22 Fun Things to do in Islamorada, Florida Keys Enclave

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If you’re looking for fun in the Florida Keys, you’re going to love Islamorada Florida. There are so many things to do in Islamorada! This small town in the Upper Keys may not be featured in a Beach Boys song like Key Largo, nor as famous as perennially popular Key West, but there is so much to offer here.

I’ve been visiting the Florida Keys for years, and when I first visited Islamorada, I was most excited to see the sights from the Netflix series Bloodline (which I still highly recommend if you haven’t seen it yet). Much of the series takes place at a hotel called “Rayburn House,” which is shot at Moorings Village in Islamorada!

Located in the Upper Keys, Islamorada is often called the Village of Islands and is made up of six small islands.

Throughout the Florida Keys, there are ample opportunities for snorkeling, scuba diving, boating, and fishing — and Islamorada has all of these in spades. Fishing is especially popular, and Islamorada is often called the sportfishing capital of the world. But that’s not all — I also really enjoy Islamorada’s arts scene and craft brewing and distilling scene.

If you’re looking to travel up and down the Florida Keys from a central location, Islamorada is a pretty good base, just 20 minutes from Key Largo and an hour and 45 minutes from Key West.

Come to Islamorada for fresh seafood and brightly colored sunsets, craft beer and unforgettable souvenirs. This is one of the gems of the Florida Keys!

This post was published in January 2024 and was co-written by Adventurous Kate and Susan Stephens.

People crouched on a dock, feeding small fish to the giant tarpon fish in the water!
Robbie’s Marina is an absolute-must when driving through the Keys!

The Best Things to do in Islamorada

Feed the Tarpon at Robbie’s

Far and away, the most unique thing to do in Islamorada (and my personal favorite thing to do in Islamorada!) is feed the tarpon at Robbie’s of Islamorada. This is an absolute must in the Florida Keys. You buy a bucket of small fish, lean over the edge of the dock, and hand-feed them to the giant tarpon below!

This is thrilling and hilarious — especially if you have a slight fear of fish and larger fear of birds, like I do. (Why birds? Pelicans hang out along the edge, hoping to grab some of the tiny fish. Keep a decent distance from them them; they can bite.)

Get lots of photos and videos of you feeding the tarpon — this is a very Instagrammable activity.

After you get done feeding the fish, you can also kayak or paddleboard from Robbie’s or check out their restaurant, The Hungry Tarpon, to try some local seafood dishes. Their Trailer Trash Bloody Mary is legendary, featuring bacon, shrimp, a meat straw, pickled vegetables, and olives stuffed with blue cheese, pickles and pimentos.

If you eat outside, don’t miss popping your head inside to see the interior, covered with dollar bills! Feel free to tape a spare dollar of your own.

A colorful glass-blown fish in an art gallery.
Stop in the galleries of Islamorada for art like this.

Explore the Morada Way Arts District

Right in the heart of Islamorada is the Morada Way Arts & Cultural District, filled with several galleries, shops, and studios featuring treasures made by local artists. If you’re looking for a souvenir from your time in Islamorada, this is where I recommend you look.

The Morada Way Art Walk takes place on the third Thursday of every month, when parts of the streets are shut down from 6:00 to 9:00 PM, and the local stores stay open till late. The streets turn into a festival, with live music, food and drink, lots of artists showcasing their wares.

This artsy event is an absolute must if you time your trip to Islamorada right! It’s one of the best ways to meet some locals.

A woman biking on a cement road over the ocean.
Woman biking the Keys Overseas Heritage Trail, via Michael Rosebrock on Shutterstock.

Bike or Hike the Keys Overseas Heritage Trail

With 90 miles of trails Key Largo to Key West, this scenic corridor threads together numerous historical landmarks, ecological hotspots, and panoramic views of the Everglades and the Atlantic Ocean. Some people even bike the train the full length of the Keys!

