The Best Spots for a Drink at Sunset in the Middle Keys

Is there any better way to end a day of driving the Florida Keys than watching a dreamy sunset over the Gulf of Mexico, margarita in hand? Here’s our guide to the top bars and eateries in the Middle Keys where you can do just that.

Sunset Grille & Raw Bar

Sunset Grille & Raw Bar is a restaurant that has become a local favorite for its extensive sushi menu, its seafood dishes, its daily 3-6pm happy hour, and its weekly “Sunday Funday” DJ sets. Its signature Tiki hut sits right beside the ocean, so you get front-row views of the brilliant purple and orange sunset. 

Morada Bay Beach Café and Bar

Along with its own uninterrupted sunset views, Morada Bay Beach Café and Bar serves up Frommer’s-approved Caribbean-American cuisine, beachy surf and kiteboard-themed decor, and a breezy indoor-outdoor layout. Its setting, Morada Bay, is frequently recommended as one of the prettiest beaches for those making their way down the Keys.

Marker 88

Marker 88 is a casual and laid-back steak and seafood joint in Islamorada that draws locals for lunch, dinner, and Sunday brunch, as well as sundowners. Along with being quite historic, having opened in the late 1960s, it holds the unique claim of occupying one of the Keys’ few natural beaches.

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The Lorelei Restaurant and Cabana Bar

The Lorelei Restaurant and Cabana Bar pairs its sunsets with entertainment by local bands, like The Stone Crabs and Webb, Webb, and Davidson. Its combination of gorgeous scenery with delicious seafood and funky mermaid-inspired art has led to praise from publications like Travel + Leisure, Florida Rambler, and The Star Tribune.

The Island Fish Co. Restaurant & Tiki Bar

Hit up the Island Fish Co. Restaurant & Tiki Bar, home to the longest tiki bar in the Keys, for the last sunset of your Keys adventure. There’s a mercantile shop at this tropical-themed eatery, so you can purchase a souvenir to help remember your special evening.

Check out these spots and more on your next Florida Keys getaway. If you need a place to stay, browse the tempting offers at Cheeca Lodge & Spa.

Driving the Florida Keys: Everything You Need to Know

The Florida Keys are one of America’s most famous road trip destinations. Here’s what to know before you hop in your rental convertible and take on the 113-mile Overseas Highway for yourself.

Iconic eateries

You’ll be confronted with so many seafood restaurants that you won’t even want to finish making it to Key West. Hungry Tarpon, Wooden Spoon, Lazy Days Restaurant, and Mrs. Mac’s Kitchen are just a few spots known for the region’s delicious seafood, as well as hearty desserts. Fun, kitschy decor also characterizes many of these restaurants, like dollar bills, license plates, and surfing-related gear, so feast your eyes as you savor the signature conch fritters or Key-lime pie.

Iconic bars

Piña coladas and margaritas are as much a Florida Keys staple as the aforementioned seafood snacks. In the course of planning your itinerary, or simply drifting down the highway at your comfortable pace, prepare to encounter storied dive bars from Alabama Jack’s to No Name Pub (many with their own eye-catching decor). For a local beer in lieu of the requisite margarita or piña colada, try the Florida Keys Brewing Company, hosting tours and tastings.

Unexpected attractions

Prepare to see incredible attractions unlike anything you’ve seen elsewhere, like the massive Seven Mile Bridge, the Robbie’s Restaurant tarpon pier, the giant lobster sculpture at the Rain Barrel Artisan Village, and a hospital dedicated to rehabilitating rescued turtles. The History of Diving Museum is another one-of-a-kind spot, as the world’s largest collection of diving-related artifacts, like bell helmets and cameras for underwater photography.

Beautiful scenery

One of the best parts of a Keys road trip is the amazing scenery. As you make your way south, stop at Anne’s Beach, Bahia Honda State Park, and Morada Bay for soft sands and crystal-clear waters, and John Pennekamp State Park for boat rides around snorkeling spots with lush coral reefs. And don’t miss the world-famous sunsets, either: Grab a Gulf-facing seat at the Lorelei Restaurant and Cabana Bar or embark on one of the Keys Sunset Sails.

If you need a place to rest up during your Florida Keys road trip, check out the exclusive offers at Cheeca Lodge & Spa.