Best Bars In The Florida Keys: A 2023 Guide To Unwind And Relax

You’ve come to the right place to quickly find the best bars in the Florida Keys! The Florida Keys is a destination that has been close to my heart for the past 20 years. As an avid traveler and a self-proclaimed connoisseur of bars and restaurants, I’ve been visiting the Keys year after year and have had the pleasure of experiencing the hospitality of many of the spots mentioned in this guide. My love for exploring bars in the Keys stems from not just the drinks, but the community and the stories that are shared across the counters.

Now, as you travel down the picturesque Overseas Highway, you will come across a diverse array of bars. From quaint tiki huts that offer panoramic ocean views to historic dive bars brimming with character, the Keys have something for every taste. My multiple trips have allowed me to sip on a variety of refreshing drinks, from classic piña coladas to artisanal craft beers, while taking in the breathtaking surroundings.

What sets the Florida Keys apart is the unique blend of relaxation and liveliness. You can find a laid-back spot to unwind with a drink in hand or a lively venue with live music that compels you to dance under the stars. Having frequented many of these bars over the years, I can vouch for the authenticity and charm that each establishment brings to the table.

So, as you read through this list of the best bars in the Florida Keys, know that these recommendations are backed by years of personal experience and a genuine affection for this beautiful archipelago. Grab your sunglasses, and a sense of adventure, and let’s dive into a carefully-curated selection that’s bound to make your time in the Keys truly unforgettable.

Our Top Picks for Best Bars in the Florida Keys

No Name Pub

Located on Big Pine Key, No Name Pub is a must-visit spot in the Florida Keys. With its dollar bill-covered walls and laid-back atmosphere, you’ll quickly understand its popularity among locals and visitors alike. Known for their delicious pizza and extensive drink menu, make sure you grab a seat at the bar to enjoy a cold beer or one of their famous cocktails.

Green Parrot Bar

Head over to Key West and pay a visit to the iconic Green Parrot Bar. Established in 1890, this no-frills bar is a true gem offering live music, a welcoming atmosphere, and an impressive variety of drinks. Sip on their signature drink, “The Rootbeer Barrel,” while listening to talented local musicians. Don’t forget to snap a picture of their popular neon parrot sign!

Square Grouper Bar and Grill

In Islamorada, the Square Grouper Bar and Grill is a favorite among both locals and tourists. Offering a picturesque waterside setting, this hotspot is perfect for sipping on tropical cocktails while enjoying the ocean breeze. With a menu filled with fresh seafood dishes and an array of craft beers and spirits, you’ll be spoilt for choice.

Alabama Jack’s

As you make your way towards Key Largo, take a pitstop at Alabama Jack’s in Homestead. Technically not in the Florida Keys, but definitely part of the experience. One of Florida Keys’ most popular establishments, this iconic dive bar is famous for its conch fritters and cold beers. Sit on the waterside deck, enjoy the live music, and take in the cool, laid-back vibes.

Caribbean Club

Finally, immerse yourself in a piece of history at the Caribbean Club on Key Largo. Known for being the oldest bar in the Upper Keys, this waterfront spot was also featured in the movie “The Key Largo” with Humphrey Bogart and Lauren Bacall. With daily live entertainment, spectacular sunset views, and an extensive drink menu, it’s the perfect spot to unwind and enjoy the good life that the Florida Keys have to offer.

Scenic Waterfront Bars

Snappers Oceanfront Restaurant and Bar

Located right off the Overseas Highway, Snappers Oceanfront Restaurant and Bar offers stunning views of the Atlantic Ocean. Enjoy your favorite drinks at their fabulous tiki bar while taking in the sights of passing boats. With live music and fresh seafood dishes, it’s a must-visit when you’re in the Florida Keys.

• Waterfront marina
• Unforgettable sunset views
• Live music and entertainment

Sunset Pier

Sunset Pier, situated at the heart of Key West, boasts some of the best views of the marina and sunset in the region. With its prime location, you can enjoy breathtaking vistas of boats and the idyllic island atmosphere. Relax with a signature cocktail at their outdoor tiki bar while watching sunsets over the horizon.

• Picturesque marina setting
• Spectacular sunsets on the Overseas Highway
• Island-inspired tiki bar

Lorelei Cabana Bar

Nestled on the waterfront in Islamorada, Lorelei Cabana Bar offers an immersive experience in the iconic Florida Keys ambiance. Relish the lovely marina filled with boats, and don’t forget to catch one of their highly-acclaimed sunsets. With a sandy floor and a laid-back tiki bar, it’s the perfect spot to unwind during your visit.

