Islamorada is the perfect place to experience true paradise. Referred to as the Village of Islands, you are never far from the water.
Islamorada is a perfect vacation destination for nature lovers, adventure seekers, and those looking for relaxation. Whether you want to be busy and active or slow down and soak in island life, you’ll love it here.
To do everything on this list, you’ll need to come back multiple times. And that’s ok because chances are you, you’ll want to anyways. And after all, isn’t that why it’s called a bucket list? I have tried to include all. the. things!!
Here is your ultimate bucket list of things to do in Islamorada.
Start Your Day With Coffee
One of my favorite ways to start the day in Islamorada is with a cup of coffee. Two of my favorite places to grab coffee in Islamorada are Midway Cafe and Coffee Bar or Cafe Moka.
Go Fishing
Islamorada is referred to as the Sportfishing Capital of the World. So if you want to go on a fishing trip, there really isn’t a better place than Islamorada. The area is renowned for its excellent fishing opportunities, with a wide variety of fish species available in both the Atlantic Ocean and the Gulf of Mexico.
Local captains know the best fishing spots so you will have your best chance at catching fish. If you’re newer, they can help you learn the ropes as well.
Feed the Tarpon at Robbie’s Marina
Robbie’s has a little bit of everything. You’ll find a restaurant; a marina where you can rent a boat, take a boat charter, or rent kayaks; and some locally owned small shops. But the biggest draw to Robbie’s is feeding the tarpon.
To feed the tarpon, you’ll pay a $2.25 to enter then $4 for a bucket of fish. The bucket comes with 5-8 fish so it can be shared between a few people. If you have never seen a tarpon before, it can be a little surprising because they are huge!
You’ll basically dangle a fish and they’ll leap out of the water to eat it out of your hand!
Paddleboarding and Kayaking
Explore the serene waters of Islamorada by paddleboard or kayak. The shallow, crystal-clear waters make it easy to spot marine life such as rays, dolphins, sea turtles, manatees, and a variety of fish.
Most resorts in Islamorada have paddle boards and/or kayaks included with the resort fee. If this is important to you, I do recommend calling to check ahead of time because some resorts charge an extra fee.
You can absolutely paddle right from your resort, but there are other areas of Islamorada that have more unique places to paddle. Indian Key Historic State Park and Lignumvitae Key Botanical State Park are perfect spots to paddle to then explore on foot.
Toilet Seat Cut
Toilet Seat Cut is probably the most unique thing to do in Islamorada. Basically, in the middle of the water is a long line of…. toilet seats!
Of course, there is a story behind all of these toilet seats lined up in the water. The area started as a man-made channel (it’s illegal to do this now). A homeowner wanted to get to his favorite restaurant faster so he created a channel to do it. Other boaters also used the channel so it grew through the years.
In 1960, Hurricane Donna flung debris throughout the island and into the water. Rumor is that a toilet seat was found hanging on one of the posts marking the channel. In their good humor, locals brought their toilet seats to “decorate” the other channel markers.
Visit the Theater of the Sea
Theater of the Sea has been around since the 1940s! They have tons of animals to see – parrots, dolphins, sea lions, nurse sharks, stingrays, and more. They have shows throughout the day and you can pay more for a more interactive experience.
There is a beach-type area where you can swim and they do a boat tour as well.
Relax at Anne’s Beach
Anne’s Beach is pretty secluded. I’d say a lot of people visit throughout the day but not many stay. There is a really nice boardwalk that takes you through the mangroves with gorgeous water views. The water is shallow, making it ideal for relaxing, especially if you have kids.
Take an Eco-Tour
An eco-tour will take you kayaking through some of unique Islamorada ecosystems. You’ll kayak through mangroves. Along the way, you never really know what you’ll see from interesting birds to different marine life. Eco tours are a great way to connect with nature and get away from it all.
Explore Windley Key Fossil Reef Geological State Park
Windley Key is a historic site due to its fossilized coral formations. The formations date back to some ancient coral reefs from 125,000 years ago. It used to be a quarry for the construction of Henry Flagler’s Overseas Railroad in the 1900s. Fun fact: you can still see remnants of one of the bridges from the railroad at Bahia Honda State Park.
There are also some trails you can take while you’re there.
Participate in Water Sports
If you want a bit of action, Islamorada has options for that, too. You can try jet skiing, parasailing, or kiteboarding. There are rental shops and guides throughout the island.
Shop or Eat at The Trading Post
The Trading Post is a cute little area that has a clothing boutique, a boho plant shop, a coffee shop, and a burrito restaurant. They all share the same space so you can easily visit all of them at once.
Bike or Walk the Keys Overseas Heritage Trail
There is a 106 mile bike trail that goes all the way from Key Largo to Key West. It isn’t completely finished and some of the sections of the trail involve being right next to the Overseas Highway on a narrow shoulder.
The trail is in tact in Islamorada, though. It’s not hard to find, just head towards US-1 (the Overseas Highway) and you’ll see a thin sidewalk along the road. This is a great spot to bike or walk.
