Key West’s Top 20 Bars: A Nightlife Adventure

Key West’s Top 20 Bars: A Nightlife Adventure

Key West’s sunset paints the sky a fiery goodbye, and neon lights beckon me into the night’s embrace. Dive bars with Hemingway’s ghost and laid-back joints thumping with live music line the streets, each a portal to a different adventure.

I can lose myself in the electric energy of Rick’s dance floor, sip secrets from hidden speakeasies, or sway under the stars to the rhythm of a local band.

This island is my playground tonight, a cocktail of vibrant energy, tropical whispers, and endless possibilities. Glass raised, I’m ready to embark on a Key West bar crawl I’ll never forget. Let’s go!

1. Sloppy Joe’s Bar

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Sloppy Joe’s Bar, an iconic establishment on Duval Street in Key West, stands as a historic watering hole synonymous with lively entertainment. Since its founding in 1933, Sloppy Joe’s has welcomed patrons with its vibrant atmosphere and live music. The bargained fame as a favourite haunt of the legendary writer Ernest Hemingway, adding to its rich history.

The interior boasts a classic pub ambiance, adorned with memorabilia and a bustling crowd. Visitors revel in the spirited performances by talented musicians, making it a must-visit destination for those seeking a taste of Key West’s lively nightlife and a glimpse into its storied past.

2. The Green Parrot Bar

The Green Parrot Bar, nestled in Key West, is an iconic and laid-back establishment renowned for its tropical ambience and vibrant live music. Since 1890, it has charmed patrons with its relaxed atmosphere and friendly staff. The bar’s exterior, adorned with whimsical signage, welcomes visitors to a haven of leisure.

Inside, the eclectic decor and a diverse crowd create a casual and inviting space. The Green Parrot is a mecca for music enthusiasts, hosting talented local and national acts across various genres. With its easygoing charm, tropical drinks, and unforgettable tunes, this bar encapsulates the essence of Key West’s unique and vibrant culture.

3. Hog’s Breath Saloon

Hog’s Breath Saloon, a beloved fixture in Key West, is renowned for its laid-back charm, live music, and iconic outdoor deck. Nestled on Duval Street, this establishment has been a local favourite since 1976. The outdoor deck, adorned with whimsical signs and surrounded by lush greenery, offers a relaxed setting for patrons to enjoy tropical drinks and live performances.

Famous for its Hog’s Breath slogan, the saloon exudes a carefree island vibe. Visitors revel in the diverse musical acts, ranging from rock to blues, making it a quintessential Key West experience. Hog’s Breath Saloon captures the spirit of the Keys with flair and flair.

4. Irish Kevin’s

Irish Kevin’s, a lively Irish pub located on Duval Street in Key West, is a spirited destination known for its energetic live performances and engaging atmosphere.

With its vibrant green exterior, the pub beckons locals and tourists alike to immerse themselves in Irish hospitality. The lively ambience is fueled by talented musicians delivering energetic sets, often encouraging sing-alongs and audience participation.

The pub’s intimate setting enhances the sense of community, creating a memorable experience for patrons. Whether enjoying traditional Irish tunes or contemporary hits, Irish Kevin’s stands out as a dynamic establishment where the spirit of Ireland meets the spirited charm of Key West.

5. Captain Tony’s Saloon

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Captain Tony’s Saloon, a historic gem in Key West, boasts a colourful past that has left an indelible mark on its character. Once the site of an icehouse, morgue, and bordello, it transformed into a beloved watering hole in 1933.

Frequented by literary legend Ernest Hemingway, the bar exudes an old-world charm with its sawdust-covered floors and eclectic memorabilia. Hemingway, a regular patron, reportedly recruited soldiers for his boat at Captain Tony’s during World War II.

The iconic tree within the bar is said to have served as the town’s hanging tree in the 19th century. With its rich history, Captain Tony’s Saloon remains a fascinating glimpse into Key West’s past.

6. Rick’s Bar

Rick’s Bar, a dynamic hotspot in Key West, stands as a multi-venue complex offering a diverse and energetic nightlife experience. Located on Duval Street, this entertainment haven comprises various bars, dance floors, and live entertainment spaces.

The complex is a bustling amalgamation of distinct venues, each catering to different tastes and moods. Whether patrons seek live music, DJ beats, or a vibrant dance floor, Rick’s Bar delivers a lively atmosphere.

The energetic ambience, coupled with its central location, makes it a go-to destination for revellers exploring Key West’s vibrant nightlife. Rick’s Bar promises a multi-faceted and unforgettable evening of entertainment.