• Prime waterfront location
• Mesmerizing sunsets and marina views
• Tropical tiki bar vibes

Historic Bars

Sloppy Joe’s Bar

When you’re in the mood to step back in time, there’s no better place than Sloppy Joe’s Bar. Located at Duval Street, this iconic Key West establishment has been around since 1933 and was a favorite watering hole of the legendary author, Ernest Hemingway. As you sip on your favorite cocktail, feel the presence of Hemingway while enjoying the historic atmosphere. Sloppy Joe’s Bar often holds annual events such as the Hemingway Look-Alike contest, making it a must-visit for fans of the renowned writer.

Bull and Whistle Bar

Another classic spot on your historic bars tour in the Florida Keys would be the Bull and Whistle Bar. Nestled in Key West, this bar boasts a distinguished history as it hails from the early days of the Conch Republic. The Bull and Whistle Bar is split into three unique sections:

• The Bull: A lively ground-floor bar where you can enjoy live music and dancing
• The Whistle Bar: A more relaxed second-floor space, perfect for sipping on a beverage like a classic Rum Runner
• The Garden of Eden: A clothing-optional, open-air rooftop terrace, ideal for adventurous patrons

In addition to the unique settings, you might also appreciate the beautiful architecture of the historic building.

While exploring these historic bars, don’t forget to raise a glass to the famous figures like Humphrey Bogart and Lauren Bacall, who once graced these establishments with their presence. So, grab your friends and make your way through the rich history of the Florida Keys’ bar scene!

Best Bars for Live Music

Irish Kevin’s

You don’t want to miss out on Irish Kevin’s when visiting the Florida Keys! This amazing bar is well-known for its live music and energetic atmosphere. You can expect a good mix of genres as local and regional talent perform at this popular spot. Get ready to dance the night away on their wooden dance floor while sipping your favorite drink. Don’t forget to try their signature Key Lime Pie Punch!

Hog’s Breath Saloon

Another must-see is Hog’s Breath Saloon. With live music every day, it’s no wonder this place is a favorite among locals and tourists alike. Make sure to check out their outdoor stage where they feature the best in local and visiting bands. Hog’s Breath Saloon also offers a fantastic Green Parrot that you should indulge in.

If you are looking for a place with a relaxed atmosphere, take the time to visit Lorelei, located in Islamorada. Although they don’t have a dedicated dance floor, their beach ambiance and live music make it a great choice for a more laid-back evening.

Remember, these are just a few of the many amazing spots to enjoy live music in the Florida Keys. There’s always a good time waiting for you, so start exploring and make some unforgettable memories!

Top Food and Drink Spots

Fisherman’s Cafe

At Fisherman’s Cafe, you can experience a laid-back atmosphere alongside delicious seafood dishes. Enjoy their key lime pie, a must-try dessert when visiting the Florida Keys. Don’t miss out on their drink specials during happy hour, where you can kick back with your favorite cocktails or craft beers.

Indulge in their mouth-watering selection of seafood, including:

• Freshly caught fish dishes
• Savory shrimp platters
• Scrumptious lobster rolls

For those who prefer land-based options, Fisherman’s Cafe also offers a delightful array of non-seafood items such as pizza and juicy burgers. Remember to pair your meal with one of their perfectly crafted beers or cocktails to make your dining experience complete.

The Smallest Bar

Venture into The Smallest Bar, an iconic and intimate spot known for its friendly atmosphere and superb drink selection. Squeeze in and make new friends as you sip on your choice of craft beers or signature cocktails. The Smallest Bar keeps it simple but excels at delivering exceptional service and good times.

During your visit, take advantage of their happy hour deals, ensuring that you don’t break the bank while enjoying yourself. Although The Smallest Bar doesn’t offer a full food menu, it’s the perfect place to relax and quench your thirst after indulging in delectable seafood or pizza from nearby restaurants.

Informal Beachside Bars

Robbie’s Marina

Ahoy, matey! If you’re seeking a laid-back atmosphere at a beachside bar, Robbie’s Marina is just the place for you. Nestled among the mangroves on the picturesque shores of the Florida Keys, this gem of a spot boasts stunning views as you kick back with a refreshing beverage in your hand.

What makes Robbie’s stand out is its diverse array of activities. Aside from sipping on tropical drinks, you’ll find yourself immersed in the local scene, where you can mingle with fellow travelers and residents alike. Take a moment to appreciate the famous mermaid sign adorning the entrance, reflecting the bar’s quirky charm.

