Exploring Key West's Historic Bars

Welcome to the vibrant and captivating world of historic bars in Key West! Nestled in the southernmost point of the United States, Key West is not only known for its stunning beaches and laid-back atmosphere, but also for its rich history and vibrant bar scene. In this article, we will take you on a journey through time as we explore some of the most iconic and charming historic bars that have become an integral part of Key West’s cultural fabric.

As you stroll through the narrow streets of Old Town, you’ll find yourself transported to a bygone era, where Hemingway sipped his favorite co*cktails and famous writers sought inspiration. One such legendary establishment is Sloppy Joe’s Bar, which has been a cornerstone of Key West’s social scene since 1933. Step inside, and you’ll be greeted by a lively atmosphere, live music, and a wide array of libations. From classic mojitos to their signature rum runners, Sloppy Joe’s offers a taste of history with every sip.

Another must-visit historic bar is the Green Parrot, a beloved local haunt that dates back to the 19th century. Known as “the last bar on earth,” the Green Parrot exudes a timeless charm with its weathered wooden exterior and eclectic decor. Inside, you’ll find a diverse crowd of locals and visitors alike, all drawn to the bar’s laid-back ambiance and impressive selection of craft beers. Whether you prefer a hoppy IPA or a smooth stout, the Green Parrot has something to satisfy every beer aficionado’s palate.

For those seeking a touch of elegance and sophistication, a visit to the historic Chart Room Bar at the Pier House Resort is a must. With its panoramic views of the Gulf of Mexico, this iconic bar has served as a gathering place for locals and celebrities alike. Sip on a classic martini or indulge in their extensive wine list as you soak in the breathtaking sunset views. The Chart Room Bar is a testament to Key West’s allure, offering a perfect blend of luxury and island charm.

As you explore the historic bars of Key West, you’ll not only be immersed in the city’s rich history but also experience the unique ambiance and character that each establishment has to offer. From lively music to friendly locals, every bar has its own story to tell. So grab a seat at the bar, raise a glass, and let the spirit of Key West’s historic bars transport you to a bygone era of charm and nostalgia. Cheers to a memorable journey through the historic bars of Key West!

Schooner Wharf Bar

Schooner Wharf Bar is a historic and iconic establishment located in Key West, Florida. This bar is known for its laid-back atmosphere, live music, and waterfront location. It has been serving locals and tourists alike since 1984, making it one of the oldest bars in Key West.

The moment you step foot into Schooner Wharf Bar, you are transported back in time. The bar is housed in a charming wooden building with a rustic, maritime-inspired interior. The walls are adorned with nautical memorabilia, vintage photographs, and colorful artwork, creating a cozy and nostalgic ambiance.

One of the highlights of Schooner Wharf Bar is its outdoor seating area, which offers stunning views of the Key West Bight. You can enjoy your drinks while watching boats sail by and listening to the sound of live music filling the air. The bar also has a stage where local bands and musicians perform, adding to the vibrant atmosphere.

Now, let’s talk about the drinks. Schooner Wharf Bar offers an extensive selection of beers, wines, and spirits to suit every taste. Whether you’re a fan of craft beers, classic co*cktails, or fine wines, you’ll find something that tickles your taste buds. The bartenders are knowledgeable and friendly, always ready to recommend a drink or share a story.

When it comes to food, Schooner Wharf Bar doesn’t disappoint. They serve up delicious seafood dishes, such as conch fritters, peel-and-eat shrimp, and fresh fish tacos. The menu also includes mouthwatering burgers, sandwiches, and salads. The portions are generous, and the flavors are on point.

Schooner Wharf Bar is not just a place to grab a drink and a bite to eat; it’s a place to experience the true essence of Key West. The bar hosts various events throughout the year, including fishing tournaments, live music festivals, and charity fundraisers. It’s a hub of activity and a gathering spot for locals and visitors alike.

Schooner Wharf Bar is a must-visit if you’re in Key West. With its historic charm, waterfront location, live music, and delicious food and drinks, it offers a truly unique and memorable bar experience. So, grab a seat, relax, and soak in the laid-back vibes of this iconic Key West establishment.