The trail will take you alongside mangrove swamps and coral reefs, with some historic sites sprinkled in. Keep in mind that some parts are nice and quiet, while some parts are right up next to the highway. And no matter what you plan to do on the trail, it’s a good idea to pack plenty of water and sunscreen with you. Some sandwiches for a picnic would be fun, too!

If you’d like to explore by bike in Islamorada, you can rent bikes from Backcountry Cowboy, or electric bikes from Keys Ebikes. (As much as I love ebikes for getting up hills, you won’t be going up many hills in the Florida Keys!)

Access to the Florida Keys Overseas Heritage Trail is free of charge.

A round wooden sampler platter topped with several small glasses of beer.
Sampling them all at Florida Keys Brewing Co!

Try Local Craft Beer

I love dropping by local breweries on my travels, and Islamorada is home to some of the best in the Florida Keys. And the staff are amazing — because people who quit their conventional jobs to make beer for a living always have stories to tell!

First up is Florida Keys Brewing Company, Islamorada’s first microbrewery. Nestled in the heart of the Morada Way Arts & Cultural District, the family-owned establishment is renowned for its innovative brews. The tasting room is open daily, and their colorful beer garden is a fun place to relax and enjoy some board games along with your brews.

Not far off, Islamorada Beer Company offers more tasty craft brews. Their claim to fame is “Sandbar Sunday,” which encapsulates the sun-soaked lifestyle of the Keys. Try their citrusy Islamorada Ale or the hoppy Floriday for a perfect Keys beverage.

Not a beer person? There’s a wine spot, too! Islamorada Wine Co. is a wine bar featuring a wide array of boutique wines, and their tasting room offers a cozy atmosphere where you can sip and learn about their wine varieties. They’ve got a nice selection of charcuterie and other dishes to pair with their wines.

A diver examining a giant shipwreck in Florida.
The Eagle shipwreck in Islamorada Florida, via Shutterstock.

Visit the History of Diving Museum

Delve deep into the ocean’s secrets at the History of Diving Museum. As you can guess from the name, the museum showcases the history of diving around the globe, with artifacts and exhibits like the diving helmets used by early explorers to example of underwater habitats.

If you’re looking for things to do in Islamorada on a rainy day, this is a good choice!

Admission to the museum is $15 for adults, $13 for seniors, and $12 for veterans. Students with ID pay $11 and children 6-11 are just $7. Kids 5 and under receive free admission.

A stone memorial in Islamorada Florida remembering hurricane victims in 1935.
A memorial to victims of the 1935 hurricane, via Joni Hannebutt on Shutterstock.

Visit the Florida Keys History and Discovery Center

Here’s a great spot to immerse yourself in the rich history and culture of the Florida Keys. The Discovery Center offers a plethora of exhibits showcasing the region’s maritime heritage, natural environment, and Indigenous peoples.

Here, visitors can explore the storied past of the Florida Keys from a new perspective. You can delve into the tales of famous pirates, learn about Indigenous peoples and their customs, and marvel at the diverse marine life that inhabits the surrounding waters. The museum also hosts a variety of temporary exhibits.

Admission is $15 for adults, $12.50 for seniors, $6 for students, and kids under the age of 6 can enjoy free entry. 

People sitting on a wooden dock in the Florida Keys, enjoying the view just before sunset.
Sunset-watching is the local sport in the Keys!

Catch the Sunset at Marker 88

One thing I love about the Florida Keys is that everyone seems to be in a great mood! And one place to enjoy the sunset amongst lots of happy Keys visitors is Marker 88, a restaurant located on Plantation Key in Islamorada.

Come here to enjoy a perfect pink and purple Islamorada sunset. They have a nice cocktail menu, including a “coffee margarita” if you want to be a bit adventurous! And the food is excellent, too, with lots of seafood dishes and a raw bar.

And of course, there’s always key lime pie for dessert.

A calm sandy beach with a small beach hut and lots of tall palm trees.
Cheek Lodge’s grounds are worth the spa entry alone! Via Shutterstock.

