The Florida Keys stretch 125 miles southwest toward Key West, and if there is a more concentrated collection of legendary beach bars anywhere in the United States, the Beach Bar Bum has not found it. From the Caribbean Club in Key Largo — forever immortalized by Bogart and Bacall’s Key Largo — to the neon-soaked chaos of Duval Street in Key West, the Keys deliver a beach bar experience unlike anywhere else in America.
We happily present some of the best beach bars in the Florida Keys, from Key Largo to Key West.
Caribbean Club at MM 104 is a genuine historic landmark — the exterior was used filming Key Largo with Bogart and Bacall. Gilbert’s Tiki Bar brings cold beers and waterfront warmth. Lorelei Restaurant & Cabana Bar in Islamorada is one of the finest sunset bars in the Keys — right on the bay with a floating live music stage. Morada Bay Beach Cafe, Marker 88, Hog Heaven, and Islamorada Fish Company fill out a stretch where every mile marker has something worth stopping for.
Island Fish Company Tiki Bar, Burdines Waterfront Chiki Tiki Bar, Sunset Grille & Raw Bar, Sparky’s Landing, and TJ’s Tiki Bar make Marathon a legitimate destination. Do not drive past No Name Pub on Big Pine Key without stopping — dollar bills papered on every surface, cold beer, and one of the most beloved dive bars in the entire Keys.
Sloppy Joe’s at 201 Duval is where Hemingway drank and the legend began in 1933. Captain Tony’s Saloon is the original 1851 location — the oldest bar building in Florida. Schooner Wharf Bar on the Historic Seaport is the most atmospheric bar in the Keys. Louie’s Backyard Afterdeck Bar delivers arguably the most beautiful outdoor bar setting in Florida. Sunset Pier, Lagerheads, The Smallest Bar, and Southernmost Beach Cafe complete a Key West lineup with no equal in the US.
The Overseas Highway (US-1) is your bible down here — it connects all the Keys from MM 126 at Florida City to MM 0 at Key West, and most bars list their Mile Marker as their address because nothing else matters. Follow the numbers, stop often.
Happy hour runs early (3-6 PM is standard) and sunset on the bay side isn’t just a time of day — it’s a religion. Missing it is not an option.
Fly into Miami or Fort Lauderdale and plan at least 3-4 days. Key West alone is worth 2 nights. A convertible is not required but if you show up in a minivan, the Beach Bar Bum is not responsible for your shame.