Things to do in Islamorada – Best of the Florida Keys

It may not be as famous as Key West or Key Largo, but Islamorada in the Florida Keys is a must stop on any road trip. Located south of Key Largo, Islamorada is known as “The Town of Islands,” consisting of four islands stretching 18 miles along the Overseas Highway. Long known as the sportfishing capital of the world, there are many things to do in Islamorada besides fishing. With microbreweries, urban restaurants, water sports and yes, even Key Lime Pie, Islamorada is sure to have plenty of outdoor activities to please everyone.

Islamorada Florida Keys

Having transportation is a must for visiting the Florida Keys. If you’re not driving yourself, check prices at enonomy bookings rent a car for a real Florida Keys road trip from Miami along the Overseas Highway to Islamorada and Key West. Having a car offers plenty of freedom to get around Islamorada and explore all the hidden gems.

The Florida Keys measure everything by mile marker, so when you’re looking for the address or location of each attraction, just keep an eye on the mile marker sign. It’s easy to find out, so let’s get started!

1. Robbies Marina

robbies navy islamorada key

Robbies Marina was voted the number one place in all of the Florida Keys that everyone should visit, and we agree. There are local shops and markets, water sports, a bar and restaurant and a waterfront deck. We had a delicious breakfast here and it was the first time we tried Key Lime Pie in the Florida Keys – yummy! It feels like the old Keys where life was relaxed and simpler and there isn’t a care in the world. Everyone seems so relaxed and happy here.

2. Parasailing Robbies Marina

parasailling in florida keys

It was our first time parasailing and it’s awesome! I can’t believe we had never done it before our trip to Islamorada Kay. Parasailing with Sundance Watersports. The parasailing adventure was a fantastic tour where we got to see the coastline and explore the waters a bit before taking to the skies for amazing views of Islamorada Key, the highway bridges, Alligator Reef Light and Indian Key. It’s safe, fun and so easy that anyone can do it! The guides were safe, fun and entertaining and kept a good eye on us to make sure we stayed safe in the sky.

3. Feeding the tarpon at Robbies.

what to do on purple island feed the tarpon at robbies.
The Tarpin are waiting to be fed

While at Robbies you have to try your hand at feeding the tarpon hanging out on the dock. The story of how it all started is incredible. In 1976, an injured tarpon was floating in the waters. Upon inspecting him, Robbie noticed that his jaw was open. They nursed him back to health and named him Scarface and eventually returned him to the water. Scarface came back again and again, bringing his friends with him, and today schools of tarpon gather at the docks waiting to be fed. It’s a thrill, and no matter how prepared you think you’ll be, when that tarpon jumps out of the water and snatches a fish out of your hand, you can’t help but scream with surprise and delight.

Tip: keep an eye out for pelicans on the dock, they’ll snatch the fish out of your hand when you’re not looking.

4. Water sports and activities

sup stand up paddleboarding at sunet in the florida keys

From Robbies Marina, you can book all the Florida Keys water sports you’ve ever dreamed of, from jet ski rentals, to stand up paddle boarding, sunset cruises or snorkeling, they have it all. Why not rent a kayak to explore the area? It’s 20 minutes to India Cay State Park or, if you don’t want to go too far, you can paddle around the corner to the mangrove system and look for manatees. If you like fishing, Islamorada Key is known as the sport fishing capital of the world.

Robbies is located at milepost 77.5.

5. Florida Keys Brewing Co.

florida keys brewing beer flight


Beer flight at Florida Keys Brewing Company.

The Florida Keys Brewing Company is one of the best places on the island for live music, a relaxed atmosphere and delicious microbrews. We took a tour of the brewery to learn about the fermentation and bottling process at this colorful and quirky business before heading to their beer garden and tasting room where we enjoyed a flight of 10 different beers. I can honestly say I enjoyed all of them. (Yes, I tried them all).

Located in the Morada Way Arts and Cultural District, this is a very cool place to hang out. You can book a room for the night right on their property at FlaKeys Vacation Rental. There’s only one unit, so something tells me it fills up fast.

6. Chef Michaels

dine at chef michaels purple isle.

Chef Michals is also located in the trendy Morada Way arts and cultural district, just down the street from the Florida Keys Brewing Co. is a great place to dine. This upscale seafood restaurant that was one of our favorite meals in the entire Florida Keys. Help save the reefs by ordering the lionfish (an invasive species that is threatening the Keys reef system. They offer vegetarian options and we have to say the Mahi Mahi and scallops were to die for.

7. Morada Way Arts and Cultural District

Speaking of the Morada Way Arts and Cultural District, be sure to spend a little time exploring it. It has become a mecca for artists who have set up shop among the restaurants and bars of this “Downtown Mainstreet” in the heart of the Florida Keys. Keep an eye out for the 1935 Hurricane Monument, known as the Hurricane Monument, which pays tribute to those who lost their lives. It’s a stark reminder of how powerful Mother Nature can be here. A famous place to stay here is the Green Turtle Inn, which has been a landmark since 1947. Even if you don’t stay there, go for a bite to eat.

