Planning a trip to Key West? Sure, you know about the sunsets, the palm trees, and maybe even the famous Key Lime pie—but did you know this island is also home to some of the quirkiest, coolest bars you’ll ever stumble into? And what better way to explore them than with a bar crawl? Forget the overly hyped tourist spots for a night and join me on a Key West bar adventure that’s a little off the beaten path.
This guide will take you to six unique bars, each with its own personality and vibe. From craft cocktail hideaways to tiki havens, we’ve got you covered. Plus, I’ll throw in tips on how to survive and thrive through your night of libations. Comfy shoes? Check. Hydration? Double check. A willingness to explore? That’s all you’ll need.
Why a Bar Crawl in Key West?
Key West is small enough to explore on foot, making it perfect for a leisurely bar crawl. It’s packed with a diverse mix of watering holes that’ll take you from tiki vibes and speakeasy settings to live music and local hangouts. Plus, this is Key West. The laid-back island vibe means you can sip, stroll, and repeat without any judgment.
Are you ready? Here we go!
Stop 1: The Roost
Location: Fleming Street
The Roost is the ideal place to kickstart your night. It’s intimate, stylish, and oozes cool with its craft cocktails and cozy vibe. They have a liquor store on-site (yes, you can grab a bottle for later), and from time to time, they serve small bites. Start here, sip something fancy, and plot out the rest of your bar crawl. Trust me, one Old Fashioned here sets the tone for the night in the best possible way.
Stop 2: Rum Bar at the Speakeasy Inn
Location: Duval Street
Okay, next, we’re heading to the Rum Bar. Tucked inside the Speakeasy Inn, this spot is all about the rum (as the name suggests). Order a rum flight or a classic rum-based cocktail like a Rum Runner. Don’t forget to say hi to the resident cat, who, frankly, has more Key West street cred than the tourists outside. The vibe here is small, cozy, and undeniably charming, which makes it the perfect continuation of your crawl.
Pro Tip: They don’t serve food here.
Stop 3: The Tiki House
Location: Green Street
Welcome to tiki paradise. The Tiki House is where you’ll feel like you’ve stepped back in time to the heyday of Polynesian pop culture. With retro designs and authentic tiki cocktails, this place brings the fun with drinks that might even be set on fire. If you’re into bold flavors presented with flair, you’ve found your spot. Bonus points if you manage to snag one of their signature tiki mugs.
Stop 4: Green Parrot Bar
Location: Whitehead Street
No frills. No pretensions. The Green Parrot Bar is a Key West classic that keeps things straightforward in all the right ways. The drink menu is basic (you won’t find any flaming cocktails here), but the energy is electric, thanks to their incredible live music. Be sure to check the band’s schedule in advance so you don’t miss out on the jazzy, funky, bluesy juju this bar is famous for. Oh, and yes, there’s free popcorn. Local hack? Load up on it to keep the party going.
Stop 5: General Horseplay
Location: Caroline Street
Prepare for a bit of whimsy with some seriously good drinks. General Horseplay is where creativity meets community, with cocktails that feel like mini works of art. Their old-fashioned is legendary, but honestly, you can’t go wrong with anything on the menu. There’s an outdoor area with games, and the vibe is buzzing yet welcoming. End your night here, or…
Bonus Stop: The Chart Room
Location: Ocean Key Resort & Spa
If you’re still in the mood for one last round, the Chart Room is an iconic spot for a true Key West nightcap. With its chill ambiance and historic reputation (seriously, this place has a lot of stories to tell), it’s worth the detour. This hidden gem opens later in the day, making it the perfect final stop to reflect on your bar crawl adventures.
Tips for a Successful and Fun Bar Crawl
- Hydrate! Alternate your drinks with water. It’ll save you from regretting everything the next day.
- Comfy shoes are your BFF. You’ll be walking over a mile throughout the night, and flip-flops probably won’t cut it.
- Pace yourself. There’s no rule saying you have to drink at every stop. Feel free to order water or take it easy.
- Check schedules in advance. Want to catch live music? Make sure you know which bands are playing and when.
- Flexibility is key. See a random bar that tickles your fancy? Pop in! The worst that can happen is it’s not your vibe, and you simply move on.
Grab our Free Happy Hour List – here
Make It Your Own Adventure
Key West is full of surprises. Use this guide as a starting point but don’t be afraid to veer off course. Some of my best recommendations came from wandering into a bar I’d never heard of and striking up conversations with locals.
Your Key West bar crawl promises unique cocktails, memorable moments, and plenty of stories to tell. Whether you stick to the stops on this list or build your own route along the way, you’re in for one dynamic night.
Cheers to good drinks, even better company, and unforgettable Key West nights!