Go to the Islamorada Sandbar
Spending the day at the sandbar is one of the most popular things to do in Islamorada. It’s actually so popular that the Islamorada Brewery made a beer called Sandbar Sunday.
The sandbar is around one mile offshore and you can easily see it from land. It’s actually pretty fun to watch all the boats come and go. A lot of people come to the sandbar to swim, wade, and lounge in the water. Some people go all out with grills and full-on bars.
Normally when places get crowded, I like to avoid them but at the sandbar, being busy is all part of the fun. Weekends and holidays are the busiest and at times it can get a bit rowdy but you can avoid that by just anchoring a little farther away from the busiest spots.
Get a Treatment from the Spa at Cheeca Lodge
For some true R&R, you can get a treatment from the Spa at Cheeca Lodge. Cheeca Lodge is one of my favorite places to stay in Islamorada, just the grounds of the resort are tranquil and relaxing without even stepping foot into the spa. It’s one of the best ways to relax!
You can book almost any kind of spa treatment you could want. They have facials, body treatments, massages, and more. There are 6 treatment rooms, a fitness center, an adults-only lap pool, poolside cabanas with butler service, and more.
See the Largest Lobster in the World & Go Shopping at the Rain Barrel
You can’t miss the Rain Barrel. It’s right on US-1, marked by the world’s largest lobster right out front. The lobster statue is 30 feet tall. But don’t stop there because you’ll want to explore the Rain Barrel, too.
The Rain Barrel Village is a collection of several locally owned, small shops located in one place. From the front, it doesn’t look like a large place but the back of it expands and it’s actually a pretty large area. It’s a fun spot for local art, clothing, jewelry, and other souvenirs.
Grab a Beer From the Florida Keys Brewing Co.
There are two breweries on the island, located within about a mile of one another and I recommend visiting both if you have time. Florida Keys Brewing Co is colorful with a huge outdoor beer garden.
They often have live music and I appreciate that they experiment with different beer. Every time we go, there is usually a new beer to try along with their classics. They do have flights available as well. If you’re hungry, there is a taco food truck on site and they are some of the best tacos I’ve ever had. Perhaps my favorite part about the brewery, though, is their cat who may or may not be there when you are.
Drink at Islamorada Brewing and Distillery
Islamorada Brewing is the other brewery in Islamorada. They also have a large outdoor area with live music. They also have a larger indoor area if you happen to be visiting when it’s really hot. My favorite beer is the No Wake Zone which is a coconut key lime ale – tastes like vacation! One thing I really like about this brewery is that they also serve homemade cocktails. I highly recommend the key lie colada, but you can even get a flight of their cocktails, which is really unique for a brewery. They also have a food truck that serves bar-type food.
Get a Cocktail at Crooked Palm Cabana
Crooked Palm Cabana was born from Islamorada Brewing and Distillery. They became so popular that they recently opened their own location separate from the brewery. I have been drinking their vodka sodas for quite a while and can see why they branched out. This location has a full menu as well as craft cocktails. The space is sophisticated yet laid back, so no matter what you will fit in.
Try Local Wine at Islamorada Wine Co
If you’re more of a wine enthusiast than a craft beer lover, check out the Islamorada Wine Co. It’s a casual and relaxed wine bar with charcuterie boards and small plates. If you are there on Sunday, they do serve a Sunday brunch.
Lignum Vitae Key Botanical State Park
Lignum Vitae Key Botanical Park is an island that’s only accessible by boat. The biggest attraction is the Matheson House, which was built in 1919 by William J. Matheson. He was a chemist who built the home as a vacation home for his family and friends. Today, the home serves as the island’s visitor’s center.
The island was named after the Lignum Vitae tree. It was once abundant but was over-harvested.
Try Something New at the Blond Giraffe
If there’s anything that come in key lime pie flavor, then the Blond Giraffe will have it. They have classic key lime pies, taffy, cookies, and so much more. My go-to is a chocolate covered key lime pie on a stick.
If you are there on a nice day, I highly recommend checking out their garden in the back. They have tons of plants and foliage out there and it’s a great spot to eat your dessert. You can also hang a love lock.
Visit a Restaurant That’s Been on TV
If a restaurant is good enough to be featured on TV, then chances are it’s pretty good. Here are some restaurants in Islamorada that have been featured on TV:
- Green Turtle Inn was featured on Diners, Drive Ins, and Dives for snapping turtle chowder
- MEAT Eatery and Tap Room was on Diners, Drive Ins, and Dives for amazing burgers. This is a little hole in the wall place with some of the best burgers I’ve ever had. They also have their own homemade condiments.
- Islamorada Shrimp Shack was on Diners, Drive Ins, and Dives for shrimp fritters. This is another hole in the wall with some of the best shrimp I’ve ever had.
