Key West Bar Crawl Guide 2024

Key West Bar Crawl Guide 2024

Welcome, thirsty adventurers, to the vibrant and eclectic island paradise of Key West, Florida! Nestled at the southernmost tip of the United States, this small yet lively city is an oasis of sun, sand, and, most importantly, sensational watering holes. Get ready to dive into a world of cocktails, local brews, and tropical vibes on this journey through the ultimate Key West bar crawl extravaganza. So, slip on your flip-flops, grab your sunglasses, and get ready to toast your way through the best bars this tropical haven has to offer.

First Stop: The Green Parrot Bar

601 Whitehead St, Key West, FL 33040

The first port of call is none other than the legendary Green Parrot Bar. Tucked away on Whitehead Street, this dive bar is a truly iconic institution on the Key West bar scene. Expect lively tunes, a funky ambiance, and a crowd brimming with character and fun. It's the kind of place where you'll find yourself dancing with strangers, belting out tunes with the live band, and enjoying a chilled beer or their famous mojitos.

Next Up: Sloppy Joe's Bar

201 Duval St, Key West, FL 33040

Time to amble down Duval Street to visit the ever-lively Sloppy Joe's Bar. This iconic spot has a history as colorful as its décor. A favorite haunt of Ernest Hemingway, it’s got that old-school charm mixed with a dash of Key West's spirited energy. From live music to their legendary rumrunners, you're guaranteed a great time. Try the spicy watermelon mojito, Key West citrus vodka lemonade, or frozen bacardi light rum strawberry daiquiri. Don’t leave without snagging a souvenir T-shirt – it’s a rite of passage for any Key West bar crawler.

Hog’s Breath Saloon: Hog Heaven Awaits

400 Front St, Key West, FL 33040

Now, shift gears and mosey over to Hog's Breath Saloon. The atmosphere here is as laid-back as it gets, making it the perfect place to kick back, grab a refreshing cocktail, and enjoy the live music. Try a signature concoction like the Goombay Smash or Hogarita while soaking in the vibrant vibes and ocean breeze.

The Smokin’ Tuna Saloon: A Melodic Pause

4 Charles Street, Duval St 200 Block, Key West, FL 33040

Escape the hustle and bustle for a moment and swing by the Smokin’ Tuna Saloon. With its intimate setting and talented live performers, this spot offers a soulful break in your bar crawl adventure. Savor a craft beer or one of their specialty cocktails while tapping your feet to the rhythm of the music.

Sunset Pier at Ocean Key Resort & Spa: Sundown Cheers

0 Duval St, Key West, FL 33040

As the sun begins its descent, head to Sunset Pier for a magical experience. Nestled at the gorgeous Ocean Key Resort & Spa, this is the ideal spot to witness the breathtaking Key West sunset. Sip on a tropical cocktail while the sky transforms into a canvas of vivid colors – it's a moment you won’t soon forget.

The Waterfront Brewery: Elevated Revelry

201 William St, Key West, FL 33040

After soaking in the glorious sunset, elevate your night at The Waterfront Brewery at the Historic Key West Bight marina. Enjoy stunning views of the waterfront while indulging in their craft beer selection or a creative cocktail. With a relaxed atmosphere and great company, this is the perfect setting for a chill yet lively evening.

Take a Guided Bar Crawl Tour

Are you looking to elevate your Key West bar-crawling experience even further? Fear not, as several local companies specialize in organizing fun-filled bar crawls, ensuring you make the most of your tropical tour. These companies expertly curate and guide participants through the city’s best watering holes, providing a hassle-free and memorable adventure.

Tour operator Key West Pub Crawls is renowned for its well-organized and entertaining crawls. Offering both daytime and evening tour options, their knowledgeable guides lead participants through a handpicked selection of Key West’s best bars. With perks such as skip-the-line access, exclusive drink specials, and a vibrant atmosphere, these organized crawls add an extra layer of excitement to your bar-hopping escapade. Their local expertise and insider tips guarantee that you uncover hidden gems and local favorites you might have missed otherwise.

Congratulations, bar crawl champs! You've conquered Key West, drink by drink. From the lively beats of the Green Parrot Bar to the laid-back charm of Hog's Breath Saloon and the mesmerizing sunset at Sunset Pier, you've experienced the heart and soul of Key West’s thriving bar scene. As the night winds down, you’ll carry with you memories of laughter, great drinks, and the infectious energy of this remarkable island city.

Ready to start your real estate journey in Key West?

If you’re enticed by everything that life in Key West has to offer — from the stunning views to the amazing bars — team up with only the best to begin your home search. Partner with Ocean Sotheby’s International Realty to explore the Key West real estate landscape. With trusted broker Russell Post at the helm, this top-tier team is ready to guide you to your new piece of paradise. Connect with the team today to begin.

Connect With Us

Start Your Home Search

Follow Us on Instagram