Enjoy a Spa Day at Cheeca Lodge

If you’re looking to pamper yourself on your trip to the Florida Keys, I recommend you check out the spa at Cheeca Lodge, one of the nicest hotels in town. It’s also a decent way to get back to feeling like yourself again if you had a late night the night before!

Services here include a variety of massages – from traditional Swedish and Jade Stone to unique offerings like Hot Lava Shell Massage, a treatment that uses polished tiger clam shells to invigorate the energy flow! Other body treatments include hydrating wraps, exfoliations, and facials. And they often incorporate local ingredients, like Florida Keys sea salt and coconut oil.

While I didn’t get to try any of the spa services at Cheeca Lodge, I did get to join a Zumba class here! Check their website for the latest offerings.

Dozens of small boats anchored off a sandbar in clear, bright green water.
There’s nothing like a sandbar party in the Florida Keys! Via Shutterstock.

Party in the Ocean

Islamorada is definitely a destination that can bring the party — but not in your typical beach bar fashion! In Islamorada, you don’t party at a bar on the beach, you party IN the ocean.

The Islamorada Sandbar is located a mile offshore, around Mile Marker 84. It’s exactly what it sounds like — a sandbar in the middle of the ocean — but the people of Islamorada have turned it into the biggest party on the water. Some days you’ll find hundreds of boats along the sandbar, with people bringing their lounge chairs, grills, and more to set up in the shallow water of the sandbar.

Note that you cannot walk to the sandbar — it’s accessible by water only, even at low tide. Many boats will take you here but it can also be reached by kayak and paddleboard.

Another option for partying in Islamorada is to charter a private tiki boat to cruise around and relax with a cooler of your favorite drinks. You’ll drop anchor at the sandbar where you can kick back with a cool drink on the custom surfboard bar or take a plunge into the water for a refreshing swim.

The boat comes with four tower speakers so you can jam to your favorite tunes. And keep your eyes peeled – you might spot wildlife like dolphins, seabirds, and fish. Prices begin at $500 for a group of up to six. Definitely worth the splurge if you have a group.

A man fishing off a boat, a strong fish caught by his pole. The fish is so strong it's bending the fishing pole.
There’s nothing like fishing in the Keys! Via Shutterstock.

Go fishing

As the sport fishing capital of the world, it’s probably no surprise that fishing is one of the top things to do in Islamorada. Whether you’re deep sea fishing for the first time or an expert angler, there’s a fishing charter for you.

This fishing excursion is led by local captain Dave and an enthusiastic team of skilled shipmates. Depending on the target species for the day, you could be sailing locally or heading offshore for 20 minutes to an hour.

The aim is to fill the boat with as many fish as allowed, weigh them, then head back to the dock. There, the crew fillets and ices your catch, packing them for you to enjoy later — and that’s as fresh as fish can get! Prices for this exclusive experience begin at $1,600 per group.

People relaxing in a speedboat during a purple sunset in the Florida Keys.
Catching a gorgeous sunset is one of the best things to do in Islamorada Florida!

Enjoy a Sunset Cruise

Getting on the water in Islamorada is a must, and a sunset cruise is one of my favorite things to do in the Keys. There are several different options, and I recommend you read the descriptions carefully — some are more tame, while some are all-out booze cruises.

On this private sunset cruise, you’ll cruise to the bay side of Islamorada and enjoy some local wildlife before the sun sets. You might even catch the legendary Green Flash as the sun dips below the water! On the trip back, prepare for music, disco lights, and a dance-off under the stars. Prices start at $350 per group of up to six people.

How about a lovely sunset boat ride from Islamorada to the bay side of the island? On this group trip, you’ll take in the natural beauty of the Florida Keys and enjoy some sneaky peaks at the posh homes that line the waterfront. Take in the sunset with a killer view from all angles. Prices start at $86 per person.

Another option? Step onto a spacious 49-passenger pontoon catamaran and cross over to the bay side, where the sun dips into the Gulf of Mexico, painting the sky with hues of gold. Grab a drink and listen to crew members’ stories about the Keys and local marine life. You might even spot a dolphin if you’re lucky! Prices start at $76 per person.

