Live Music

Music is part of the rhythm of life in The Florida Keys & Key West. From waterfront tiki bars and open-air patios to intimate lounges and lively stages, live music drifts through the islands nearly every night of the week. Local bands, touring acts, and talented solo performers keep the soundtrack going with everything from reggae and rock to jazz, country, and island-inspired favorites. Grab a drink, watch the sunset, and settle in. The next great song is probably starting somewhere nearby.

Key West

Captain Tony's Saloon

Captain Tony’s Saloon is a historic Key West dive bar famous for its colorful past, live music, and legendary visitors like Ernest Hemingway and Jimmy Buffett.

Islamorada

Hog Heaven Sports Bar and Grill

Hog Heaven Sports Bar & Grill in Islamorada serves hearty smoked BBQ, fresh seafood, and dairy-free late-night fun just off the Overseas Highway.

Key West

The Alamo Key West

The Alamo Key West is a laid-back local bar known for its friendly atmosphere, cold drinks, and classic island charm.

The Lower Keys

Mangrove Mama's

Mangrove Mama’s — beloved seafood & steakhouse in Sugarloaf Key where Island-style flavors meet a laid-back Florida Keys vibe.

Islamorada

Tiki Bar at Three Waters Resort & Marina

The Tiki Bar at Three Waters Resort in Islamorada offers tropical cocktails, fresh bites, and stunning oceanfront views in a true island paradise.

Islamorada

Founders Park

45-acre recreation park in Islamorada with beach, pool, sports & playgrounds.

Key West

Key West Theater

The Key West Theater — performing arts & live events in Key West, where historic charm meets world-class entertainment.

Islamorada

Florida Keys Brewing Co.

Florida Keys Brewing Co. is the Upper Keys’ first microbrewery, serving award-winning craft beers in a vibrant beer garden and taproom located in Islamorada’s Morada Way Arts District—perfect for beer lovers and locals alike. Also offers a vacation rental.

Marathon

Skipjack Resort and Marina

Relax at Skipjack Resort & Marina in the Florida Keys—luxury suites, marina, pool, and fresh seafood!

The Lower Keys

Boondocks Grille and Draft House

Boondocks Grille & Draft House is a lively waterfront restaurant and tiki bar in Ramrod Key, offering fresh seafood, burgers, live music, and the only 18-hole mini-golf course in the Florida Keys.

Key West

Pickles Pub's Sandbar

Pickles Pub’s Sandbar — lively sports bar in Key West with 40+ TVs, late-night eats and poured-in-pub fun.

Key Largo

Jimmy Johnson's Big Chill

Waterfront dining & live music 7 nights a week at Key Largo’s bayside hotspot.

Key West

Hard Rock Café

Hard Rock Cafe Key West on Duval Street blends American comfort food with rock-and-roll memorabilia and island energy.

Key Largo

Gilbert's Resort

Gilbert’s Resort & Marina is a laid-back waterfront resort in Key Largo, featuring waterfront rooms, a private beach, and the Keys’ largest tiki bar with live music and dining.