Caribbean Club

Welcome to the Caribbean Club! Located in Key Largo, this legendary bar is perfect for those who crave the quintessential Florida Keys experience. With its delightful key lime pie punch, local Florida beer, and a prime spot for witnessing awe-inspiring sunsets, you’ll understand why it’s one of the top hangout spots.

Get your groove on with live music playing on the waterfront, and let the casual atmosphere carry you away. While basking in the warmth of the sun and swaying to the rhythm of the tunes, you’ll find yourself lost in the magic that makes the Caribbean Club an unforgettable beachside escape.

Unique Theme Bars

Florida Keys has some unique and interesting theme bars that you definitely won’t want to miss. Let’s take a moment to explore some of these must-see establishments.

Willy T’s

Another unique spot is found as you head further south on Duval Street to Willy T’s. Known for its eclectic, playful vibe, Willy T’s is decorated with thousands of license plates covering its walls, creating a visually striking experience. In addition to its unusual decor, the bar is also known for its live music and delicious food options. Be sure to stop by and take in this one-of-a-kind atmosphere during your visit to the Florida Keys.

Gearing up for a Bar Crawl

Ready for an epic adventure through the best bars in the Florida Keys? Planning a bar crawl doesn’t have to be a daunting task. With the right tools, you’ll be sipping cocktails and enjoying good company in no time.

First, make sure you’ve got your smartphone handy. Search for a bar crawl app or use popular review sites like Yelp and TripAdvisor to find the most raved-about watering holes. Focus on best Florida Keys bars to get a curated list of top spots to visit during your crawl.

Mix and match your choices based on your preferences – from tiki-style bars to Hemingway-inspired hangouts, the Florida Keys have something for everyone. Consider the ambiance, music, and drink offerings when making your selections.

While you’re browsing reviews, be on the lookout for recent photos and insider tips from other visitors. You can’t go wrong by taking advice from fellow bar crawlers on which spots have the best happy hour deals, unique cocktails, or unforgettable experiences.

Remember to plan your route in advance. It’s important to know the order of your bar stops to avoid backtracking and wasting time. Don’t forget to account for travel time between each location as well. Use Google Maps or another trusted navigation app to estimate distances and travel modes.

Get your friends on board by sharing your selections and the itinerary. Discuss which bars everyone is most excited about visiting and be open to making last-minute adjustments if needed. The key to a successful bar crawl is flexibility and going with the flow.

Before heading out on your adventure, double-check each bar’s hours of operation and any potential cover charges. Knowing what to expect beforehand will help keep your crawl running smoothly.

In the end, the most important part of a bar crawl is having fun with your friends and trying new things along the way. Stick to your plan, but remember to stay safe and responsible. Enjoy the best Florida Keys bars and create lasting memories to cherish forever!

Quick Reference Chart: Best Bars in the Florida Keys

We thought it would be useful for you to see these at quick glance, so you can easily see what part of the Keys these are in and even which mile marker! That way, no matter where you are on your trip you’ll be able to find a great bar to visit easily!

Please note that mile markers (MM) in the Florida Keys are roadside markers that indicate the distance in miles from Key West. MM 0 is in Key West and the numbers increase as you move away from Key West.

Name	Address	Part of the Keys / Mile Marker
No Name Pub	30813 Watson Blvd, Big Pine Key, FL 33043	Lower Keys / MM 30.4
Green Parrot Bar	601 Whitehead St, Key West, FL 33040	Key West / MM 0
Square Grouper Bar and Grill	22658 Overseas Hwy, Summerland Key, FL 33042	Lower Keys / MM 22.5
Alabama Jack’s	58000 Card Sound Rd, Homestead, FL 33030	Mainland, near Upper Keys
Caribbean Club	104080 Overseas Hwy, Key Largo, FL 33037	Upper Keys / MM 104
Snappers Oceanfront Restaurant and Bar	139 Seaside Ave, Key Largo, FL 33037	Upper Keys / MM 94.5
Sunset Pier	0 Duval St, Key West, FL 33040	Key West / MM 0
Lorelei Cabana Bar	96 Madeira Rd, Islamorada, FL 33036	Upper Keys / MM 82
Sloppy Joe’s Bar	201 Duval St, Key West, FL 33040	Key West / MM 0
Bull and Whistle Bar	224 Duval St, Key West, FL 33040	Key West / MM 0
Irish Kevin’s	211 Duval St, Key West, FL 33040	Key West / MM 0
Hog’s Breath Saloon	400 Front St, Key West, FL 33040	Key West / MM 0
Fisherman’s Cafe	205 Elizabeth St Unit D, Key West, FL 33040	Key West / MM 0
The Smallest Bar	124 Duval St, Key West, FL 33040	Key West / MM 0
Robbie’s Marina	77522 Overseas Hwy, Islamorada, FL 33036	Upper Keys / MM 77.5
Willy T’s	525 United St, Key West, FL 33040	Key West / MM 0

Nightlife Beyond Bars

Schooner Wharf Bar

When you’re visiting the Florida Keys and craving a bit of nightlife beyond the typical bars, make sure to check out Schooner Wharf Bar. This laid-back, open-air waterfront spot offers more than just a place to grab a drink – it’s an experience!