People looking down at the blue underwater scene through glass panels in a glass bottom boat in Florida.
You’ll love seeing sea creatures through a glass bottom boat! Via LukeandKarla.Travel on Shutterstock.

Go On a Glass Bottom Boat Tour

If you’ve never been on a glass bottom boat tour before, the Keys is a great place to try it. You’ll get a sneak peek of the underwater world while staying dry in the process!

On this 46-foot glass-bottom boat tour, there’s plenty of room to kick back, relax, and drink in the stunning views. The captain and crew aren’t just pros at sailing — they’re also natural-born storytellers and eager to share their knowledge with visitors.

Alternatively, how about a night tour by glass-bottom boat? The Transparensea is a 46-foot boat with plenty of room to witness the sea creatures of the night (from a safe, dry distance!). With this boat tour, you’ll get special access to stunning reefs like Cheeca Rocks, Alligator Reef, and Caloosa Rocks.

Four snorkelers in the neon teal water at Pennekamp State Park in Key Largo.
Snorkeling in the Florida Keys is a must.

Go Snorkeling

It wouldn’t be a Keys trip without a bit of snorkeling, yet another of the best things to do in Islamorada. You can do it right off the beach in many areas or join a guided tour like the ones below.

In this 4-hour snorkeling and sandbar experience from Islamorada, you’ll get plenty of time to explore beneath the surface, followed by some time relaxing on the Islamorada Sandbar. This trip comes with gear, paddle boards, and refreshments, all led by a charismatic guide.

Another option is this private ecotour, which takes you around the mangroves to some of the top snorkeling spots — but don’t be surprised if you spot some exotic birds or even a crocodile on the way there!

If you’re looking for a shorter experience, this 2-hour snorkeling adventure takes place in a protected area, where you’re likely to see quite a bit of marine life underwater. Keep your eyes peeled for dolphins!

A few trees growing out of the surf on the edge of a white sand beach in the Florida Keys.
Anne’s Beach is the perfect relaxation spot in Islamorada Florida.

Relax on Anne’s Beach

Anne’s Beach is located on the southern end of Lower Matecumbe Key in Islamorada. This beach, a short walk from the Overseas Highway, is a tranquil spot in the Upper Keys.

Fringed with mangroves and palm trees, the beach provides ample shade and picnic spots. A boardwalk winds its way through several different beaches, allowing you to find your way to the perfect spot.

Don’t forget your snorkel and mask — the coral just off shore is nice here. And you should know that this is a pet-friendly beach.

A boardwalk leading through the mangroves on a small island. A weathered wooden sign has directions to the town square and Northwest st.
A quiet spot at Indian Key State Park, via Shutterstock.

Explore the State Parks

Islamorada is home to three different state parks, each of them worth visiting, with something different to offer. The entrance fee to each of these state parks is $2.50.

Indian Key Historic State Park is an enchanting little island that boasts a big history. Once the county seat for Dade County, this park was home to people who salvaged goods from ships that wrecked along the reef. Today, visitors can explore the island’s historical ruins, meander along the nature trail, or enjoy a range of water activities. It is only accessible by boat or kayak.

Windley Key Fossil Reef Geological State Park is home to an ancient coral reef that has since turned into fossilized limestone, giving a unique glimpse into Florida’s geological past. The park also features five trails where visitors can learn more about the area’s natural and cultural history. The visitors’ center, with its exhibits of the park’s flora, fauna, and geological history, is well worth visiting.

Lignum Vitae Key Botanical State Park is a breathtaking pristine preserve that hosts a variety of plant and animal species. Named for the Lignum Vita tree, the park is located on a small island and is only accessible by boat. The main attraction here is the stone Matheson House, built in 1919 and a throwback to the pioneer days.

A slice of chocolate syrup-topped key lime pie in a plastic container.
Stop at the Blond Giraffe for some of the best key lime pie in Islamorada Florida.