7. Margaritaville Key West

Margaritaville Key West, inspired by the laid-back island philosophy of Jimmy Buffett, immerses visitors in a tropical oasis with a casual and carefree atmosphere. Located in the heart of Old Town Key West, this vibrant destination captures the essence of the Margaritaville lifestyle.

The venue is renowned for its signature tropical drinks, including the iconic margaritas, served in a setting adorned with beachy decor and colourful vibes. Live music often serenades patrons, enhancing the island escape experience. Margaritaville Key West invites guests to relax, unwind, and embrace the easygoing spirit of the Florida Keys, making it a must-visit for those seeking a slice of paradise.

8. The Porch

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The Porch, nestled in Key West, has carved a niche as a beloved establishment known for its craft beers, laid-back ambience, and live musical vibes. Located in the heart of Old Town, this venue offers a welcoming setting where patrons can unwind and savour a diverse selection of craft brews.

The relaxed atmosphere, coupled with friendly staff, makes it a favourite among locals and visitors alike. Live music performances enhance the overall experience, providing a perfect backdrop to enjoy a drink and good company. Whether seeking a quiet escape or a lively night out, The Porch delivers a memorable blend of craft beer and musical charm.

9. Durty Harry’s Entertainment Complex

Durty Harry’s Entertainment Complex, a vibrant destination in Key West, offers a multi-level extravaganza of entertainment. Located on Duval Street, this dynamic complex encompasses various venues, ensuring a diverse and lively nightlife experience.

With multiple bars, each exuding its charm, and spacious dance floors, Durty Harry’s caters to a spectrum of tastes. The lively atmosphere is complemented by live entertainment, ranging from bands to DJs, ensuring an unforgettable night out.

The energetic ambience, friendly crowds, and central location make Durty Harry’s a hub for revellers seeking a multifaceted and exciting evening in the heart of Key West’s vibrant entertainment scene.

10. Bourbon Street Pub

Bourbon Street Pub, situated in the heart of Key West, is a popular LGBTQ+ bar celebrated for its vibrant atmosphere and exciting themed events. This lively establishment stands as a welcoming hub for the LGBTQ+ community and allies, fostering inclusivity and diversity.

Patrons can enjoy a dynamic ambience, complete with energetic music and a friendly crowd. Bourbon Street Pub hosts an array of themed events, from drag performances to dance nights, adding a unique flair to the vibrant Key West nightlife.

11. The Rum Bar at the Speakeasy Inn

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The Rum Bar at the Speakeasy Inn, nestled in Key West, stands as a charming and historic haven for rum enthusiasts. This cosy spot exudes a nostalgic ambience with a touch of the past, as it is housed within the Speakeasy Inn, a historic landmark.

The bar’s allure lies in its extensive rum selection, showcasing a diverse array of flavours and blends. Visitors can savour the rich history of Key West while enjoying crafted rum cocktails in an intimate setting. The Rum Bar at the Speakeasy Inn provides a delightful retreat for those seeking a laid-back atmosphere and a taste of the city’s storied past.

12. Smokin’ Tuna Saloon

Smokin’ Tuna Saloon, a Key West gem, invites patrons to immerse themselves in a laid-back island experience where live music, delectable seafood, and a relaxed vibe converge. Located in Old Town, this saloon is a haven for music enthusiasts, featuring talented artists in a variety of genres.

The coastal ambience pairs perfectly with its seafood-centric menu, offering fresh catches and culinary delights. Whether enjoying a casual afternoon or a lively evening, the Smokin’ Tuna Saloon captures the essence of Key West’s easygoing spirit. With its beachy charm, live performances, and delicious fare, it stands as a quintessential destination for those seeking an authentic island experience.

13. Island Dogs Bar

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Island Dogs Bar in Key West beckons both humans and their furry friends with its unique blend of pet-friendly hospitality and vibrant island vibes. Nestled in the heart of Old Town, this welcoming bar features a tropical courtyard where patrons can enjoy craft cocktails amidst a relaxed setting.

Live music enhances the lively atmosphere, providing a soundtrack to the island experience. The pet-friendly policy adds an extra layer of charm, inviting visitors to share the joy with their four-legged companions. Island Dogs Bar seamlessly combines the warmth of a tropical retreat with the spirit of Key West, creating a delightful haven for locals and tourists alike.

14. Bagatelle

Bagatelle, situated in Key West, stands out as a stylish lounge where sophistication meets island charm. This chic establishment offers a refined atmosphere that seamlessly blends with the laid-back vibes of the Florida Keys. Known for its craft cocktails, the bar’s mixologists curate a menu that tantalizes the taste buds.

