Best Bars In The Florida Keys

Bars, al fresco drinking, and tropical cocktails are all part of Floridian foodie culture, from sandy beach bars along the panhandle to the abundant nightlife hot spots in Miami Beach. But don't overlook the Florida Keys, an epic waterside road trip to the southern tip of the state that's home to a lively and endearingly quirky bar culture all its own.

From an edible standpoint, when most people think of the Conch Republic (the Keys' nickname after they declared themselves a micronation in 1982, according to the Conch Republic site), they imagine key lime pie — and maybe conch, coconut shrimp, and other tropical bites. But from a boozy standpoint, there's much more to the Keys than casual, frills-free watering holes. While this tropical archipelago is known for its laid-back charm, drinking options span the spectrum — from quintessential beach bars and leisurely dockside lounges to cocktail nooks, poolside hotel bars, rustic pubs, and everything in between. For a singular sip of Florida, check out these great bars in the Florida Keys.

What began as a general store and tackle shop back in 1931, evolved into a funky and eclectic tavern that has been a Keys institution for generations. No Name Pub is now a go-to pitstop for casual food and drink on any Keys-hopping road trip. The colorful patio-clad bar features local requisites like smoked fish dip, coconut shrimp, and conch fritters, alongside burgers, conch chowder, pizza, and a whole range of potable pleasures.

To drink, No Name Pub offers a laundry list of quenching crowd-pleasers: beer, seltzer, wine, sangria, and piña coladas among them. As refreshing and straightforward as the drinks are, folks flock here for the ambience — all the edible and drinkable comforts are served up in an adorably timeworn space decorated with lobster traps, dollar bills plastered all over the ceiling, and thatched roof huts strung up with twinkling lights.

Come for the local Florida beer and the key lime pie punch at this legacy bar, and linger for the larger-than-life sunsets and live music on the waterfront palm tree-lined patio. Open since 1938, Caribbean Club is an enduring dive bar that feels like a vintage Florida watering hole, made famous by its appearance in the film "Key Largo," starring Humphrey Bogart and Lauren Bacall. And if Caribbean Club is good enough for Bogart and Bacall, it's good enough for a stopover while in the Florida Keys.

This classic bar looks and feels how it probably did when they filmed the 1948 movie, from its cash-only policy and cheap drinks to its pool table and whimsically haphazard decor, including a fireplace, fishing nets, fake dolphins, and a somewhat eery life-sized Humphrey Bogart figure. The only significant modern-day touches at this open-air bar are the karaoke nights and live music on the waterfront stage.

Marked by a huge mermaid sign, the Lorelei Restaurant & Cabana Bar is an impossible-to-miss Islamorada icon and a mainstay for all-day dining, nightly live music, happy hour, and tropical tipples on the sand. Much of the seating here is on a massive covered dock that's literally right on the water, ensuring the sunset views are as epic as possible.

While the restaurant portion of this waterside complex offers sterling seafood — including Floridian requisites like peel-and-eat shrimp, stone crab chowder, and blackened fish sandwiches — the cute and cozy cabana bar is a great spot to hunker down with a refreshing drink off the enormous beverage list. In addition to beer and wine, the spotlight here is on their well-made frozen drinks (rum runners, piña coladas, strawberry daiquiris, etc.) and other tropical rum-focused libations, like the Lor-e-Mai-Tai, Bahama Mama, Planters Punch, and Tipsy Mermaid.

When it comes to imbibing on the Florida Keys, getting tipsy usually involves a fair amount of rum, margaritas, and ice-cold beer. Which is what makes Islamorada Wine Co. such a welcome rarity. The cozy, comfy wine bar on Islamorada is all about wine — both New World and Old, with wine-friendly snacks and shareable plates to round it all out.

Compared to many beachfront bars on the Keys, Islamorada Wine Co. is relatively new (opened in October of 2020), and offers wine tastings, pours, and bottles alongside charcuterie platters, Sunday brunch, and wine-paired bites like Champagne mac and cheese, prosciutto-wrapped dates, and caprese salads. The space itself is also a departure from typical Keys bars — it's a far cry from the boisterous and clamorous beach hangouts. This place is intimate and charming — it feels like you're visiting a good friend's house for a wine-soaked dinner party.  

Tucked away in a nondescript nook of Safe Harbor on Stock Island, Hogfish Bar & Grill is mostly known for its namesake hogfish sandwich and other hogfish-based delicacies, utilizing a local underrated specialty (via Key Largo Fisheries) that's known for its mild flavor and flaky texture (via Take Me Fishing), with hints of scallop and lobster (which makes sense, since hogfish eat mostly crustaceans). It's a true in-the-know spot for locals and gets a good crowd going on the weekends. 

However, it isn't all about hogfish here. Don't overlook the bar component of this rustic, eclectic haunt, which is destination-worthy in and of itself. It's decidedly low-key (don't expect white tablecloth service here) and a reliable go-to for tropical mixed drinks and cheap beer. The overall indoor-outdoor vibe — bedecked with all manner of nautical knickknacks, an outdoor patio bar, and harbor-side picnic tables — give it that quintessential feel of an old Florida bar endearingly preserved in time.

