Key West is more than just a tropical paradise. It’s a place where history comes alive, especially in its iconic bars. These watering holes are not just spots to grab a drink—they’re living museums filled with tales of pirates, literary legends, and maritime adventures.
Take Captain Tony’s, for example. This legendary bar has been a cornerstone of the island for years. It’s where Ernest Hemingway once raised a glass and where locals and visitors alike gather to share stories. Then there’s Sloppy Joe’s, a vibrant hub that keeps the spirit of the Florida Keys alive with its lively atmosphere and rich history.
Schooner Wharf Bar adds its own charm, housed in a repurposed shrimp house from the 1990s. It’s a testament to the island’s ability to blend the old with the new. And don’t forget The Smallest Bar, a quirky 72-square-foot spot on Duval Street that’s perfect for a quick photo and a Key Lime Pie Shot.
These bars are more than just places to drink. They’re community hubs where Jimmy Buffett tunes meet treasure-hunting legends like Mel Fisher. Each one offers a unique glimpse into the heart and soul of Key West.
Key Takeaways
- Key West bars are living museums of island history.
- Captain Tony’s and Sloppy Joe’s are iconic pillars of the island’s culture.
- Schooner Wharf Bar showcases adaptive reuse in a historic setting.
- The Smallest Bar is a quirky, must-visit spot on Duval Street.
- These bars are community hubs, blending music, history, and tradition.
Key West’s Bar Scene: Where History Meets the Tropics
The island’s bars are more than just places to grab a drink—they’re cultural landmarks. These establishments are woven into the fabric of Key West, offering a glimpse into its colorful past. From pirate tales to literary legends, every bar has a story to tell.
Why Key West’s Bars Are More Than Just Drinking Spots
Bars like Captain Tony’s and Sloppy Joe’s are pillars of the island’s identity. Captain Tony’s, originally a morgue in 1851, is now a lively hub where patrons leave bras and business cards on the ceiling. This tradition dates back to the 1930s, creating a timeline of stories etched into its walls.
Sloppy Joe’s, opened in 1933, is another iconic spot. Named by Ernest Hemingway, it became his workspace where he wrote parts of To Have and Have Not. These bars are not just about the drink—they’re about the people and the history they preserve.
The Role of Bars in Key West’s Colorful Past
Schooner Wharf Bar is a prime example of the island’s maritime roots. Once a bustling hub during the 1800s shrimping boom, its docks were so packed you could cross the harbor without touching water. Today, it hosts over 30 annual events, including the Minimal Regatta and Pirate Wench ceremony.
Its dual happy hours, from 7am to noon and 5pm to 7pm, foster all-day socializing. Meanwhile, The Green Parrot, which started as a grocery store in 1890, survived Prohibition as a speakeasy. These bars are living testaments to the island’s resilience and creativity.
| Event | Description |
|---|---|
| Minimal Regatta | A quirky boat race using homemade vessels. |
| Pirate Wench Ceremony | A lively celebration of pirate lore and costumes. |
| Dual Happy Hours | Morning and evening happy hours for all-day fun. |
Key West’s bars are more than just businesses—they’re community hubs where music, history, and tradition come together. Whether you’re sipping a drink or listening to live tunes, you’re part of a story that’s been unfolding for generations.
Legendary Bars That Shaped Key West’s Culture
The walls of Key West’s iconic bars whisper tales of pirates and poets. These spots blend history with tropical charm, serving up cocktails and stories in equal measure.
Captain Tony’s Saloon: From Morgue to Hemingway’s Hangout
At 428 Greene Street, Captain Tony’s began as an 1851 icehouse and morgue. By the 1930s, it became Ernest Hemingway’s poker spot. This saloon wears its past proudly—patrons leave bras and IDs on the ceiling, a tradition since WWII.
Try the Pirate Punch, a rum-heavy drink that fuels late-night storytelling. The live music here keeps the spirit of the florida keys alive.
Sloppy Joe’s: The Bar Ernest Hemingway Named Himself
Hemingway insisted owner Joe Russell rename this spot from “The Blind Pig.” Inspired by a Havana speakeasy, Sloppy Joe’s became his writing den. Sip a Sloppy Rita, a tequila twist on the classic, under photos of the author.
Schooner Wharf Bar: A Nautical Dive with Maritime Roots
This bar is a tribute to the sea. Salvaged ship wheels and Mel Fisher’s treasure maps line the walls. The pet-friendly sand floor and Schooner Lemonade make it a local favorite.
Fun fact: Robert Morton’s spy novels mention it as a CIA debriefing spot.
| Event | Highlights |
|---|---|
| Minimal Regatta | Homemade boats race for quirky glory. |
| Pirate Wench Ceremony | Costumed revelry celebrating pirate lore. |
| Dual Happy Hours | 7am-noon & 5pm-7pm for all-day fun. |
Hidden Gems and Quirky Watering Holes
Beyond the well-known spots, Key West hides quirky watering holes that tell their own unique tales. These places may not have the fame of the island’s iconic bars, but they offer charm, character, and a chance to experience something truly special.
The Smallest Bar in Key West: No Space, No Problem
At 124 Duval Street, you’ll find The Smallest Bar, a 72-square-foot spot that’s big on personality. With no stools and just enough room for a few people, this tiny bar is a must-visit for its novelty and Instagram-worthy appeal.
Their menu features Key Lime Pie Shots, served in souvenir glasses that make for perfect keepsakes. The walls are plastered with vintage license plates, adding to the quirky vibe. Despite its size, this place has garnered over 15,000 geotagged posts, proving that good things really do come in small packages.
The Green Parrot: A Funky Time Capsule Since 1890
Just a short walk from Hemingway House, The Green Parrot has been a staple of the island for over 130 years. What started as a grocery store in 1890 survived Prohibition as a speakeasy and later transformed into a jukebox-packed blues bar.
Today, it’s known for its Parrot Pale Ale and late-night punk shows. The original 1890s tin ceiling and laid-back atmosphere make it a favorite among locals and visitors alike. It’s a place where music, history, and good drinks come together in the best way possible.
- The Smallest Bar: Compact, quirky, and perfect for a quick drink and photo op.
- The Green Parrot: A historic spot with a funky vibe and a rich story to tell.
- Both venues offer a unique experience that goes beyond the typical bar scene.
Conclusion: Raising a Glass to Key West’s Legacy
Step into a world where every drink comes with a tale. Key West’s historic bars are more than just places to unwind—they’re gateways to the island’s vibrant past. Sip Hemingway’s Sloppy Rita at Sloppy Joe’s or savor the Pirate Punch at Captain Tony’s. Each cocktail is a nod to the stories that shaped this place.
Plan your visit around Schooner Wharf’s lively events, like April’s Wreckers Race or December’s Lighted Boat Parade. With 70% of the island’s bars within walking distance on Duval and Greene Streets, exploring is a breeze. Don’t forget to share your own experiences using #KeyWestBarHistory.
As Schooner Wharf says, “No trip is complete without meeting our dogs, musicians, and sunset regulars.” Raise a glass and toast to the history, music, and spirit of this unforgettable island.