While not as commonly known as Key West or Key Largo, Islamorada is a must-stop destination on any Florida Keys road trip. Nestled south of Key Largo, this charming area is celebrated as “The Village of Islands,” comprising four islands stretching 18 miles along the Overseas Highway.

Renowned as the sport fishing capital of the world, Islamorada offers a wealth of activities beyond fishing, including microbrews, urban dining, water sports, and delectable Key Lime Pie. It’s a perfect location for outdoor enthusiasts seeking diverse experiences.

Things to Do in Islamorada, Florida Keys

Having a vehicle is essential for exploring the Florida Keys. For those not driving, consider checking RentalCars.com for rental prices, allowing for an enjoyable Florida Keys road adventure from Miami down to Islamorada and Key West. With a car, you’ll gain the flexibility to navigate around Islamorada and uncover its hidden treasures.

Note: The Florida Keys are designated by mile markers, simplifying the location process for attractions. Just keep an eye out for the helpful mile marker signs. Let’s dive into the myriad of activities available!

1. Robbie’s Marina

Robbie’s Marina is consistently hailed as the top destination in the Florida Keys that visitors shouldn’t miss, and it’s easy to see why! The marina features local shops, markets, water sports, a restaurant, and a waterfront deck. Here, we enjoyed a delightful breakfast, marking our first taste of authentic Key Lime Pie in the Keys. Delicious!

The atmosphere feels reminiscent of old-time Keys, where life is laid-back, and worries are few. Everyone here exudes a relaxed and jovial spirit.

Blonde Giraffe Key Lime Pie Factory

If you’re a fan of Key Lime Pie, make sure to visit the Blonde Giraffe Key Lime Pie factory. For a tasty treat on the go, try their signature Key Lime dipped in chocolate on a stick! Don’t miss the Serenity Garden located in the back courtyard. Address: 92220 Overseas Hwy, Tavernier, FL 33070, United States.

2. Parasailing Robbie’s Marina

It was our inaugural experience with parasailing, and it was absolutely breathtaking! We can’t believe we hadn’t done it before our trip to Islamorada. Our parasailing adventure with Sundance Watersports was fantastic, granting us stunning aerial views of Islamorada, the iconic Highway bridges, Alligator Reef Light, and Indian Key.

The experience is safe, enjoyable, and surprisingly easy, making it accessible to everyone! The guides were professional, entertaining, and attentive, ensuring our safety at all times.

3. Feed the Tarpon at Robbie’s

While at Robbie’s, take a moment to feed the tarpon that gather around the dock. The history behind this feeding tradition is fascinating. In 1976, an injured tarpon was found in distress. Robbie noticed its torn jaw and nursed it back to health, eventually releasing it back into the water. Named Scarface, this resilient fish returned repeatedly, bringing its friends along, resulting in schools of tarpon eagerly awaiting their meals at the docks.

It’s truly thrilling! Be prepared for a delightful surprise when a tarpon leaps from the water to snag a fish from your hand.

• Hot Tip: Watch for the pelicans on the dock—they’re known to snatch fish right from your hand when you least expect it!
• Address: 77522 Overseas Hwy, Islamorada, FL 33036, United States

4. Water Sports and Activities

At Robbie’s Marina, you can indulge in all your Florida Keys water sports desires: from jet ski rentals to stand-up paddleboarding, sunset cruises, and snorkeling—there’s something for everyone! Consider renting a kayak to explore the local waterways.

Paddle for about 20 minutes to Indian Key State Park, or simply meander around the mangrove system in search of manatees. For fishing enthusiasts, Islamorada is renowned as the sport fishing capital of the world.

• Robbie’s is located at Mile Marker 77.5

5. Florida Keys Brewing Co.

The Florida Keys Brewing Company stands out as one of the premier spots on the island to experience live music and sample delicious microbrews. We took a brewery tour to learn about the fermentation and bottling processes at this vibrant establishment before heading to their beer garden and tasting room, where we enjoyed a flight of ten different beers. Each one was delightful!

Located in the Morada Way Arts and Cultural District, this brewery is a fantastic place to relax. For an overnight experience, consider booking a stay at FlaKeys Vacation Rental; however, availability is limited.

• Address: 81611 Old Hwy, Islamorada, FL 33036, United States

6. Chef Michaels

Situated in the trendy Morada Way Arts and Cultural District, just a short distance from the Florida Keys Brewing Co., Chef Michaels is the perfect dinner spot. This upscale seafood restaurant was a highlight of our Florida Keys culinary journey. By choosing the lionfish, an invasive species threatening the local reef system, you can contribute to reef preservation. Their vegetarian options are equally enticing, especially the Mahi Mahi and sea scallops.

Address: 81671 Overseas Hwy, Islamorada, FL 33036, United States

7. Morada Way Arts and Cultural District

While in the Morada Way Arts and Cultural District, take some time to explore. This burgeoning hub for artists is nestled among various restaurants and bars along “Downtown Mainstreet” in the heart of the Florida Keys.

Be sure to look out for the 1935 Hurricane Memorial, known as the Hurricane Monument, which pays tribute to those whose lives were lost during that disaster. It’s a poignant reminder of nature’s formidable power. A notable establishment in the area is the Green Turtle Inn, a landmark since 1947; it’s worth stopping by for a meal, even if you’re not staying there.

8. Islamorada Beaches

The Florida Keys are synonymous with sun-soaked fun, and Islamorada offers some fantastic beaches. With its warm waters, sunny days, and vibrant atmosphere, a beach day is essential during your visit to Islamorada.

