201 Duval St
Key West, FL 33040

(305) 294-5717

Sloppy Joe’s Bar Editor’s Choice: Top Key West Bars

Sloppy Joe’s Bar, a true Key West legend, has been a cornerstone of the island’s vibrant history and nightlife since its establishment on the very day Prohibition was repealed in 1933 making it on of the top choices for Key West Bars. Originally located on Greene Street, this iconic watering hole famously moved to its current prominent spot on the corner of Duval and Greene streets in 1937, with patrons famously carrying their drinks and furniture down the block to ensure the party never stopped.

Beyond its lively atmosphere of live music, dancing, and frosty cocktails, Sloppy Joe’s is most renowned for its deep connection to Ernest Hemingway, who was a devoted regular and close friend of the original owner, Joe Russell. The bar is a living museum of Hemingway memorabilia, photos, and artifacts, and continues to host the annual Hemingway Look-Alike Contest, drawing “Papas” from around the world. It’s a place where history, revelry, and Key West’s unique, free-spirited character converge, offering an unforgettable experience for both locals and visitors.

508 Fleming St
Key West, FL 33040

(305) 294-2600

The Roost Editor’s Choice: Top Key West Bars

The Roost is a sophisticated and intimate wine, beer, and spirits shop that doubles as a cozy tasting room. Far from the boisterous bar scene, The Roost offers a curated selection of fine wines, craft beers, and unique spirits, making it a destination for those seeking quality and a more relaxed atmosphere. The knowledgeable staff are passionate about their offerings and are happy to guide patrons through their extensive collection, whether for a purchase to take home or to enjoy on-site.

With its inviting ambiance, often featuring soft lighting and comfortable seating, The Roost provides a perfect setting for a quiet evening, a thoughtful conversation, or simply a delightful exploration of beverages in the heart of Key West which makes it a top choice for Key West Bars.

• Fat Tuesday Key West (Duval Street):
  • 305 Duval St
    Key West, FL 33040
  • (305) 296-9373
• Fat Tuesday Key West (Front Street):
  • 431 Front St
    Key West, FL 33040

Fat Tuesday Editor’s Choice: Top Key West Bars

Fat Tuesday in Key West is a quintessential stop for anyone looking to cool down and get into the festive spirit with a refreshing, vibrant frozen concoction. With not one, but two convenient locations on both Duval Street and Front Street, this outpost of the famous New Orleans-inspired chain is all about fun, flavor, and an instant party vibe.

The atmosphere is consistently lively and upbeat, often featuring pumping music that encourages dancing and good times. Patrons flock to its signature rows of brightly colored slushy machines, offering an extensive menu of daiquiris and frozen drinks that pack a punch. It’s the perfect spot to grab a massive, sweet, and icy beverage to sip while strolling down Duval or to kick-start a night of revelry, embodying the carefree, indulgent side of Key West’s nightlife making it another top Key West Bars.

1117 Duval St
Key West, FL 33040

(305) 296-2680

The Rum Bar

The Rum Bar, nestled within the historic Speakeasy Inn on Duval Street, is a true connoisseur’s haven, a more refined and intimate escape from the boisterous energy of the main strip. This cozy, dimly lit establishment is dedicated to the art and history of rum, boasting an astonishing collection of over 250 different varieties from around the globe, making it a pilgrimage site for enthusiasts.

The knowledgeable bartenders are passionate guides, eager to share their expertise and craft bespoke cocktails that highlight the nuances of each spirit. With its exposed brick, comfortable seating, and a small, inviting outdoor patio, The Rum Bar cultivates a sophisticated yet relaxed atmosphere, perfect for savoring complex flavors, engaging in quiet conversation, and truly appreciating the diverse world of rum in an authentic Key West setting.

601 Whitehead St
Key West, FL 33040

(305) 294-6133

The Green Parrot

The Green Parrot Bar is a legendary Key West institution, standing as a vibrant testament to the island’s quirky, laid-back charm since 1890. Eschewing the polished glitz of some Duval Street spots, the Parrot embraces its dive bar roots, offering an authentic “sunny place for shady people” vibe that instantly puts visitors at ease. Its open-air setting and worn-in interiors, adorned with an eclectic mix of local art, historical photos, and, of course, parrot paraphernalia, create an atmosphere that feels genuinely unpretentious and inviting.

Famous for its consistently excellent live music, ranging from blues and funk to rock and reggae, the bar pulses with an infectious energy that often spills out onto the street. With its strong, affordable drinks, friendly local crowd, and unique character, the Green Parrot offers a true, unvarnished taste of Key West’s bohemian soul.

428 Greene St
Key West, FL 33040

(305) 294-1838

Capt Tony’s Saloon

Captain Tony’s Saloon is more than just a bar; it’s a living relic steeped in Key West’s colorful and sometimes eerie history. Housed in a building that has served as an icehouse, a morgue (with a “hanging tree” still growing through the bar!), a wireless telegraph station, a cigar factory, and a bordello, it truly has seen it all. This dimly lit, rustic establishment is famously the original location of Sloppy Joe’s, where Ernest Hemingway himself was a regular.

Today, its low ceilings are draped with thousands of ladies’ bras, its walls are adorned with quirky memorabilia, and every surface seems to tell a story. It’s a place where history and legend intertwine, with live music often filling the air and a genuine, unpretentious atmosphere inviting locals and visitors alike to pull up a stool (some famously painted with the names of celebrities) and soak in the raw, authentic spirit of old Key West.