The contemporary design and upscale ambience make Bagatelle a perfect setting for socializing or enjoying a quiet evening. Whether sipping a meticulously crafted cocktail indoors or on the outdoor patio, patrons revel in the fusion of elegance and tropical allure. Bagatelle promises an exquisite and memorable experience in the heart of Key West.

15. The Bull and Whistle Bar

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The Bull and Whistle Bar, an iconic Key West destination, beckons patrons with its vibrant atmosphere, live music, and a coveted rooftop bar offering panoramic views of Duval Street. Nestled in the heart of Old Town, this historic venue boasts a lively ambience across its multiple levels.

The rooftop bar stands out as a highlight, providing a perfect vantage point for soaking in the energy of Key West’s bustling street life. Live music performances add to the festive spirit, making it a go-to spot for those seeking a dynamic and entertaining night out. The Bull and Whistle Bar encapsulates the essence of Key West’s lively and diverse nightlife.

16. Shots and Giggles

Shots and Giggles, a vibrant establishment in Key West, carves a niche as a lively shot bar with an infusion of fun and games. Located in the heart of Old Town, this spirited venue offers a dynamic atmosphere perfect for revelry. The highlight lies in its diverse shot menu, catering to a spectrum of tastes and preferences.

Patrons revel in the playful ambience, enhanced by an array of interactive games. The vibrant setting, coupled with the friendly staff, makes Shots and Giggles an ideal spot for those seeking a spirited and laughter-filled night out, capturing the essence of Key West’s lively and entertaining culture.

17. The Waterfront Brewery

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The Waterfront Brewery, nestled in Key West, offers a delightful combination of craft beers, pub-style cuisine, and scenic views. Situated along the waterfront, patrons can enjoy a relaxed ambience with picturesque vistas. The brewery boasts a diverse selection of handcrafted beers, appealing to beer enthusiasts seeking unique flavours.

The menu complements the brews with delectable pub-style food, creating a perfect pairing for a satisfying culinary experience. Whether sipping a signature brew indoors or on the outdoor patio, visitors bask in the laid-back atmosphere. The Waterfront Brewery stands as a go-to destination for those seeking a taste of Key West’s coastal charm and craft beer culture.

18. The Salty Angler Bar

The Salty Angler Bar in Key West beckons patrons with its relaxed charm, offering a casual spot where craft beers, cocktails, and a welcoming atmosphere converge. Nestled in the heart of Old Town, this establishment provides a laid-back setting for locals and visitors alike.

The bar’s appeal lies in its diverse selection of craft beers and well-crafted cocktails, inviting patrons to unwind in a friendly ambience. Whether enjoying a refreshing drink indoors or in the outdoor seating area, The Salty Angler Bar encapsulates the essence of Key West’s easygoing spirit, making it a favoured destination for those seeking a comfortable and enjoyable pub experience.

19. Schooner Wharf Bar

Schooner Wharf Bar, a quintessential Key West gem, invites patrons to its waterfront haven where live music, fresh seafood, and a laid-back atmosphere create an idyllic experience. Nestled in the Historic Seaport, this beloved bar exudes a maritime charm with views of sailboats and the sea.

Live music serenades visitors, enhancing the vibrant ambience. The menu features delectable seafood, capturing the essence of the island’s culinary delights. Whether enjoying a cocktail at the outdoor bar or savouring a meal by the water’s edge, Schooner Wharf Bar embodies the spirit of Key West’s easygoing lifestyle, making it a cherished destination for locals and tourists alike.

20. Half Shell Raw Bar

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Half Shell Raw Bar, nestled on the historic seaport in Key West, beckons patrons with its seafood delights, oysters, and a laid-back setting. A local favourite since 1973, this casual gem captures the essence of the island’s maritime heritage. Overlooking the water, visitors indulge in a fresh and diverse seafood menu, featuring oysters and other culinary treasures from the sea.

The open-air ambience invites guests to savour their meals while enjoying the coastal breeze. With its nautical charm and a menu showcasing the best of Key West’s aquatic bounty, Half Shell Raw Bar stands as a cherished destination for those seeking a relaxed and authentic dining experience.

In the heart of Key West’s vibrant nightlife, a diverse tapestry of bars awaits, each with its unique charm and history. From the iconic Sloppy Joe’s, echoing Hemingway’s spirit, to the laid-back Green Parrot, and the dynamic multi-venue complex of Rick’s Bar, the island offers a playground of possibilities.