Tiki cocktails and the Keys go together like coconut and shrimp, and if there's one tiki standby you need to visit, you might as well make it the largest tiki bar in the area. Boondocks Grille and Draft House is a sprawling bar, restaurant, and full-fledged miniature golf course, with a vast pet-friendly patio, a live music stage, and a tiki-style thatched roof that'll transport you right to the Caribbean.

The something-for-everyone and come-as-you-are vibe of Boondocks is apparent in its expansive comfort food menu of pizzas, seafood, and burgers. There's even a dedicated pet menu with dog treats like "woofer burgers," bacon strips, and French poodle fries. The drink menu is as enormous as the space, with ample draft and bottled beer, wine, frozen cocktails, a Champagne section, and house tiki specialties like mai tais, painkillers, and category 5 hurricanes — as the name suggests, they're extra strong, so slurp with caution. For something a tad daintier, try the signature key lime martini with Liquor 43, Captain Morgan, ice cream, orange juice, and lime juice.

The oldest bar in Florida (via Atlas Obscura) is well worth a visit, and the endearingly rickety Capt. Tony's Saloon on Key West does not disappoint. Originally built as an icehouse in 1851, the bar changed names and hands over the years, all while becoming a fixture for famous barflies like Ernest Hemingway and Jimmy Buffet. Its legacy has endured the test of time, too.

The bar is named after Captain Tony, a fishing boat captain and a former mayor of Key West, and it's retained all of its lore and luster. An old-timey seaside saloon, this is the kind of cheeky bar festooned with business cards, dollar bills, and bras all over the walls, while foosball, pool, and live music provide entertainment. Quirkily enough, there's also a tree growing right in the middle of the bar where people congregate in the clamorous space for rum punch, tequila shots, hard seltzers, and beer.

A decidedly modern addition to Key West's storied drinking scene, Waterfront Brewery is a lofty two-level brewery and beer bar in a warehouse-style space equipped with pool tables, a dockside patio, and plenty of sports-tuned TVs. Open since 2015, the bar is located right on the historic Key West Bight marina, with oceanfront patio views for days. The brewery puts beer front and center, while also offering rum-centric cocktails, wine, and a full Floridian food menu of fish dip, scallops sautéed in rum, conch chowder, Caribbean skirt steak, and key lime pie.

Draft beer options at the brewery rotate seasonally and run the gamut, from tried-and-true styles to crafty innovations. Examples include the tropical 35a IPA, the Bigger Boat White pilsner, and the Island Life Lager. There's even a Key Lime Pie beer (via Beer Advocate), a lager swimming in notes of key lime juice, marshmallow, vanilla, and graham crackers.

Key West has long been known as a haven for queer culture and nightlife (via The Advocate), and 801 Bourbon Bar is at the epicenter of it all. The pink-hued, multi-story bar on Duval Street plays a lively role in Key West's bar and restaurant culture as a bastion for late-night dancing (open until 4 a.m.!), karaoke, and over-the-top drag shows.

While the entertainment — and the clubby atmosphere — is the star attraction at 801 Bourbon Bar, it's generally just a great place to go for a drink with a side of drag bingo. In addition to the lively event space with a stage for the saloon's countless shows, there's a sexy neon-lit bar that serves a rotating roster of craft beer on tap and bourbon-focused mixed drinks in a quieter and more intimate space (though the bar is fully stocked to pour you whatever you'd like).

As fun as it is to stay out clubbing and bar-hopping until the wee hours, in true Key West fashion, sometimes you just need a leisurely mimosa by a shaded pool. For a break from the local nightlife fray, hole up at Isabel's, a chic poolside hotel bar at the Kimpton Lighthouse Hotel. More of a place to lounge with a book than do shots on a dance floor, it's a nice alternative to all the raucous hoopla on Duval and serves as a peaceful day drinking destination.

Bedecked like a bougie bungalow, this pastoral tree-draped hideaway offers a more refined take on pool drinks, taking the time to craft well-balanced mojitos, elderflower spritzes, hurricanes, mai tais, and Key West coolers made with vodka, cranberry, coconut water, and orange. There's also a curated selection of beer, seltzer, bubbly, and wine, with snacks like hummus, chips and salsa, and fish dip.

Out of the entire archipelago, Key West is the destination best known for eccentricity and whimsy. No bar personifies that notion quite like General Horseplay, an eclectic and boisterous cocktail bar with live music, dancing, playful drinks, and a dessert called cupcake sushi — a chocolate-y dessert that features a cupcake shaped like sushi and drizzled with Crème de Noyaux strawberry sauce. It also comes in cocktail form.

This is one of the foremost destinations on Key West for unique cocktails, including spiced banana daiquiris, bourbon- and watermelon-infused Murricanes, and Cornucoparitas made with tequila, apple-cinnamon reduction, lime, papaya, and white tea. There's also a selection of cocktails made with rare, high-end spirits, including an old fashioned anchored by Woodford Reserve Master's Collection bourbon. For something a bit more casual, head to the Back Bar, an outdoor area with lawn games, live music, draft beer, and more straightforward cocktails like rum punch and margaritas.