TOP 20 Things to Do In Islamorada, Florida

Islamorada, Florida might be one of the most popular towns in the Florida Keys (aside from Key West, of course!) Not surprisingly, there are tons of incredible things to do in Islamorada, which is why it’s my favorite choice when visiting the Florida Keys!

While other people might prefer Key Largo or Key West, Islamorada holds my heart because there is something for everyone! Oh, and I also got married here!

In this post, I’ll go over my top 20 things to do in Islamorada. From snorkeling to sports fishing, drinking local beer to fine dining, I promise you won’t be bored!

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All about Islamorada, Florida

Before we get into the list, here are some quick facts about Islamorada, with some helpful links to help plan your trip!

Islamorada is a major town/village in the Florida Keys, and it actually encompasses six different keys (Plantation Key, Windley Key, Upper Matecumbe Key, Lower Matecumbe Key and the offshore islands of Indian Key and Lignumvitae Key).

If you are driving from Miami, Islamorada is the second major village you will hit, right after Key Largo!

Islamorada is home to some incredible hotels, restaurants, and of course, activities!

A Detailed List of the Top 20 Things to Do in islamorada, Florida

1. Feed the Tarpon at Robbie’s

If you’ve heard of Islamorada, you’ve likely heard about Robbie’s! Robbie’s of Islamorada is most famous for its tarpon feeding activity, a must do when visiting the Keys!

You’ll get access to the dock for $2.50 per person, and then each bucket of fish is $5.00! This is a fun activity for the whole family, but be careful! Tarpon do have teeth 🙂

In addition to the tarpon feeding, Robbie’s also has tons of other activities, like jet ski rentals, kayak tours, sunset cruises, and more! They also have a great restaurant on site with yummy Bloody Mary’s!

2. Relax at the Islamorada Sandbar

The Islamorada Sandbar is one of my favorite places in the world! Less than a mile offshore, this popular spot will be packed with boats on your average Saturday.

Unfortunately, this spot is only accessible by water, so you’ll have to rent a boat, kayak, jet ski, or paddle board to get here. Or, you can book a specific tour that takes you there!

Once you arrive, you’ll be greeted by shallow, warm, crystal clear water! This spot is perfect for all ages and one of the best ways to spend an afternoon in Islamorada.

3. Go Shopping at Rain Barrel Village

The Rain Barrel Village is a historic artsy oasis in Islamorada that should definitely be on your list of things to do in Islamorada!

Here, you’ll find an open air garden, art vendors, galleries, boutiques, and speciality shops. It’s a great place to shop for souvenirs in the Keys!

You’ll know you’ve arrived at Rain Barrel when you see the GIANT spiny lobster on the side of the road. Her name is Betsy, and she is the second most famous landmark in the entire Keys, right after the Southernmost Point sign in Key West!

4. Have a Drink at Islamorada Brewing & Distillery

Since opening their doors in 2014, Islamorada Brewing & Distillery (originally Islamorada Beer Company) is a special spot in the Keys for locals and tourist alike.

They started as a small, local brewery and have grown into Islamorada’s only distillery, with delicious cocktails, food trucks, and an outdoor beer garden. Kids are welcome too!

My personal favorite beer here is the Queen Conch, but I recommend getting a flight so you can try a few different options! This is a great place to spend afternoon after being on the boat all day.

5. Try a Rum Runner at the Tiki Bar

Did you know the renowned Rum Runner cocktail was invented in Islamorada?!! Yep, it’s true!

The Tiki Bar at Postcard Inn has been operating in Islamorada since 1969, and according to their website, it is the birthplace of the rum runner. If you’ve never had a rum runner, it’s a particularly strong cocktail made up of rum, rum, and more rum! Oh, and a little banana liqueur and grenadine too 😉

The Tiki Bar is definitely worth a stop during your time in Islamorada. Plus, they have incredible food!

6. Eat all the Key Lime Pie at Blond Giraffe

Just outside of Islamorada in the town of Tavernier, the Blond Giraffe Key Lime Pie Factory is one of the best places to get this iconic dessert in the Keys! They have whole key lime pies (of course), but they also have key lime cookies, key limeade, key lime meringues, and more!

Trust me when I say you CANNOT leave the Keys without trying Key Lime Pie!

7. Rent Jet Skis from Whale Harbor

If you’re an adventure lover like me, this one is for you! Renting jet skis is one of my favorite things to do in the Keys, and Islamorada is the perfect place for it!

We typically rent with A1A Watersports in Islamorada! They offer daily jet ski tours starting at $129 for one hour or $200 for two hours. They also have boat rentals here.

8. Visit the Spa at Cheeca Lodge

If you’re looking for a little rest and relaxation during your time in Islamorada, I highly recommend checking out the spa at Cheeca Lodge. One of the only spas in the upper Keys, Cheeca Lodge offers a variety of treatments, from massages to sugar scrubs to facials!

In my opinion, Cheeca Lodge is one of the best hotels in Islamorada, and their spa does not disappoint!

9. Snorkel at Alligator Reef Light House

I’ve traveled to a lot of places over the years, but Alligator Reef Light House will forever be one of my favorite places on this Earth. If you’re visiting the Florida Keys, you need to make a point to check this spot out!

5 nautical miles off of Islamorada, this light house sits in shallow, stunning turquoise blue water. There’s no shortage of tropical fish and wildlife here. I’ve seen dolphins, turtles, sharks, eels, and other creatures over the years here (just no alligators!)

Unfortunately you will need a boat to visit here, or you can book a snorkel tour like this one that will take you out to the reef!

You can read more about visiting this spot in my Islamorada Snorkeling Guide!

