Key West is famous for its vibrant nightlife, with iconic spots like Sloppy Joe’s and The Green Parrot drawing crowds night after night. However, for those with a taste for adventure and a penchant for discovering the local flavor, the island is teeming with lesser-known Key West bars that offer unique experiences and a more intimate ambiance. Let’s dive into five of these hidden treasures, starting with the historic Chart Room, and journey through some of the most intriguing bars that you probably haven’t experienced yet.
1. The Chart Room: A Storied Legacy
Located within the Pier House Resort, the Chart Room is a true slice of local history. Established in the 1960s, this bar has been a favorite haunt for both locals and travelers seeking a snug and nostalgic atmosphere. The Chart Room is more than just a bar; it’s a time capsule filled with maritime memorabilia, maps, and an assortment of quirky knick-knacks that tell tales of the past.
What Makes It Special:
- Rich History: Frequented by legends like Jimmy Buffett and Mel Fisher, the Chart Room offers you a chance to sip your drink where history was made.
- Free Popcorn and Hot Dogs: Yes, you read that right! Enjoy complimentary snacks as you soak up the ambiance.
- Intimate Setting: With just a handful of seats, the Chart Room ensures a cozy environment perfect for striking up conversations with fellow patrons or the friendly bartenders.
Must-Try: The Rum Runner
Go for their Rum Runner, a tropical blend of rum, banana liqueur, blackberry brandy, orange juice, and grenadine. It’s a perfect drink to sip while soaking in the bar’s rich history.
Open everyday from 5pm to midnight.
1 Duval Street, Key West, FL 33040
2. Dive Bar Shirt Club Bar: A Dive into the Unique
Tucked away from the bustling streets, the Dive Bar Shirt Club Bar is a haven for those who appreciate the charm of dive bars. As the name suggests, this bar is part of a unique club that celebrates dive bars around the country by featuring a different one on their exclusive T-shirts each month. Tooted as part shirt club, part museum, and part dive bar, Dive Bar Shirt Club is a fun off-Duval addition to the Key West community.
What Makes It Special:
- Exclusive T-Shirts: Membership to the Dive Bar Shirt Club gets you a cool, new T-shirt every month, showcasing various dive bars across the nation.
- Eclectic Decor: The walls are adorned with dive bar memorabilia, creating a warm and welcoming atmosphere.
- Simple Drinks: Enjoy a range of beer and wine along with some signature bar food such as tacos and burritos.
Must-Try: Anything That Makes You Happy
It’s a dive bar, after all. Just grab a beer or wine and relax.
Open every day from 11am-11pm.
320 Grinnell Street, Key West, FL 33040
3. Berlin’s: Elegance in Every Sip
For those who prefer a touch of sophistication, Berlins’s, located at the top of the esteemed A&B Lobster House,l is the place to be. This stylish speakeasy offers a refined, upscale experience with a menu that boasts an impressive array of martinis and other crafted cocktails.
What Makes It Special:
- Beautiful Views: Situated on the top floor, Berlin’s offers breathtaking panoramic views of Key West harbor, perfect for a romantic evening or a chic night out. There is even a cigar terrace if you feel the need to relax soak in the cooler night air.
- Extensive Martini Menu: From classic martinis to innovative creations, there’s something to satisfy every palate.
- Serene Ambience: Enjoy the soothing sounds of live jazz or acoustic sets as you sip on your expertly crafted cocktail all while comfortable in one of their leather club chairs.
Must-Try: The Manhattan
Berlin’s take on the popular Manhattan drink includes the delightful Four Roses Small Batch Bourbon. As one of their bartenders most recommended drinks, it is a must-try.
Open Daily, 5pm – 11pm
700 Front Street, Key West, FL 33040
4. Little Room Jazz Club: Where Music and Ambiance Meet
Music enthusiasts will find their haven at the Little Room Jazz Club. Nestled on the quiet end of Duval Street, this bar offers an intimate setting where the focus is on high-quality jazz performances. It’s a place where you can lose yourself in the music and enjoy a sophisticated evening with some of the most carefully crafted cocktails on the island.
What Makes It Special:
- Live Music Performances: Experience exceptional live music (not just jazz) in a cozy venue that brings you up close and personal with the musicians.
- Upscale Atmosphere: The elegant decor and intimate seating arrangements make it an ideal spot for a special night out.
- Craft Cocktails: The cocktail menu is carefully curated to complement the musical experience, featuring both classic and innovative drinks.
Must-Try: The Ella Fitzergerald
Order the Ella Fitzgerald to try a beautiful mix of Key West and old-time elegance. With strawberry gin, prosecco, and simple syrup, it perfectly complements the sultry sounds of jazz filling the room.
Open Tuesday – Saturday 5pm-midnight
821 Duval Street, Key West, FL 33040
5. The Roost: Cheers to the Best Kept Secret
Last but certainly not least, The Roost is a hidden gem that offers a laid-back, friendly vibe. Located just off the beaten path, this bar is a favorite among locals who appreciate its unpretentious atmosphere and welcoming staff. The Roost also offers a daily happy hour from 12-6 as well as daily specials, such as Tequila Tuesdays and Old-Fashion Wednesdays.
What Makes It Special:
- Craft Beer Selection: The Roost boasts an extensive selection of local beers, perfect for beer enthusiasts looking to try something new.
- Impressive & Unique Cocktail List: This is not your run-of-the-mill Key West bar. Give your taste buds something jolting and new with their delicious craft cocktails.
- Cozy Ambiance: The warm, inviting decor makes it a great spot to unwind and relax with friends after a long day of exploring.
- Knowledgeable Staff: The bartenders at The Roost are passionate about their craft and always willing to share recommendations or whip up a custom creation just for you.
Must-Try: Blowing Smoke Up Your Glass
With Papa’s Pilar 24 year dark rum, pineapple, house-made smoked basil syrup, lime and bitters, this drink will have you wondering how you ever vacationed before. Tropical yet refined, this drink will knock your socks off (if you were ever wearing any to begin with).
Open daily noon-11pm
508 Fleming Street, Key West, FL 33040
Wrapping Up Your Key West Adventure
While Key West is known for its bustling mainstays, it’s the hidden treasures that often create the most memorable experiences. Whether you’re a history buff, a lover of live music, or simply someone looking to enjoy a well-crafted drink in a unique setting, these five lesser-known bars offer something for everyone.
What other suggestions do you have for our readers? Leave your experiences below! We can’t wait to hear all about your fabulous Key West finds.
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