Top 5 Bars in Islamorada

Islamorada isn’t just the Sportfishing Capital of the World - it’s also home to some of the most iconic bars in the Florida Keys. Whether you’re here to cast a line or kick back with a cold drink by the water, these bars deliver sunset views, live music, and that signature laid-back Keys vibe. Here are the top 5 bars in Islamorada to check out on your next trip.

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5. The OceanView Inn & Sports Pub (OV)

Local Institution with Live Music

• 📍 MM 84.5, Near Whale Harbor
• 🏈 Sports bar inside, live music and pool outside
• 🎶 Known for Wednesday “Flip Night” – flip a coin for free drinks
• 🐟 Order the mahi sandwich and chat with locals
• 📝 Tip: Owned by former NFL player Gary Dunn, this is one of the last great old Keys bars still standing

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4. Florida Keys Brewing Co. (FKBC)

Island Brews in the Beer Garden

• 📍 Morada Way Arts District
• 🍺 First microbrewery in the Upper Keys
• 🎨 Colorful taproom + tropical beer garden
• 🍻 Try the Hibiscus Kolsch or Sunset Ale
• 🎸 Live music, food trucks, and laid-back island vibes
• 📝 Tip: You can BYO-catch and have it cooked next door while you sip

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3. Hog Heaven Sports Bar & Grill

Late-Night Dockside Hangout

• 📍 Bayside, MM 85
• 📺 Casual sports bar by day, party bar after dark
• 🎶 Live music or DJs most nights, open late (till 2 AM or later)
• 🛥️ Dock-and-dine option for boaters
• 🍖 Try the hog wings and conch fritters
• 📝 Tip: One of the only spots in Islamorada that stays open late - popular with locals and fishing crews

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2. Holiday Isle Tiki Bar

Home of the Original Rum Runner

• 📍 At Postcard Inn (MM 84), Oceanfront
• 🍹 Birthplace of the Rum Runner (invented here in 1972)
• 🌴 Retro tiki vibes with carvings, neon, and thatched roofs
• 🎉 Known as a laid-back beach bar by day, party spot by night
• 📝 Tip: Order your Rum Runner frozen, and soak up the ocean breeze from the open-air bar

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1. Lorelei Restaurant & Cabana Bar

Sunsets, Live Music & Sand Underfoot

• 📍 Bayside, MM 82
• 🌅 Famous for nightly sunset celebrations with live music
• 🐟 Great for fish baskets, “cheeseburgers in paradise,” and casual beach vibes
• 🐾 Dog-friendly, ultra-casual, and always lively
• 📝 Tip: Grab a table early - this is the place to watch the sun go down in Islamorada

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🧭 Final Word

If you're wondering where to grab a drink in Islamorada, these spots cover all the bases - from beachfront sunset parties to hidden local dives. Add these bars to your itinerary for an authentic, unfussy taste of the Upper Keys.