10. Go Sports Fishing

Did you know Islamorada is the sports fishing CAPITAL of the world?! Well, now you do!

If you’re interested, you can go on an off-shore fishing charter and potentially catch incredible game like marlin, sailfish, dolphin (mahi mahi), tuna, and wahoo! Unfortunately, some fish can only be caught during certain times of year, but you can pretty much catch dolphin year round!

Off-shore fishing not really your thing? There are plenty of other, more low-key fishing trips you can do, like in the backcountry or in shallow reefs. Check out the different options at Bud N Mary’s Marina for the best options in the Islamorada!

11. Look for Manatees in the Mangroves

One of my favorite parts about living in Florida is getting to see Florida manatees! Lucky enough, there are lots of manatees in the Keys, so your chances of seeing one are pretty good!

You can often find them in canals and around resort docks throughout the Keys. However, if you really want to see manatees, I highly recommend this eco kayaking tour through the Kayak Shack!

12. Have a Flight of Beer at Fl Keys Brewing Co.

Islamorada has not one but TWO local breweries, and I love them both equally! I’ve already mentioned Islamorada Brewing & Distillery, so let’s talk about Florida Keys Brewing Company.

FKBC is the upper Keys’ first microbrewery and definitely has more of a local vibe than Islamorada BC. They have an outdoor beer garden that’s open to all ages. Plus, they host local events like trivia, live music, and art festivals!

They have some delicious beers. So delicious in fact we used them for our wedding! How epic is this beer bus?! Make sure to check out FKBC while you’re visiting Islamorada!

13. Kayak to Indian Key

Indian Key is one of the smallest and most unique state parks in all of Florida! Only accessible by kayak, Indian Key gives you a taste of old Florida. It’s open every day from 8am until sundown. On the island, you’ll find the ruins of an old town that existed in the 1800s!

To get here, I recommend renting kayaks from the Kayak Shack at Robbie’s of Islamorada. From there, it’s a quick 20-minute kayak across the seagrass beds. Keep your eyes peeled in the water and you may see some stingrays or sharks on the way!

14. Look for Dolphins

Almost every time we visit the Keys, we spot dolphins at some point while on the boat! There are very common on the bayside in the warm shallow water, but you can also find them on the oceanside as well!

However, if you don’t have your own boat while in Islamorada, I recommend a dolphin watching tour like this one for your best chance of seeing these incredible mammals in the wild!

15. Enjoy a Luxury Meal at Chef Michael’s

There are tons of incredible seafood restaurants in Islamorada, but Chef Michael’s is probably the most upscale, fine dining establishment.

My favorite part about Chef Michael’s is how they serve the exotic (and invasive) Lionfish in an effort to help safe the reefs! If you’re looking for a fancier dinner in Islamorada, this is the spot.

16. Relax at Founders Park

There are not many true “beaches” in the Florida Keys, contrary to popular belief! Founders Park in Islamorada, however, does have one!

In addition to a beach and swimming area, Founders Park also has a playground, marina, baseball fields, a barbecue area, and more! It’s a popular place for locals and tourists alike and makes a great spot for some afternoon relaxation.

17. Watch the sunset at Lorelei’s

Lorelei’s Restaurant and Cabana Bar is one of the best restaurants in Islamorada, no doubt about it!

But what makes it even more special is that it sits on the bayside, which means this casual beach bar is one of the best spots in Islamorada to watch the sunset! I recommend coming here about an hour before sunset, grabbing a drink and some conch fritters, and enjoying nature’s show.

In addition, they also have live entertainment, including music, magicians, and more, depending on the night!

18. Go on a Sunset Cruise

Speaking of sunsets, besides watching them at Lorelei’s, my favorite way to see them are on the water. This tour from GetYourGuide is the perfect way to enjoy the Florida Keys lifestyle and watch an incredible sunset. Plus, beer and wine are included!

19. Feast at the Shrimp Shack

Islamorada is home to not one, but TWO, different restaurants that have been featured on Diners, Drive-Ins, and Dives. The Islamorada Shrimp Shack is one of those restaurants, and it does not disappoint.

The Shrimp Shack lives up to its name, with a menu that includes shrimp fritters, shrimp chowder, bacon wrapped shrimp, shrimp and grits, and more! Kinda sounds like Forrest Gump.. right?! Make sure to stop here for a lunch or dinner during your trip to Islamorada!

20. Get Scuba Certified

I may have saved the best for last, but getting scuba certified is one of the most epic things you can do in Islamorada, Florida! Or, if you are already certified, you HAVE to do at least one dive trip while you’re visiting.

The Florida Keys are home to 9 sunken shipwrecks (and many more artificial reefs). Known as the “Wreck Treck”, this official trail has dive spots from Key Largo to Key West, with the Eagle Wreck sitting in the waters off Islamorada.

There are tons of other dive spots to check out in Islamorada, like Hens and Chickens, Davis Reef, the Bluff and more! Scuba diving is my favorite thing to do in Islamorada, hands down!

Final Thoughts

That’s a wrap on my TOP 20 things to do in Islamorada, Florida! As you can see, this town in the Keys, which actually spans a few different keys, is one of the most enchanting places in Florida!

From snorkeling at Alligator Lighthouse to kayaking through the mangroves, most of the adventures in Islamorada revolve around the water, which is just how I like it!

If you’re planning a trip to the Florida Keys, don’t forget to check out my other posts about this slice of paradise!
Ultimate Florida Keys Travel Guide
Miami to Key Largo Mini Road Trip
25 Things to Do in Key West
Best Time to Visit the Florida Keys