Visit the History of Diving Museum
The History of Diving museum goes back 3,000 years to the history of diving. This is a great stop for anyone interested in diving. It is such a unique museum. It also has one of the world’s largest collections of diving memorabilia such as antique diving helmets, old deep-sea exploration equipment, suits, and much more. It is incredible how we got our start exploring the deep parts of the sea many years ago and gave me a much bigger appreciation for our ability to do things like scuba dive.
Snorkel at the Alligator Reef Lighthouse
If you have seen any pictures of Islamorada, then you’ve probably seen a picture of the Alligator Reef Lighthouse. It’s a popular spot for good reason. All around the lighthouse you’ll find crystal clear waters and over 500 species of marine life. This makes it a great place to snorkel or dive.
Learn about the 1935 Hurricane at the Hurricane Memorial
In 1935, a hurricane hit Islamorada with an estimated 18 foot storm surge. Known as the Labor Day hurricane, it took the lives of 485 people, many of them being World War I Veterans. The day of the storm, a train was sent to evacuate them but the storm’s high winds knocked the train off its tracks.
There is a memorial to those who lost their lives. The memorial stands 18 feet high for the 18 foot storm surge.
Learn About History at the Florida Keys History and Discovery Center
The Florida Keys History and Discovery Center is located just outside of the Islander Resort (a gorgeous resort in Islamorada that I highly recommend). It’s a small space filled withhistory. You’ll learn about shipwrecks, pirates, hurricanes, pineapple farming, and all of the other history that made the Florida Keys a place we love. There are artifacts, a movie theatre, traveling exhibits, and aquariums showcasing the coral reef ecosystem.
Kayak to Indian Key Historic State Park
The Indian Key Historic Park used to be a little town. It is now abandoned but you can still see some of the historic buildings. It’s a great place to hike, fish, snorkel, swim, and view wildlife. It’s 11 acres only accessible by boat or kayak.
Enjoy Fine Dining
Islamorada has some great fine dining options as well. Here are some favorites:
- Pierres for gourmet world cuisine with sunset views
- Chef Michael’s for upscale seafood & New American entrees
- SHIMA for sushi
- Ziggie and Mad Dog’s for a steakhouse in a bar-type setting
- Atlantic’s Edge (at Cheeca Lodge) for innovative seafood dishes located right on the water
Play Sports at Founders Park
Founders Park in Islamorada is a huge 45-acre park with outdoor activities for all ages. There is also a Visitor’s Center is also located right outside of the entrance of the park.
For an $8 admission fee, visitors can enjoy a wide range of amenities and recreational opportunities. There is a splash pad for the kids, a shallow water beach area, playgrounds, picnic areas, and walking trails. Plus, there are tons of sports activities including tennis courts, an outdoor fitness park, basketball court, soccer fields, volleyball courts, and pickleball courts. There is also a walking trail and an amphitheater. They also have a huge pool but there is an additional fee to enter the pool.
Enjoy a Waterfront Meal
When in the Florida Keys, you must eat at a waterfront restaurant at least once. There are plenty of waterfront restaurants in Islamorada.
Here are my favorites:
- Square Grouper
- Morada Bay Cafe
- Lazy Days
- Lorelei’s
- Hog Heaven
Go on a Sunset Cruise
Taking a sunset cruise in Islamorada can be a fun way to get on the water. Sunset cruises also tend to be a big cheaper than some of the other boat charters. Sunsets in the Florida Keys are breathtaking and seeing them from the water only makes them more special. If you’re lucky, you might even see a sea turtle or dolphins.
Morada Way Art Walk
If you happen to be in Islamorada on the third Thursday of the month, you can’t miss the monthly Art Walk. The walk is held by the Morada Way Arts and Cultural District (read more about them in the next section) and they have tons of vendors gather along their streets and buildings. This is right by the Florida Keys Brewery, so you can easily step in for a good craft beer, too. There is live music and the vendors are so friendly. It’s so much fun!
Wander the Morada Way Arts & Cultural District
The Morada Way Arts and Cultural District is a nonprofit that created a small but lively arts-based community in Islamorada. They take up around 6 blocks mostly on Morada Way in between the Green Turtle Inn and the Hurricane Monument.
They created a beautiful area where they want people to gather and enjoy galleries, restaurants, and studio spaces. It’s vibrant and lively but most of all, everyone is so welcoming and happy to share their spaces with you.
As strong members of the community, they also hold community events and festivals. One of the most popular is the Art Walk, which occurs the third Thursday of every month. The whole street opens up with vendors, local artists and retailers, food options, and live music. It’s a really fun experience.
Eat Key Lime Pie
When in the Florida Keys, you have to eat key lime pie! There are tons of places to grab a slice from, basically every restaurant will have slices of key lime pie. You can also grab a slice from the Blond Giraffe or The Trading Post which is a small 24 hour grocery store.
I hope this bucket list gave you some good ideas on things to do whether it’s your first time visiting or whether it’s one of your favorites. I know that there are plenty of things to do in Islamorada for you to have the absolute best time on your trip!
