The best bars in Key Largo sit bayside along the Overseas Highway, where the sunset over Florida Bay is the main event and a band usually starts as it goes down. About 20 miles south, Islamorada adds tiki bars, two breweries and a late night stage. Music nights below come from each venue, and venues in our venue directory link to their full profiles.
Quick Picks
- Best for history: Caribbean Club, Key Largo.
- Best for a band every night: Lorelei Restaurant and Cabana Bar, Islamorada.
- Best for a classic tiki bar: World Famous Tiki Bar at Three Waters, Islamorada.
- Best for craft beer and local bands: Florida Keys Brewing Co, Islamorada.
- Best for staying out late: Hog Heaven Sports Bar and Grill, Islamorada.
- Best for sunset dinner with music: Snooks Bayside, Key Largo.
Bars in Key Largo
Caribbean Club
Open since 1938 and run by the Whitehurst family since 1963, the Caribbean Club calls itself the oldest bar in the Upper Keys and the place where the movie Key Largo was filmed. It sits at 104080 Overseas Hwy, Key Largo, on Florida Bay, and says it has won Best Sunset in the Keys Weekly Best of the Upper Keys awards three years running. Live music runs Thursday through Sunday on a waterfront stage, with karaoke on Wednesdays. The bar opens at 7am and is cash only, with an ATM on site (get directions).
Sundowners Key Largo
A bayside restaurant at 103900 Overseas Hwy, Key Largo, Sundowners Key Largo has been open since 1985 and looks out over Florida Bay. Live music plays Thursday to Sunday from 6pm to 9pm, and the bar runs happy hour Monday to Friday from 3pm to 6pm. It suits a dinner, sunset and band night (get directions).
Jimmy Johnson’s Big Chill
Just up the highway at 104000 Overseas Hwy, Key Largo, Jimmy Johnson’s Big Chill is a bayside complex with a restaurant, tiki bar, sports bar, pizza counter and a pool with cabanas. It advertises live music every day. It is the easiest pick for a big group with mixed plans (get directions).
Snooks Bayside Restaurant and Grand Tiki Bar
At mile marker 99.5, 99470 Overseas Hwy, Key Largo, Snooks Bayside Restaurant and Grand Tiki Bar promises a water view from every seat and has three bars. Live music plays nightly from 5:30 to 9:30, with afternoon bands on weekends, and happy hour runs daily from 3pm to 5pm at all three bars (get directions).
Gilbert’s Resort Tiki Bar
At the north end of Key Largo, 107900 Overseas Hwy, Gilbert’s calls itself the first and last stop in the Keys and its tiki bar the largest in the Florida Keys. Keys Weekly readers voted its piña colada the best. Bands play classic rock, reggae, country and top 40 several nights a week, with music all weekend, and happy hour runs Monday to Friday from 4pm to 6pm (get directions).
Bars in Islamorada
Lorelei Restaurant and Cabana Bar
Look for the mermaid sign at mile marker 82 bayside, 96 Madeira Rd, Islamorada. The Lorelei Restaurant and Cabana Bar has live music seven nights a week, a sunset celebration every evening and happy hour daily from 4pm to 6pm. Posted sets often run from 5pm to 9pm. The property was put up for sale in 2026, but the restaurant stays open daily (get directions).
World Famous Tiki Bar at Three Waters
Opened in 1969 as the Holiday Isle Tiki Bar, the World Famous Tiki Bar at Three Waters says it is the first tiki bar in the Florida Keys and the place the Rum Runner was invented in the 1970s. It sits by the marina at Three Waters Resort, 84001 Overseas Hwy, Islamorada. Live music plays Thursday through Sunday from 6pm to 9pm (get directions).
Florida Keys Brewing Co
The Upper Keys’ first microbrewery pours from its tasting room and beer garden at 81611 Old Hwy, Islamorada. Florida Keys Brewing Co won Best Live Music in the Keys Weekly Best of the Upper Keys awards for the fourth straight year in 2025, plus Best Bar. The tasting room is open Monday to Saturday from 11am to 10pm and Sunday until 8pm, and the beer garden is pet and kid friendly (get directions).
Islamorada Brewery and Distillery
Open since October 2014 at 82229 Overseas Hwy, Islamorada, Islamorada Brewery and Distillery bills itself as the only brewery and distillery in the Florida Keys. It is open Sunday to Thursday from 11am to 9pm and until 10pm on Friday and Saturday, so check its Facebook events page for music before you go (get directions).
Hog Heaven Sports Bar and Grill
The Upper Keys go quiet early, and Hog Heaven, an oceanfront sports bar at 85361 Overseas Hwy, Islamorada, is where people go when they don’t want to. It has 27 TVs, billiards, indoor and outdoor bars, and happy hour Monday to Friday from 4pm to 7pm. Its band schedule has Friday and Saturday shows from 8pm to midnight, earlier sets on Sunday, Monday and Thursday, and a DJ on weekends (get directions).
Planning a Night in the Upper Keys
Everything here is on or just off US 1, the Overseas Highway, and addresses follow the mile markers: Gilbert’s is around mile 108, the Key Largo bars cluster between 99 and 104, and the Islamorada stops run from 81 to 85. Plan on a designated driver or a room near your last stop. Several of these bars have docks if you are arriving by boat.
Music is busiest Thursday through Sunday, and most bayside bands start before sunset and finish by 9pm or 10pm. A good plan is sunset at the Caribbean Club or the Lorelei, a set at a brewery or tiki bar, then Hog Heaven if you want to stay out late. If you are driving on to Key West, see our guides to Key West bars with live music and Key West nightlife. Coming down from the mainland? Our best live music in Miami guide covers the night before.
Frequently Asked Questions
What are the best bars in Key Largo?
The Caribbean Club for history and sunsets, Snooks Bayside or Sundowners for dinner with a band, and Gilbert’s for the biggest tiki bar.
What are the best bars in Islamorada?
The Lorelei for sunset and nightly bands, the World Famous Tiki Bar at Three Waters for the original Rum Runner, Florida Keys Brewing Co for craft beer and local music, and Hog Heaven for a late night.
What is Islamorada nightlife like?
Relaxed and early. Most bands play from around 5pm or 6pm to 9pm. Hog Heaven is the exception, with bands until midnight on Friday and Saturday and a DJ on weekends.
Where can I find live music in Key Largo and Islamorada tonight?
The Lorelei has music seven nights a week, Snooks Bayside plays nightly from 5:30 to 9:30, and Jimmy Johnson’s Big Chill advertises music every day.
Which tiki bars in Islamorada are worth visiting?
The World Famous Tiki Bar at Three Waters is the original, with bands Thursday through Sunday. The Lorelei’s cabana bar is the other classic.
Header photo: Baron Maddock, via Wikimedia Commons, CC BY 4.0.