The atmosphere at Schooner Wharf Bar is always lively, as they feature live music every day for your entertainment. You can enjoy the tunes of local and visiting musicians while sipping on refreshing cocktails and soaking in the unique ambience of the surrounding yachts and marina.

During the day, you can drop by for breakfast, lunch, or dinner, as they offer a mouthwatering menu filled with a variety of options such as seafood dishes, sandwiches, and salads. If you happen to be a sports fan, don’t worry – Schooner Wharf Bar doubles as a sports bar, so you’ll be able to catch a game or two while you’re there.

Ribicoff’s Restaurant

For a more low-key vibe with a focus on the dining experience, you’ll want to make reservations at Ribicoff’s Restaurant. This hidden gem in the Florida Keys offers a relaxing and intimate atmosphere away from the hustle and bustle of bars and clubs.

At Ribicoff’s, you can select from a menu that features breakfast, lunch, and dinner options, using the freshest ingredients. You might want to indulge in their extensive wine list, showcased by excellent service and attentive staff.

While Ribicoff’s Restaurant doesn’t have the same nightlife scene as other bars, it does offer occasional live music on select evenings. This creates a cozy environment where you can enjoy a romantic dinner or a catching-up session with friends, all while taking in the melodious tunes of talented musicians.

In summary, if you’re seeking some nightlife beyond bars in the Florida Keys, your best bet is to explore the diverse atmospheres of Schooner Wharf Bar and Ribicoff’s Restaurant. Between live music, picturesque scenery, and delicious food, these places are sure to leave you with lasting memories of your visit to this one-of-a-kind destination.

Recap: Best Bars in the Florida Keys

As the sun sets on our journey through the captivating bars of the Florida Keys, I hope this guide has been your trusty first mate, steering you to some truly remarkable havens. Having frequented these isles for two decades, I can say with conviction that the essence of the Keys is captured not just in the azure waters but in the laughter, stories, and clinking glasses at these bars.

Whether you sought refuge in a serene tiki hut, or let the rhythm guide your feet on a vibrant dance floor, may your sails always be full of the memories made here. The Florida Keys, with their enchanting blend of island charm and spirited camaraderie, will always beckon for another round. Until the next tide brings us back, cheers to the memories and the tales yet unwritten in the heart of the Keys. 🍹

Frequently Asked Questions

What are the top waterfront bars in the Keys?

When you’re in the Keys, you’ll want to enjoy the breathtaking views while sipping on a refreshing drink. Some of the best waterfront bars include Alabama Jacks, which is technically in Homestead but offers an authentic Florida Keys vibe, and the Sugarloaf Lodge Tiki Bar, known for its beautiful setting.

Which bars in Islamorada should I visit?

Islamorada is home to several bars worth checking out. Be sure to visit the Islamorada Wine Co., which offers a unique experience compared to the traditional rum and margarita-focused bars. You’ll find an extensive wine selection alongside a laid-back atmosphere.

What are the best tiki bars in Marathon?

As you make your way through Marathon, don’t miss the chance to relax at a tiki bar. Though specific bars may not be mentioned in the search results, keep an eye out for establishments advertising a tiki bar atmosphere and tropical cocktails to enjoy under the Florida sun.

Which Key Largo bars are worth checking out?

Key Largo is home to various great bars. Although exact names were not mentioned in the search results, be sure to explore local bars and pubs, especially near the marina or waterfront locations, where you can take in stunning views and mingle with other travelers and locals.

Where can I find great nightlife in the Keys?

As you journey through the Keys, you’ll find vibrant nightlife scattered throughout the islands. Look for popular bars with live music and entertainment, such as Hank’s Hair Of The Dog Saloon. You can also check local listings or ask residents for their recommendations.

What’s the top party spot in Key West?

Key West is known for its lively atmosphere, so it’s no wonder there are many great party spots. Though a specific location is not provided, be sure to hit up the bars along Duval Street, as this area is famous for its bustling nightlife. You’re sure to find the perfect spot to let loose and have a great time.