Sloppy Joe’s

Welcome to Key West, the vibrant and lively island city known for its rich history and vibrant nightlife. If you’re looking for a taste of the past while enjoying a refreshing drink, Sloppy Joe’s is the perfect place for you. Let’s take a closer look at what makes this historic bar a must-visit destination.

Located on the iconic Duval Street, Sloppy Joe’s has been a staple of the Key West bar scene since it first opened its doors in 1933. This legendary watering hole was originally named “The Blind Pig” and operated as an underground speakeasy during the Prohibition era. Its founder, Joe Russell, later moved the bar to its current location and renamed it Sloppy Joe’s.

Walking into Sloppy Joe’s is like stepping back in time. The interior exudes a rustic charm with its vintage décor, wooden furnishings, and walls adorned with old photographs and memorabilia. The atmosphere is lively and energetic, with live music filling the air every night. Whether you’re a history buff or simply looking for a good time, Sloppy Joe’s offers a unique experience that is sure to leave a lasting impression.

Now, let’s talk about the drinks. Sloppy Joe’s boasts an extensive drink menu that caters to all tastes. From classic co*cktails to local favorites, there’s something for everyone. Here are some highlights:

Smallest Bar

Located in the heart of Key West, Smallest Bar is a historic gem that should not be missed. As the name suggests, it is known for being one of the smallest bars in the area, but what it lacks in size, it makes up for in character and charm.

Here are some key points to know about Smallest Bar:

Atmosphere: Stepping into Smallest Bar feels like taking a step back in time. With its vintage decor, dim lighting, and cozy seating, it exudes a laid-back and intimate vibe. The bar is often filled with locals and tourists alike, creating a friendly and welcoming atmosphere.
History: Smallest Bar has a rich history that dates back to the early 1900s. It has been serving drinks to patrons for over a century, making it a true institution in Key West. The bar has managed to preserve its old-world charm, making it a must-visit for history enthusiasts.
Drink Selection: Despite its small size, Smallest Bar offers an impressive selection of drinks. From craft beers to classic co*cktails, there is something to satisfy every palate. The bartenders are knowledgeable and skilled, ensuring that each drink is expertly crafted.
Live Music: One of the highlights of Smallest Bar is its live music performances. Talented local musicians take to the stage, providing a lively and entertaining backdrop to your evening. Whether you’re a music lover or simply looking for a fun night out, the live music at Smallest Bar is sure to please.
Outdoor Seating: If you prefer to enjoy your drinks al fresco, Smallest Bar has a quaint outdoor seating area. Situated on the sidewalk, it offers a prime spot for people-watching and soaking up the vibrant atmosphere of Key West.
Happy Hour: Like many bars in Key West, Smallest Bar offers a happy hour that is not to be missed. With discounted drinks and specials on select menu items, it’s a great way to enjoy the bar’s offerings without breaking the bank.

Smallest Bar is a must-visit for those seeking a taste of Key West’s history and charm. Whether you’re looking for a quiet drink, live music, or simply want to soak in the atmosphere, this historic bar has it all. So, make sure to add Smallest Bar to your Key West itinerary and experience a true slice of the island’s vibrant bar scene.

Speakeasy Inn & Rum Bar

Located in the heart of Key West, Speakeasy Inn & Rum Bar is a historic gem that transports visitors back to the days of Prohibition. This charming establishment offers a unique experience with its vintage decor, live music, and of course, an impressive selection of rum. Let’s dive into the details of what makes Speakeasy Inn & Rum Bar a must-visit destination for any history buff or rum enthusiast.

The History:

Speakeasy Inn & Rum Bar is housed in a historic building that dates back to the late 1800s. It was originally a boarding house for cigar makers and later became a speakeasy during the Prohibition era.
The building still retains its original architecture and charm, with exposed brick walls, wooden beams, and a cozy courtyard that adds to the ambiance.
As you step inside, you can almost feel the whispers of the past, imagining the secret dealings and hidden revelries that took place during the Prohibition era.

