Welcome to Key West, where swaying palm trees, crystal-clear waters and the vibrant spirit of the Florida Keys come together in perfect harmony. As much as we adore the picturesque beaches and breathtaking sunsets, there’s one aspect of things to do in Key West that captures the excitement of this island paradise uniquely – its dive bars.
In this blog post, we’re about to embark on a thrilling journey through the hidden gems of Key West’s nightlife scene because, when it comes to bars in Key West, the possibilities are as endless as the ocean views.
But it’s Key West dive bars that truly infuse this place with a special charm. It’s all about embracing a laid-back and friendly atmosphere that captures the true spirit of what a Key West is all about!
Captain Tony’s Saloon
Step into the iconic Captain Tony’s Saloon, the revered birthplace of the Original Sloppy Joe’s and the most time-honored tavern in all of Key West! A beloved haunt for iconic figures like Ernest Hemingway, Truman Capote, Tennessee Williams, Shel Silverstein, and Jimmy Buffet, this is no ordinary bar; it’s a living, breathing relic of days gone by.
Captain Tony, a larger-than-life character himself, was a fisherman, a daring gunrunner, a casino proprietor, and even the Mayor of Key West. He was a figure straight out of a Hemingway novel, full of adventure and intrigue.
As you savor your chilled beverage, consider that you’re partaking in a tradition where legends have been raising their glasses for generations in the vibrant spirit of Key West bars.
Green Parrot
Welcome to the Green Parrot, a place that’s not just a bar – it’s a sanctuary of good times, camaraderie, and everyday adventures.
The Green Parrot goes back to the late 19th century when local musicians gathered in the small back room, filling the air with infectious Latin rhythms and creating impromptu jam sessions that often lasted deep into the night.
Since then, this place has witnessed it all, from raucous poetry slams to tearful divorce celebrations, from solemn memorials to wild hurricane parties, and even the most unforgettable pet birthday bashes. If you can’t get enough of the entertainment scene in Key West, consider adding the Key West Songwriters Festival to your itinerary. Embrace the moment at The Green Parrot and discover what makes this bar such a long-time favorite!
Bobby’s Monkey Bar
Step into Bobby’s Monkey Bar and you’ll be greeted by a wild bunch of Velcro-handed monkeys hanging from chandeliers, perching on every available flat surface and sporting perpetual grins adding a playful and quirky touch to this dimly lit bar.
The real mystery here is, did the monkeys come first, or did the Monkey Bar moniker inspire the jungle-themed decor? That’s a question we can’t quite answer, but one thing’s for sure: the monkey business is in full swing at Bobby’s.
Located just a block away from the bustling Duval Street, this place isn’t your typical bar; it’s an experience. It’s a haven for day drinking, offering a respite from the crowds on Duval Street. Still, it’s at night when this classic dive bar truly comes to life, beckoning with an irresistible “one more drink on the way home” allure. As the night rolls in, a smoky haze blankets the room, and the pool table, an enduring fixture, sees a constant line of players, each stack of quarters representing their turn.
The jukebox, filled with classics, rules during the day but is silenced at night to make way for the real stars: karaoke enthusiasts. Yes, Bobby’s is synonymous with karaoke in Key West. They host it seven nights a week, and the crowd is as diverse as the drinks they serve.
Schooner Wharf Bar
As you wander the Historic Seaport harbor walk in Key West, an oasis of tropical delight suddenly appears on the horizon. The sounds of the finest musicians in the Florida Keys serenade your ears and the aroma of the freshest local seafood ignites your taste buds.
Welcome to The Schooner Wharf Bar, a timeless gem in Key West’s heart that just keeps getting better with age. A beloved institution since 1984, this quirky open-air bar, situated on the former grounds of the Singleton Shrimp factory, lures both tourists and locals with its exceptional blend of special events, delectable cuisine, and sensational live music.
As a live music venue, the Schooner Wharf Bar is second to none. You never know who you might hear, with special guest musicians like Clarence Clemmons of the E Street Band, jazz legend Othello, and blues icons Big Jack Johnson and Johnny Johnson making appearances.
This is a piece of old Key West that will call you back time and time again, a treasure you’ll want to discover anew every visit!
Chart Room Bar
Welcome to Key West’s best-kept secret, the Chart Room Bar!
Nestled within the Pier House Resort & Spa, this legendary watering hole is a piece of old Florida where unforgettable stories are born and where a unique Key West experience awaits.
This isn’t your run-of-the-mill bar; it’s an island institution, a fabled gathering place for iconic figures like Mel Fisher and Jimmy Buffett. Here, numerous Key West stories have woven their tapestry, and cherished memories are crafted.
The moment you step inside, you’ll encounter an unpretentious ambiance, dedicated to the enjoyment of excellent libations and even better camaraderie.
For those seeking a relaxed setting, exceptional drinks, and a diverse blend of patrons, the Chart Room Bar beckons as the ultimate destination.
Plan Your Key West Vacation
Are you ready to discover your new favorite bar in Key West? Browse our entire selection of vacation homes and explore things to do in Key West today!
Where to Stay
Are you dreaming of a Key West vacation that feels like a home away from home? If so, look no further than our luxury Key West vacation rentals. We have something for everyone, including your furry friends, making your escape to this tropical paradise truly unforgettable! Our Key West vacation homes offer the ultimate family-friendly experience, complete with thoughtful guest services and luxurious amenities.
If you’re a water enthusiast, our Key West rentals with docks are a dream come true. Imagine stepping outside your rental and there’s the water, just a few steps away. Whether you’re renting a boat or bringing your own, you’ll have the perfect place to keep it, right at your doorstep ready for you to head out for a day on the beautiful waters. Maybe you love the water but don’t want to spend all day at the beach. In that case, our Key West house rentals with private pools are the perfect choice. You can have the beach nearby and your own private pool to unwind by; the ideal blend of relaxation and adventure!
For the ultimate Key West experience, choose one of our waterfront Key West rentals. These are the most sought-after properties in town and it’s not hard to see why. Whether you’re traveling solo or with your extended family, our waterfront rentals offer the perfect space, all with breathtaking water views.
Since 2015, we, at Key West Vacation Homes have been dedicated to providing exquisite accommodations and top-tier customer service to island visitors. Now it’s your turn to experience the magic of Key West like never before. Check out our Key West vacation rentals today and book your slice of paradise!
