🍸 Sip Through History: The Ultimate Key West Bar Crawl

Dear Road Trippers,

There’s no better way to experience the soul of Key West than through its iconic bars—and trust us, these walls could talk. Whether you're in it for the cocktails, the characters, or the history, this crawl gives you all three.

Here's your route to island storytelling, one drink at a time.

1. Schooner Wharf Bar

📍 202 William St | Website
🍹 Must-Try: Schooner Lemonade
🪑 History: Once a shrimp shed, this laid-back bar has been serving boaters and locals since the 1980s. It’s now a hub for live music and maritime vibes.

2. Captain Tony’s Saloon

📍 428 Greene St | Website
🥃 Must-Try: Pirate Punch
👻 History: Originally a morgue, this bar became Hemingway’s favorite watering hole. Look up—the bras and business cards tell stories of generations past.

3. The Smallest Bar in Key West

📍 124 Duval St
🍸 Must-Try: Key Lime Pie Shot
📷 History: No frills, no space, no problem. This no-stool nook has become a quirky must-stop photo op in Old Town.

4. The White Tarpon

📍 700 Front St | Website
🍸 Must-Try: Key Lime Pie Martini
🍴 History: A quieter, more refined corner of the bar scene, this lounge is a locals’ pick for seafood and smooth sips.

5. Sloppy Joe’s Bar

📍 201 Duval St | Website
🍹 Must-Try: Sloppy Rita
📚 History: Opened in 1933 and named by Ernest Hemingway himself, this is one of the most famous bars in America.

6. The Green Parrot Bar

📍 601 Whitehead St | Website
🍺 Must-Try: Parrot Pale Ale
🎷 History: Since 1890, this former grocery store-turned-bar has been keeping locals happy. It’s beloved for its funky décor and freewheeling vibe.

7. Sunset Pier at Ocean Key Resort

📍 0 Duval St | Website
🍍 Must-Try: Key Lime Colada
🌅 History: Built as part of a resort revamp in the early 2000s, Sunset Pier is now a prime sunset-watching perch with daily live music.

8. Rick’s Bar Complex

📍 202 Duval St | Website
🍸 Must-Try: Frozen Hurricane
🏝️ History: It’s more than just a bar—it’s an entertainment complex with a wild past and something for everyone, from rockers to karaoke kings.

9. The Tiki House

📍 203 Duval St | Website
🍹 Must-Try: Zombie
🌺 History: A relative newcomer compared to its neighbors, this kitschy-chic tropical lounge brings Polynesian punch and island flair to Duval.

10. Irish Kevin’s

📍 211 Duval St | Website
🍺 Must-Try: Irish Car Bomb
🎤 History: Since 1998, this rowdy Irish-American pub has built a reputation for wild singalongs, live comedy, and total Key West chaos.

11. The Flying Monkeys Saloon

📍 227 Duval St | Website
🍹 Must-Try: Frozen Monkey
🍹 History: Connected to Fogarty’s Restaurant, this bar rose to frozen fame with its wall of slushy machines and buzzing street-front scene.

12. Bull & Whistle Bar / Garden of Eden

📍 224 Duval St | Website
🍺 Must-Try: Bull Rum Punch
🌿 History: Three floors, three vibes—The Bull (open-air live music), The Whistle (sports bar with balcony), and The Garden (clothing-optional rooftop).

13. Tattoos & Scars Saloon

📍 512 Greene St | Facebook
🍺 Must-Try: Local Draft Beer
🎸 History: Tattoos & Scars Saloon - Key West is your hometown bar no matter where you're from!

14. Shots and Giggles

📍 201 Ann St | Website
🥃 Must-Try: Mermaid Water
📺 History: Nestled behind Tattoos & Scars, this hidden gem offers a cozy, divey space for casual drinks and football Sundays.

Which stop are you most excited to hit?
Reply and let us know—or share your favorite bar story for a chance to be featured in a future edition! 🍻

Cheers to the crawl,
Brian

Florida Keys Road Trip Team

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