to the highway for about a quarter-mile. 

This location is excellent for wildlife observation, with fish visible in the clear waters and a variety of crabs and wading birds, such as ibises. The prevailing breezes and expansive shallow waters also make this a prime spot for kiteboarding.

12. Florida Keys Brewing Company

Established in 2012, the Florida Keys Brewing Company is notable for being the first production brewery in the Florida Keys. 

Even today, amidst a proliferation of craft breweries, it stands out as the sole brewery to produce and package its beer locally within Islamorada. If you frequent bars or restaurants throughout the Keys, the name FKBC may be familiar to you. 

During my visit to the tasting room, I encountered 20 beers on tap, featuring a variety of refreshing IPAs and lagers, perfectly suited for the tropical climate. The beer garden is particularly charming, adorned with beautiful foliage, yard games, and a stage for live performances. 

The permanent food truck here serves excellent tacos and burritos, where orders can be placed at the window, and food is brought to your table.

13. Library Beach Park

The name of this beach is significant, as it is situated directly behind the Monroe County Public Library. This tranquil location features a slim stretch of sandy shoreline along a mangrove channel. 

Though it may not appear impressive at first, I found Library Beach Park to be quite delightful. The waters are remarkably clear, providing a pool-like environment that is ideal for families with young children. However, it is important to note that a current runs through the channel, which should be considered.

In addition, there is a basic yet pleasant park area featuring grassy spaces, playground equipment, and a chickee hut equipped with two picnic tables.

14. The Florida Keys Overseas Heritage Trail

Source: Michael Rosebrock / shutterstock

For those inclined to pedal, it is possible to ride a bicycle from Lower Matecumbe Key to Key Largo. 

The Village of Islands boasts the longest completed segment of the Florida Keys Overseas Heritage Trail. 

Utilizing existing paved paths and sidewalks, along with segments along the railbed of the Overseas Railroad, this state trail is slated to connect Key Largo to Key West, spanning 106 miles. In Islamorada, this means one can leave the vehicle behind and navigate most locations by bicycle.

Among the points not included in this list is The Florida Keys Memorial. Crafted from coral limestone extracted at Windley Key, this memorial commemorates over 400 individuals who perished in the 1935 Labor Day Hurricane.

15. Whale Harbor Restaurant and Seafood Buffet

Source: Whale Harbor Seafood Buffet / Facebook

I readily acknowledge that visiting the Florida Keys entails enjoying an abundance of seafood. The Whale Harbor Restaurant and Seafood Buffet stands as an ideal venue for such indulgence.

This local establishment has been a longstanding icon for over a century and is highly regarded for its exquisite Seafood Feast Buffet.

The price during my visit was $39.95, and an impressive array of seafood was presented, including grilled mahi-mahi, freshly shucked oysters, ceviche, crab cakes, crab legs, grilled salmon, shrimp, and an abundance of other options, all prepared by a dedicated culinary team.

Make sure to save room for the dessert aisle, featuring delectable tres leches cake and traditional Cuban flan.