Key West is a magical place where fun, sun, and cocktails collide. Whether you’re a first-timer or a seasoned visitor (with a hangover-proof liver), this little island offers some of the best spots to sip, dance, and enjoy that laid-back vibe you’re craving. From lively tourist favorites to hidden cocktail havens, there’s a bar for everyone in Key West. And while the list of must-visit watering holes is never-ending, I’ve rounded up my top picks.

Oh, and if you manage to visit all of them in one trip, you deserve a medal (or at least a very large glass of water).

Key West Classics to Check Off Your List

1. The Green Parrot

If you love live music and a no-frills atmosphere, The Green Parrot is your jam. This place is practically an institution, and for good reason—it’s one of the oldest bars in Key West. Pop in for soundcheck Sundays, grab some free popcorn, and enjoy the vibe. Just don’t expect fancy frozen cocktails here—blenders are not part of the deal. Instead, sip on a cold beer, tap your toes to killer tunes, and soak up the cool Key West energy.

2. Sloppy Joe’s

Sure, some people call it a tourist trap, but come on—it’s an ICON. With live music all day, solid food options, and famously heavy pours, Sloppy Joe’s is the perfect spot to kickstart your Key West escapade. Plus, it’s family-friendly until 9 PM, so feel free to bring the kiddos (before it transforms into an adults-only ish…party zone).

3. Captain Tony’s Saloon

Captain Tony’s is steeped in history—and a bit of Key West legend. It’s the original Sloppy Joe’s and has ties to, you guessed it, Jimmy Buffett. There’s even a tree growing inside the bar (how’s that for quirky charm?). While you’re there, try the iconic coin toss game outside. Just don’t come crying to me if you miss your shot.

Waterfront Gems for Sunset Sipping

4. Schooner Wharf Bar

If day drinking with a water view is your thing, put Schooner Wharf on your list. Not one but two happy hours a day? Yes, please! Bonus points for heading upstairs to their not-so-secret balcony, where you can enjoy stunning harbor views away from the crowd. Trust me, it’s worth the climb.

5. Sunset Pier

You can’t visit Key West without catching a sunset, and Sunset Pier is the place to do it. With its colorful seating, live music, and picture-perfect vistas, it’s a quintessential Keys experience. Pro tip: Arrive early to snag a prime spot because this place gets packed.

6. Waterfront Brewery

Calling all beer lovers! The Waterfront Brewery brews their own beers and offers stunning views of the water. The indoor/outdoor vibe makes it perfect for hanging out regardless of the weather. Pair a cold one with some of their tasty food options, and you’re good to go.

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For the Party Animals

7. Irish Kevin’s

Rowdy, raucous, and ridiculously fun—Irish Kevin’s is the bar where inhibitions go to die. The live entertainment is interactive (read: you will get pulled into the show), and the vibe is pure Key West chaos. Enter at your own risk… or at least ready for a wild afternoon.

8. The Rick’s Complex

Why settle for one bar when you could have an entire complex? Rick’s is the ultimate party destination on Duval Street with multiple bars, live music, dancing, and a Tree Bar that serves the best Greyhound in town. It’s basically a bar-hopper’s dream come true.

Quirky and Unique Spots

9. The Smallest Bar

This hole-in-the-wall gem is exactly what it sounds like—a teeny, tiny bar with just a few stools. It’s as quirky as it gets, and it’s all about bragging rights. Stop by for a drink and say you’ve been to the smallest bar in Key West. Cheers!

10. Garden of Eden

Okay, this one comes with a disclaimer—it’s clothing optional. Yes, you heard me right. Nestled at the top of a multi-level bar, Garden of Eden is wild, weird, and everything you’d expect from Key West during Fantasy Fest. Go for the views—or the people-watching. Your choice.

Cozy and Relaxed Hangouts

11. Hank’s Hair of the Dog Saloon

A laid-back patio, live music, and tacos from the famed Garbo’s food truck—what more could you ask for? Hank’s is the perfect spot to chill out with a white peach sangria (trust me, it’s divine) and savor the casual island vibes.

12. Rum Bar at the Speakeasy Inn

Rum lovers unite! This intimate little bar boasts over 150 rums and serves up delicious cocktails. Order a rum flight, settle into their cozy seating, and pretend you’re a pirate. No judgment here.

Hidden Gems & Local Favorites

13. Mary Ellen’s

Equal parts fun and funky, Mary Ellen’s is the ultimate low-key spot to grab a grilled cheese, sip frozen Irish coffee, and enjoy the antics of a Chive TV marathon. Don’t miss their “vibrator races” (yes, it’s exactly as strange as it sounds), which benefit local charities.

14. First Flight Island Restaurant & Brewery

Beer enthusiasts will love First Flight, a small brewery located in the historic Pan Am building. History nerds, take note—this was the birthplace of Pan Am Airlines! The charming venue offers a full food menu and craft beers brewed on-site.

15. General Horseplay

For handcrafted cocktails in a cozy, old-timey setting, look no further than General Horseplay. Watch the bartenders work their magic with creative concoctions, and don’t leave before playing one of their happy hour games.

Imbibe and Explore

There you have it—the ultimate list of Key West bars to check out on your next trip! Whether you’re after sunset views, a rowdy party vibe, or a quiet corner to sip your cocktail, there’s something here for everyone.