124 Duval St
Key West, FL 33040

(305) 294-8507.

Smallest Bar in Key West

Tucked away on a quaint Duval Street alley, the aptly named Smallest Bar in Key West is a charming and quirky gem that lives up to its moniker. This minuscule establishment, little more than a window with a few stools, offers an intimate and highly memorable drinking experience. Despite its compact size, it boasts a surprisingly robust selection of libations, with a particular fame for its potent and delicious Key Lime Pie shots, a must-try for any visitor.

The limited space fosters a friendly, chatty atmosphere, often leading to impromptu conversations and shared laughs with fellow patrons and the quick-witted bartenders. It’s less about expansive seating and more about the novelty, the photo opportunity, and the unique, cozy charm that makes it an essential, if fleeting, stop on any Key West bar crawl.

202 William St
Key West, FL 33040

(305) 292-9520

Schooner Wharf Bar

Schooner Wharf Bar truly embodies the spirit of “Old Key West,” standing as a beloved, open-air institution right on the Historic Seaport. This rustic, charming watering hole feels like a living postcard, with its weathered wooden decks, eclectic nautical decor, and unparalleled views of the working harbor, complete with fishing boats and majestic schooners gliding by. Known for its laid-back, unpretentious atmosphere, it draws a colorful crowd of salty locals, seasoned sailors, and curious tourists, all mingling to the rhythm of live music that flows continuously from morning till night.

Whether you’re savoring fresh seafood like peel-and-eat shrimp and conch fritters, enjoying a classic Rum Runner, or simply soaking in the quintessential island breeze, Schooner Wharf offers a genuine slice of Key West’s maritime soul, making it a place where hours can effortlessly melt into memories.

313 Duval St
Key West, FL 33040

(305) 293-0230

Hard Rock Cafe

The Hard Rock Cafe in Key West offers a distinct blend of the iconic global brand with a unique island twist. Housed within a beautiful, historic three-story Victorian-style mansion on bustling Duval Street, it transcends a typical restaurant, inviting guests to step into a vibrant museum of rock ‘n’ roll history. Inside, the walls are adorned with an impressive collection of music memorabilia, from signed guitars to legendary costumes, creating an immersive, high-energy atmosphere.

While serving up its renowned menu of authentic American cuisine – think juicy burgers, hearty ribs, and classic desserts – the Key West location also infuses local flavors, catering to both the loyal Hard Rock fans and those seeking a taste of the Keys. Adding to its intrigue, the building is rumored to be haunted by the ghost of its original owner, Robert Curry, offering a uniquely spooky element to the otherwise lively dining and entertainment experience.

525 Duval St
Key West, FL 33040

(305) 294-7674

Willie T’s

Willie T’s is a true Key West icon, an open-air oasis right in the heart of Duval Street’s lively bustle. What immediately strikes visitors is the extraordinary “dollar bill decor” – thousands upon thousands of signed dollar bills stapled to nearly every surface, creating a unique, ever-evolving tapestry of global visitors.

This vibrant backdrop perfectly complements the bar’s infectious energy, driven by continuous live music from morning until late night, often spilling out onto the sidewalk and inviting passersby to join the party. Renowned for its signature “Mo-He-Toes” mojitos and a rotating menu of tempting drink specials, Willie T’s also serves up a diverse array of island-inspired dishes, from fresh seafood to gourmet pizzas, ensuring that whether you’re seeking a lively lunch, a festive dinner, or simply a refreshing tropical drink, you’re guaranteed a quintessential Key West experience.

202 Duval St
Key West, FL 33040

(305) 296-489

Rick’s Bar

Rick’s Bar, officially part of the larger Rick’s & Durty Harry’s Entertainment Complex, is a high-energy cornerstone of Key West’s legendary Duval Street nightlife. It’s not just one bar, but a multi-faceted playground designed for every kind of party-goer. Downstairs, you’ll find the original Rick’s, which transforms from a lively spot for live music during the day into a booming karaoke bar by night, inviting revelers to unleash their inner rock star.

Upstairs, the vibe shifts to a full-on dance club, boasting Key West’s largest dance floor, a state-of-the-art laser and light show, and pulsating beats from a live DJ, with a scenic balcony offering prime views of the Duval Street action. With numerous distinct bars scattered throughout the complex, including specialty cocktail spots and even a gentlemen’s club, Rick’s truly embodies the “eight famous bars, one awesome night” slogan, providing an unforgettable, dynamic, and often wild Key West experience.

400 Front St
Key West, FL 33040

(305) 296-4222

Hog’s Breath Saloon

Step into the raucous, no-frills embrace of Hog’s Breath Saloon, where the air hums with live music and the clinking of glasses. This iconic Key West institution, famously declaring “Hog’s Breath is Better Than No Breath At All,” offers an authentic slice of island life. Its open-air setting, often spilling out onto the sidewalk, invites a lively mix of sun-kissed tourists and seasoned locals to gather under the swaying palms.

Inside, rustic wooden interiors are adorned with eclectic nautical memorabilia and the bar’s signature hog imagery, creating a laid-back, unpretentious vibe. From frosty beers to tropical cocktails, patrons unwind to the sounds of talented bands, making it a quintessential stop for anyone seeking a true taste of Key West’s legendary revelry.