• Beaches on Islamorada
  • Annes Beach is popular, boasting a boardwalk and amenities, making it a favored spot for kiteboarding and windsurfing.
  • This little beach is situated near the channel, offering a great location for paddleboarding.
  • Holiday Isle Beach, located at the Postcard Inn and Beach Resort, is the region’s finest beach and close to various bars and conveniences. You don’t need to be a resort guest to enjoy the beach—but stop by the Tiki Bar to sample its signature cocktail, the Rumrunner, created by rumrunners in 1950.

9. Holiday Isle Resort – Raw Bar and Tiki Bar

The celebrated Tiki Bar at the Postcard Inn Beach Resort is a stunning venue in Islamorada. Even if you’re not a resort guest, it’s worth dining at the Raw Bar, which boasts breathtaking views and a delightful sea breeze. Indulge in a refreshing cocktail and a slice of delicious Key Lime Pie.

• Address: 84001 Overseas Hwy, Islamorada, FL 33036, United States

10. Florida Keys History and Discovery Center

If you encounter a rainy day or simply wish to delve deeper into the captivating history of the Florida Keys, the Florida Keys History and Discovery Center is a must-visit. This oceanfront museum spans 7,500 square feet and hosts exhibits that showcase the Indigenous Peoples of the Florida Keys, spanning from the days of pirates to the establishment of the iconic Overseas Highway. The museum is open Wednesdays through Sundays, from 10 a.m. to 5 p.m.

• Address: 82100 Overseas Hwy, Islamorada, FL 33036, United States

11. Florida State Parks

Many Florida State Parks are accessible from Islamorada, whether by boat or car. Here are a few notable ones worth exploring.

12. Windley Key Fossil Reef Geological State Park

This park offers a self-guided walking tour along nature trails featuring exposed fossilized coral reef. Windley Key Fossil Reef Geological State Park boasts five trails for visitors to explore at their own pace while utilizing a guidebook provided by park rangers.

The 8-foot-high quarry walls allow for cross-sectional views of the ancient coral reef, shedding light on this site’s crucial role in Florida’s 20th-century history, with displays highlighting the machinery used to construct the Overseas Railroad.

13. Indian Key Historic State Park

As previously mentioned, you can rent a kayak from Robbie’s Marina and head to Indian Key Historic State Park or join a guided tour. Discover remnants of an old wrecking colony, snorkel in the crystal-clear waters, or explore the walking trails of this scenic island state park.

14. Lignumvitae Key Botanical State Park

A unique stop in the Florida Keys is Lignumvitae Key Botanical State Park, home to the famous Lignum vitae tree (the wood of life). This site showcases North America’s densest tree species, along with an abundance of rare plants, birds, and insects. Renting a boat to explore the area from Robbie’s Marina is highly recommended.

15. Scuba Diving and Snorkeling

If you want to swim with sea turtles, dolphins, and diverse marine life, consider taking an introductory scuba diving course, or try snuba or a discovery dive. Snorkeling is another fantastic way to interact with the underwater world. Families can also enjoy a glass-bottom boat ride, ensuring an unforgettable experience.

16. History of Diving Museum

The Florida Keys play host to the largest coral reef in the United States, and diving has significantly contributed to its development and industry. For diving enthusiasts, the History of Diving Museum features artifacts, cherished antiques, and documents about diving history in the Florida Keys and across 30 countries. Come see vintage armored diving suits, helmets, and a diving bell. Address: 82990 Overseas Hwy, Islamorada, FL 33036, United States.

Things to Consider When Visiting Islamorada Attractions

Mixed feelings arise regarding the Florida Keys Aquarium. While we typically avoid aquariums and zoos due to concerns about wildlife captivity, there’s no denying that they play a critical role in conservation and increasing awareness. They effectively introduce marine life while promoting respect for ocean ecosystems. However, experiences like swimming with manta rays or allowing tourists to feed sharks do raise ethical concerns.

I appreciate their rescue and rehabilitation efforts but believe they should prioritize sanctuary principles, allowing humans to appreciate marine life from a respectful distance. During our visit, the staff and our guide clearly displayed their passion for marine life, yet we felt uneasy about the frequent human interaction with the animals.

A point of contention lies with one of Islamorada Key’s main attractions: the Theater of the Sea. Operating since 1946, it features a 17-acre environment where marine life can thrive, though it permits tourist interactions with dolphins and includes marine shows. I’m not supportive of watching animals perform tricks for entertainment under duress.

The trend in travel companies is shifting; many are moving away from attractions such as swimming with dolphins in captivity. TripAdvisor has ceased ticket sales for dolphin shows and captive swims (though reviews are still accepted), and Intrepid Travel has halted tours involving captive dolphin swims.

• Read Why You Should Never Swim with Dolphins on Vacation.
• Canada has enacted a law prohibiting the captivity of marine life such as dolphins, porpoises, and whales. Learn more here.

Where to Stay in Islamorada

Postcard Inn at Holiday Isle – This is a preferred lodging choice in Islamorada, offering cottages and rooms with Marina and Atlantic Ocean views. On-site water sports and scuba diving opportunities are available. For those not keen on snorkeling or scuba diving, glass-bottom boat tours are also offered.

Hadley House Resort – We personally enjoyed our stay at Hadley House Resort, a charming boutique resort with cottages. I recommend selecting a unit with a water view, as the cottages are farther from the sea. A $25 resort fee covers the use of stand-up paddleboards and kayaks, along with parking and pool access.

These are the top experiences to discover on Islamorada Key, which offers a more relaxed vibe compared to Key West, making it an ideal getaway for a few days. Plus, with the abundance of fantastic water activities, you’ll find the perfect opportunities to tick off your beach bucket list while basking in the sun.