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.

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