Eat All the Pie at the Blond Giraffe Key Lime Pie Factory

I’ll admit it — whenever I’m in the Florida Keys, I’m eating key lime pie at least twice a day. And Islamorada has a great place to sample it — the Blond Giraffe Key Lime Pie Factory.

Here they have lots of kinds of key lime pie available, including pie with meringue, whipped cream, chocolate, naked pies, and even key lime on a stick. They have espresso-based coffee drinks, key limeade, and a really beautiful garden in the back that is the perfect place to kick back with a slice.

And here’s a tip — you can get a whole pie for the cost of around four slices. So get a whole pie! You’re on vacation! 

A wooden dock perched near lots of palm trees in Key Largo, Florida.
Key Largo is a gem of a getaway.

Take a Day Trip to Key Largo

Key Largo is the first place you pass through when driving over from the mainland, and it’s just a 20-minute drive from Islamorada, so I highly recommend spending a bit of time in this beautiful place.

Key Largo is home to John Pennekamp Coral Reef State Park, which offers some of the best snorkeling in the Florida Keys. One of the best ways to experience it is to join a snorkeling trip. The mangroves along Key Largo are incredibly beautiful.

There are also some quirky shops in Key Largo, like Keys’ Meads, which makes a variety of meads (honey-based liqueurs that have come back into fashion lately) infused with lots of fresh local ingredients.

There’s also a lot of good food in Key Largo. Both The Bayside Grille and Skippers Dockside have great seafood. But Key Largo is home to my favorite key lime pie in all of the Florida Keys: Mrs. Mac’s. I stop by whenever I’m passing through!

Bright blue clear water leading to the white sandy beach on Bahia Honda State Park.; the land looks like a jungle
Calusa Beach in Bahia Honda State Park, via Shutterstock

Take a Day Trip to Bahia Honda State Park

Bahia Honda State Park is about an hour’s drive from Islamorada and is home to some of the most famous beach shots of the Keys. The beaches here are absolutely gorgeous, with views of the Overseas Highway and historic bridges in the background, and definitely among the best beaches in the Florida Keys.

Like everywhere else in the Keys, it’s all about enjoying the nature and slowing down. But the beaches here are some of the best, especially Calusa Beach. The water here is so clear!

I’d recommend coming here early if possible, especially if it’s a weekend or holiday, because it can get so busy that they close it to additional visitors. Entry to the state park is $2.50 per person.

And if you have time, the Turtle Hospital in Marathon makes a nice stop on the way back, where you can visit the sea turtles being nursed back to health by a dedicated staff.

People gathering at outdoor booths for the sunset celebration on the edge of the water in Key West.
Key West’s Sunset Celebration is a party every night!

Take a Day Trip to Key West 

What can I say about Key West that hasn’t been said? It’s one of the most fun places on Earth!! Of course, Key West deserves as much time as you can give it — ideally, at least three days. But if you don’t have that much time, you can do it in a day trip from Islamorada (1 hour and 45 minutes of driving each way).

How do you spend a single day in Key West? The Ernest Hemingway Home and Museum is a really interesting place to visit, where you can enjoy the architecture, stories of Hemingway’s life, and see the many six-toed cats (descendants of Hemingway’s beloved pet) that populate the building.

I also really love the Little White House, which was President Harry Truman’s vacation home. I love the mid-century decor, and the guides have lots of great stories about Truman.

And Duval Street is a must, filled with tons of bars, restaurants, and shops. And the Southernmost Point has a bright red and yellow buoy marking the southernmost point in the continental US, only 90 miles from Cuba!

And if you have time, finish with the Sunset Celebration in Mallory Square, filled with street vendors, performers, musicians, and more. Don’t miss the Cat Man, who performs with his circus cats!

People sitting in chairs watching the sunset on the beach in Florida.
A few days is a good amount of time to see the best of Islamorada.

How Much Time to Spend in Islamorada, Florida

If you want to explore the top sights of Islamorada, you can accomplish that in about two days. But who comes to the Florida Keys to rush from sight to sight? It’s all about soaking it in!