8. Islamorada Beaches

purple island beach chair

The Florida Keys are for fun in the sun and Islamorada Key also has some great beaches. With warm waters, hot days and plenty of sunshine in the Sunshine State, you have to hit the beach when spending time in Islamorada.

Beaches in Islamorada Annes Beach is the busiest beach in Islamorada. There is a boardwalk, restrooms and it is a popular spot for kiteboarding and windsurfing. This small beach is situated on the channel. It is a good place for paddleboardingHoliday Isle Beach – Located at the Postcard Inn and Beach Resort, this is Islamorada’s nicest beach that is close to bars and amenities. You don’t have to be sitting at the resort to use the beach. But you must go to the Tiki Bar to try their original cocktail The Rumrunner, invented in 1950 by rum runners passing through the Keys.

9. Holiday Isle Resort – Raw Bar and Tiki Bar

famous tiki bar at holiday isle

Speaking of the famous Tiki Bar, the Postcard Inn Beach Resort really does have a spectacular setting on Islamorada. Even if you’re not staying at the resort, be sure to dine at the Raw Bar, the setting is beautiful overlooking the water and feeling the warm evening breeze. This is a great place to enjoy a cocktail and a slice of Key Lime Pie.

10. Florida Keys History and Discovery Center

If it’s a rainy afternoon or you just want to learn a little more about the fascinating history of the Florida Keys, be sure to visit the Florida Keys History and Discovery Center. This 7,500-square-foot waterfront museum houses exhibits about the indigenous peoples of the Florida Keys and the era of pirates and Spanish fleets, as well as the creation of the incredible Overseas Highway. The museum is open Wednesday through Sunday, 10 a.m. to 5 p.m.

11. Florida State Parks

purple isle offshore islands

Windley Key Fossil Reef State Park

Take a self-guided walking tour on nature trails made up of exposed fossilized coral reefs. Windley Key Reef Geological Reef State Park has five trails where you can explore nature and really know what you’re seeing with guidance provided by park rangers.

Indian Key Historical State Park

As mentioned above, rent a kayak from Robbies Marina and head to Indian Key State Park or join a hike. You can head out to see the remains of an ancient castaway colony, snorkel in the clear waters, or explore the trails surrounding this island state park.

Lignumviatae Key Botanical State Park

Another interesting stop in the Florida Keys is Lignumviatae Key Botanical State Park. It is home to the Lignum vitae tree (the wood of life) and is the best place in North America to see the densest tree in the world. The island is teeming with rare plants, birds and insects. If you can charter a boat, head out to explore from Robbies Marina.

Things to keep in mind when visiting some attractions.

Florida Aquarium

signal on purple island florida keys

We have mixed feelings about the Florida Keys Aquarium. We don’t usually go to aquariums or zoos because we don’t like to see animals in captivity. But we know that aquariums play an important role in conservation and awareness. They are a great way to introduce people to marine life and teach them to respect the oceans and species like sharks. But swimming with stingrays or having tourists pet and feed sharks is not (in our opinion) a good way to do that.

I love that they rescue and rehabilitate their marine life, but they should focus more on giving them sanctuary and letting humans see them from afar instead of forcing the animals to interact with people every day. We noticed that the staff and our guide seemed to love the marine life and seemed to believe in what they were doing, but I don’t think the sharks should be interacting with humans every day. The 20,000 gallon tank looks huge on paper, but inside, the sharks swim in circles.

Theater of the Sea

pelican on purple island

And speaking of which, please reconsider swimming with the dolphins at Theater of the Sea. Theater of the Sea is one of Islamorada Key’s main attractions and has been around since 1946 and has a beautiful setting where marine life could thrive in captivity. Although it is said that many of its species are rescued and can’t return to their natural habitat, that doesn’t mean they have to put on shows and swim with humans. They could turn it into a beautiful sanctuary and I hope they make the transition in the future. They have a sea lion program where they are trained to jump through hoops. I haven’t seen any of this since the 80’s and still won’t.

Most travel companies have moved away from excursions like swimming with dolphins in captivity. TripAdvisor stopped selling tickets for dolphin shows and swimming with dolphins in captivity (although they still allow reviews) and Intrepid Travel, among other travel companies, stopped all excursions that involved swimming with dolphins. Read Why you should never swim with dolphins on your vacation.

Diving and snorkeling

If you feel like interacting with sea turtles, dolphins and other marine animals, consider an introduction to scuba diving or even a discovery dive. Snorkeling is an amazing way to have an encounter. And if you have kids, hop on a glass-bottom boat.

Where to stay in Islamorada

dock at hadley house purple island

Postcard Inn at Holiday Isle – This is the most popular place to stay in Islamorada offering cottages and rooms overlooking the Marina and Atlantic Ocean. There are water sports on site and you can book scuba diving in the Florida Keys from here. If you don’t fancy snorkeling or scuba diving, glass bottom boat tours are also available.

Hadley House Resort – We stayed at the Holiday House Resort, a boutique resort with cottages. I recommend staying in the building that faces the water. The cottages are set back from the water and the hotel building seemed much better. The $25 resort fee covers the use of paddle boards and kayaks. There is parking and a pool.

And these are the best things to do in Islamorada Key. It’s much more relaxed than Key West and is a great place to spend a few days enjoying the sun.


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