We know how it goes. When you’re visiting the Florida Keys, you’ll want to play in the water a good part of the day and stay out long enough to see the setting sun ‘paint’ the sky in colors so beautiful you won’t believe your eyes. The good news is you can pair your sunset viewing with some equally spectacular nighttime fun—the Keys are filled with waterside spots that serve up great drinks and live music. But non-water-view venues also make the cut when it comes to awesome after-dark celebrations. Here’s a list of the 7 best spots to keep the good times going and the drinks flowing well into the night.


Caribbean Club in Key Largo

You don’t have to be a fan of classic movies or the locations where they were filmed to love Key Largo’s 83-year-old Caribbean Club. Yes, its exteriors appeared in the famed 1947 Bogart-Bacall movie “Key Largo” and, more recently, in the Netflix series Bloodline. But that’s because it had—and still has—so much going for it, like Old Florida chill and charm (it’s the oldest bar in the Upper Keys) and an awesome bayside location.

Soak up the movie memorabilia, sit outside at a picnic table, sip a beer or long-pour cocktail and lend a buzz to your sunset view, all while listening to a live band perform—depending on the group, you’ll hear everything from outlaw country and southern rock to high-energy rock and pop and dance music.


Morada Bay in Islamorada

Morada Bay is a bayside retreat where you can indulge your hunger for delicious food, drink, and dancing at their monthly Full Moon event, held right on the beach. On the dining front, you have two excellent options: Pierre’s Restaurant, featuring French Fusion cuisine with some global touches, and The Beach Café & Bar, serving a blend of Caribbean and American dishes.

Pierre’s shares its beachside, white colonial-style plantation-style house, which is full of beautiful design touches (hello Moroccan, Indian and African décor and palms swaying in the breeze!), with The Green Flash Lounge. Food is served on the second floor, drinks on the first. Dine and sip on the verandas if you want an amazing side of sunset with your meal or drink.

The Beach Café offers outdoor dining on colorful tropical tables set on the sands alongside shimmering blue waters, as well as indoor service that surrounds you with Hawaiian and Californian surfer memorabilia. Dig into creative local seafood- and produce-based dishes and accompany them with choice wines and signature bar drinks.

If you come for the monthly Full Moon event, you’ll get live music on the beach and can dance the night away to DJ music at the Beach Café and the Green Flash Lounge. This just may be the best party you ever attend!


OceanView Inn & Sports Pub in Islamorada

Head to the OceanView Inn & Sports Pub, owned by former Pittsburgh Steelers standout Gary Dunn and former Los Angeles Rams All-Pro Dennis Harrah, for outdoor seating around a poolside BBQ pit with lovely Gulf views in the distance. The colorful Adirondack chairs around the atmospheric flames are irresistible, and they’re positioned right in front of the open-air but oh-so-cozy Pub, lovingly known by locals and regulars as The OV.

There, you can play pool, watch sports, down your favorite drink and grab a bite (the type of fare here: shrimp, dolphin, beef burgers, and sandwiches). But come on Monday to layer in karaoke, on Thursday to add in steak, and on Sunday to amp up the fun with live music. Chillax? Not!


Kiki’s Sandbar Bar & Grille in Little Torch Key

Picture a large, thatched Tiki-style hut on stilts with broad verandas overlooking a sandy beach and the turquoise waters of the South Pine Channel. That’s what Kiki’s Sandbar Bar & Grille is like. Whether you pull up by boat or kayak (yep, it’s that close to the water) or come by car or motorcycle, the bull sharks swimming around the pier, numerous craft beers, and delicious sandwiches and tacos made with fresh-caught fish and seafood will be waiting for you.

Take a seat inside or out, then dig in. Consider starting with Kiki’s Ahi Tuna Nachos and ending with the Famous Key Lime Pie. The live music just makes everything that much more tasty. Vacay away….


My New Joint in Cudjoe Key

In the mood for light bites, drinks, and tunes? Cudjoe Key has a made-to-order spot that garners raves: a laid-back cocktail lounge, tapas bar, and live music venue called My New Joint. Perched on top of Square Grouper Bar and Grill (a delicious restaurant in its own right), My New Joint serves dishes that pair perfectly with a robust roster of creative cocktails (and wines and 170 different bottled beers). Mouthwatering things like empanadas and seafood stews. ‘Course, they also have yummy sandwiches, sliders, tacos, and salads.

Don’t know ‘bout you, but we’d go for whatever the raw bar is serving that day (freshly shucked oysters, perhaps), some roasted veggies (e.g., Charred Brussels Sprouts or Roasted Radishes) and a mouthwatering dessert, say, some Warm Mini Donuts or a Fried Banana Split (reminder: the name doesn’t mean you have to split it with anyone).


Brass Monkey in Marathon

Brass Monkey, a local (and from the outside, very unassuming) institution, is one of the top dive bars around. Whether you make the Monkey your happy place for Happy Hour or exciting nighttime action that lasts straight through to 4:00 a.m., you’re sure to get more than you bargained for. Inexpensive drinks, downhome food like country fried steak and mashed potatoes, pool and friendly service are just the beginning. Keys residents have been flocking here for more than 30 years to listen and dance to the live talent’s music.

Local legend Freddie Bye has been playing rock classics (and a mean guitar!) with super impressive bands for several decades. Over the years, some big names have taken the stage, too (e.g., Gregg Allman in the early 1980s, E-Street saxophonist Clarence Clemons and Backstreet Boy Nick Carter in the early 2000s).

If you visit in July, don’t miss the Christmas and New Year’s in July parties (hey, there’s nothing like experiencing some winter wonder on a sizzling summer night—or, in this case, two searing nights). We wouldn’t be at all surprised if these fests become ‘holiday’ traditions for you ‘cause basic greatness has a way of sinking its hooks into you.

If you do, the staff at this watering hole will become part of those traditions—they tend to stay put.


Sunset Grille & Raw Bar in Marathon

Finding the Sunset Grille & Raw Bar is easy—it’s located at the foot of the new 7 Mile Bridge on the Atlantic Ocean. But you know what else stands out at this tiki hut-style restaurant and bar? The ginormous pool, which borders a wide oceanfront beach where you can down a drink; the robust breakfasts that include a Bloody Mary Bar (in our opinion, a very viable way to extend nighttime festivities); live music every night; and excellent food. Four most delicious must-tries on the varied yet fish-centric menu (which also includes sushi): Clam Chowder, Hogfish Martinique, Cobb Salad and the Chocolate Bomb.

Sunday Funday, a longstanding weekly event here, is a next-level weekend party that goes from 1-5 p.m. Dance to the beats of a poolside DJ, play games and win prizes, and enjoy a bunch of special eats.

As for that mind-blowing sunset you’ll see? Just think of it as a perfect sendoff—yeah?