For that reason, I think 3-5 days is a nice amount of time to visit Islamorada, which should give you enough time to do a few day trips to other Keys while you’re based there. (Though I always recommend adding on a few days in Key West.)

And if you’re coming for a relaxing beach vacation, as long as you can! A week or longer would be lovely here.

The overseas highway in the Florida Keys, on a bridge that crosses along the shallow turquoise water, connecting the islands.
The overseas highway goes right through Islamorada.

How to Get to Islamorada, Florida

The closest major airport to Islamorada is Miami International Airport. You’ll find plenty of domestic and international flights landing here. From here it’s about a 90-minute drive to Islamorada.

Alternatively, Key West’s airport is about an hour and 45 minutes from Islamorada, but there are fewer flights that arrive here.

I highly recommend renting a car in the Florida Keys. I recommend Discover Cars for finding good rental car rates.

Uber is available in Islamorada (which I urge you to use when you’ve had a few drinks), as well as taxi services, and there is limited public transportation by bus throughout the Florida Keys.

A peaceful swimming pool surrounded by palm trees and deck chairs.
The pool at Cheeca Lodge is a great place to stay in Islamorada! Via Shutterstock.

Where to Stay in Islamorada, Florida

There are a variety of places to stay in Islamorada, both right on the Overseas Highway and tucked away along the water in more isolated locations.

Here are the top-rated places to stay in Islamorada:

Top-Rated Luxury Hotel in Islamorada: Cheeca Lodge Spa. This tropical resort is a gorgeous getaway, tucked away near the water. Amenities include the best spa in the area, a private fishing pier, and a nine-hole golf course. Suites feature ocean views and modern decor.

Top Rated Mid-Range Hotel in Islamorada: Ragged Edge Resort & Marina. This waterfront resort has apartment-style accommodation, ideal for those who want to do a bit of self-catering during their trip. Decor is simple, and the waterfront location can’t be beat.

Budget Hotel in Islamorada: It’s hard to find low-budget accommodation in this part of the Keys, but The Breezy Palms Resort offers a lower-cost option for Islamorada with high value for money. This beachfront location features apartment-style accommodation with small rooms, but a lot of personality.

Find deals on places to stay in Islamorada here.

Several scruffy looking outdoor stands in front of palm trees in the Florida Keys. One sign reads "Half day fishing $45."
Spring is my favorite time to visit the Florida Keys!

Best Time to Visit Islamorada, Florida

I’m a big fan of visiting the Florida Keys during the spring months — March through May — for wonderful weather that is warm enough to swim in the ocean, sunbathe a bit, and escape chillier temperatures up north. I think this is the best time to visit the Keys.

Winter is also a wonderful time to visit Islamorada and the Keys, though know that you might not be getting the summertime temperatures you expect. It’s still wonderful for enjoying sunshine in the outdoors, though! Expect chilly nights and bring a lightweight jacket.

Summer is incredibly hot and humid in the Florida Keys, and I don’t recommend visiting during this time of year unless you’re the kind of person who thrives in heat and humidity. (That was me as a kid, teenager, and young adult — but I can’t handle the heat the way I used to!)

While I’m a big advocate of shoulder season to most destinations, I only recommend spring, not fall, as fall is in the heart of hurricane season (which peaks in September and October) and I strongly recommend avoiding the Keys during this time. If you visit and a major storm arrives, listen to the authorities and follow their instructions.

Read More: Best Time to Visit the Florida Keys

A pink Cadillac turned into a boat, sitting at a dock in the Florida Keys, palm trees in the background.

Is Islamorada Worth It?

I love Islamorada and think it’s an essential part of a trip to the Florida Keys — even if it’s only to visit Robbie’s! So many of my favorite Keys memories were made here.

Do you need to actually stay in Islamorada? You don’t have to. I think you can enjoy a lot of the amenities of Islamorada if you base somewhere else — perhaps Key Largo, just 20 minutes up the road.

More on the Florida Keys:

More on Florida:

Have you been to Islamorada? Any suggestions?

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