Top 7 Best Bars in Islamorada

A trip to a tropical paradise isn’t complete without a cocktail in hand overlooking the clear blue waters. And on this, the best bars in Islamorada do not disappoint.

Islamorada is our favorite stop when traveling from Miami to Key West. We typically spend two to three nights in Islamorada on every Florida Keys road trip.

This stretch of the Florida Keys has everything from tiki bars where you can expect a little umbrella in your drink to a sports bar where you can cheer for your favorite team. There’s even a brewery with a tasting room and the best beer garden around.

No matter where you end up, the best bars in Islamorada totally have the island vibe down. Each one has a relaxed feel, live music, and drinks those delicious tropical flavors. Yum!

Here are the top 7 best bras in Islamorada where we head for a drink or two!

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1. Lorelei Cabana Bar

When it comes to the best place to watch the sunset in Islamorada with a drink in hand, Lorelei Cabana Bar is it. Lorelei’s is one of our favorite bars in the Florida Keys.

The laid-back vibe at Lorelei is the best way to close out a fantastic day in the Florida Keys. Arrive for happy hour (4-6 pm) and stay for the glorious colors that light the sky as the sun goes down. Nightly live music is an added bonus that will put you in the mood.

Lorelei has the food thing covered. They’re open all day, serving breakfast, lunch, and dinner. So, no matter what time you get there, they’ll have something to fill your tummy.

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• Address: Mile Marker 82 Bayside, Islamorada, FL

2. Holiday Isle Tiki Bar

At Holiday Isle Tiki Bar, you’ll really feel like you’re in paradise. You’ll immediately feel the tiki bar vibe with thatched roofs you can’t miss. Live music and fire pits overlooking the water take the island feel to the max.

For food, Holiday Isle has everything from fish tacos to cheeseburgers. But what about the drinks? They’re single-handedly the best part of the Holiday Isle Tiki Bar. No joke, for over 50 years, these tiki drinks have attracted visitors and locals alike.

The major claim to fame is that the original Rum Runner was created at the Holiday Isle Tiki Bar, honoring the days when Islamorada was a key point for liquor smugglers in the early 1900s.

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• Address: 84001 Overseas Highway, Islamorada

3. Florida Keys Brewing Company

The Florida Keys Brewing Company (FKBC) serves up tasty beers. All made right here in Islamorada. FKBC Tasting Room & Beer Garden is the best place to chill out and enjoy a Florida Keys beer.

There are 20 different FKBC beers on tap in the Tasting Room. So, you can taste each one and then fill a pint or growler with the one that hits the spot.

There’s always something happening at the FKBC Beer Garden. On any given day, you’ll find live music or even scavenger hunts taking place.

FKBC is kid and pet friendly. So bring the whole family for fun in the Beer Garden.

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• Address: 81611 Old Highway, Islamorada

4. Hog Heaven Sports Bar and Grill

What is it like to be a hog in heaven? You’ll have just about anything your little heart desires. So, what does that mean at the Hog Heaven Sports Bar and Grill? You’ll have it all.

First, the food and drink. This place offers it all – no jokes. With just about the longest list of things to eat in Islamorada, you’re sure to find what you’re craving.

And, of course, they serve the best BBQ around. Order it as your main meal, or add any of the succulent meats like pulled pork or brisket to your entree.

You’ll be a hog in heaven with the drinks too. The array of cocktails, frozen drinks, beers, and wines will get you your drink of choice.

The atmosphere also gives you everything you’d want. Choose a seat inside or out on the dock. Tons of TVs mean you can watch the game, and there’s even live music most nights to set the mood.

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• Address:  85361 Overseas Highway, Islamorada

5. The Bug Pub

Nestled in the Rain Barrel Village, The Bug Pub should not be missed. Something you can’t miss is Betsy, the giant lobster out front. Missing claws, Floridian lobsters are nicknamed “bugs.”

So, Betsy, the Bug is a perfect mascot for Rain Barrel Village and the Bug Pub. The Rain Barrel Village is a community of artists. Here, visitors can buy art and souvenirs alike. Make sure to put it on your things to do in Islamorada itinerary!

The Bug Pub and the Lobster Shack on site will get you what you need in the way of food and drinks. The menu is appropriately small, just like the pub, but their drink list is seriously long for such a small place.

The Bug Pub is known for its frozen cocktails served in a fresh pineapple cup. Check out their Coladas, wine slushies, or frojito. As for beers, they specialize in local and craft. But not to worry, they also have the staples we love in any good old American bar.

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• Address: 86700 Overseas Highway, Islamorada

6. Mile Marker 88

The first bar we ever visited in Islamorada was Mile Marker 88. It has changed over the years, and now it is super popular, and the prices have increased. They don’t have happy hour specials, but they have a great spot on the beach and a great place to catch the sunset.

If you do come for the sunset, make sure to come at least an hour before. Mile Maker 88 for sunset gets really busy. By the time you get your drink, the sun will have set!

They do offer dinner, but we have never eaten dinner here (only snacks) as the prices are higher than other restaurants in the area. Make sure to check out our best restaurants in Islamorada for some of our favorite places.

7. The Oceanview Inn & Sports Pub

The Oceanview Inn & Sports Pub is the place to watch football with a cold one in Islamorada.

The owners are former NFL players Gary Dunn of the Pittsburgh Steelers and Dennis Harris of the LA Rams. So, of course, it’s decked out with tons of TVs to catch the game. NFL Sundays and Monday Night Football are staples at the OV. Making it the ultimate place to grab a beer and watch the game.

The food is solid and has what you’d want when watching the game. From wings to burgers, you’re set. And, of course, they’ve got all the drinks you desire.

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• Address: 84500 Overseas Highway, Islamorada