The Atmosphere:

The ambiance at Speakeasy Inn & Rum Bar is cozy and intimate. The dim lighting, vintage furnishings, and jazz music set the stage for an authentic speakeasy experience.
You’ll find yourself immersed in a relaxed and casual atmosphere, perfect for enjoying a quiet drink or engaging in lively conversations with fellow patrons.
Whether you choose to sit at the bar, at one of the cozy tables, or in the charming courtyard, you’re sure to feel transported to a bygone era.

The Rum Selection:

One of the highlights of Speakeasy Inn & Rum Bar is its extensive selection of rum. From light and fruity to dark and full-bodied, they have something to satisfy every rum lover’s palate.
The knowledgeable bartenders are more than happy to recommend a rum based on your preferences or suggest a signature co*cktail that showcases the flavors of the Caribbean.
Don’t miss the opportunity to try their rum flights, which allow you to sample a variety of rums and explore the nuances of each.

Live Music:

Adding to the ambiance, Speakeasy Inn & Rum Bar features live music performances on select nights.
Local musicians fill the air with the soulful sounds of jazz, blues, and other genres, creating a lively and entertaining atmosphere.
The combination of live music, delicious rum, and historic surroundings makes for an unforgettable evening at Speakeasy Inn & Rum Bar.

Speakeasy Inn & Rum Bar offers a unique and immersive experience for anyone seeking a taste of history and a love for rum. With its historic setting, cozy ambiance, impressive rum selection, and live music, it’s a destination that shouldn’t be missed when visiting Key West. So, step back in time and raise a glass to the bygone era of speakeasies at Speakeasy Inn & Rum Bar.

Green Parrot Bar

Welcome to Key West, where the sun is always shining and the drinks are always flowing! Today, we are going to take a closer look at one of the most iconic and historic bars in this vibrant city – the Green Parrot Bar. So grab a drink and let’s dive into the history and charm of this legendary establishment.

The Green Parrot Bar, located at 601 Whitehead Street, has been serving locals and visitors since it first opened its doors in 1890. With over 130 years of history, this bar has become a beloved institution in Key West and a must-visit destination for those seeking a taste of the city’s vibrant past.

As you step inside the Green Parrot Bar, you are immediately transported back in time. The interior is adorned with vintage photographs, old license plates, and quirky signs, creating a nostalgic atmosphere that is both welcoming and intriguing. The bar itself is made of rich mahogany, adding a touch of elegance to the space.

One of the highlights of the Green Parrot Bar is its impressive selection of drinks. From classic co*cktails to local craft beers, there is something to please every palate. Whether you’re in the mood for a refreshing mojito, a tangy margarita, or a cold pint of beer, the skilled bartenders at the Green Parrot Bar will mix up a drink that will leave you wanting more.

But it’s not just the drinks that make the Green Parrot Bar special – it’s the people. This bar has a reputation for attracting a diverse and friendly crowd. Whether you’re a local regular or a first-time visitor, you’ll feel like part of the family as soon as you walk through the door. The laid-back and unpretentious vibe of the Green Parrot Bar is a refreshing break from the hustle and bustle of the outside world.

When it comes to entertainment, the Green Parrot Bar has got you covered. Live music is a staple here, with talented musicians taking the stage seven nights a week. From blues and rock to reggae and country, you can expect an eclectic mix of genres that will get you grooving to the beat.

Now, let’s summarize what makes the Green Parrot Bar so special:

A rich history dating back to 1890
A nostalgic and welcoming atmosphere
An impressive selection of classic co*cktails and local craft beers
A diverse and friendly crowd
Live music seven nights a week

So, if you find yourself in Key West and want to experience a true piece of its history, make sure to stop by the Green Parrot Bar. You’ll be greeted with a warm smile, a cold drink, and memories that will last a lifetime.

Willie T’s

Willie T’s is a historic bar located in the lively and vibrant city of Key West, Florida. This iconic establishment has been serving locals and tourists alike for many years, and is known for its lively atmosphere, live music, and delicious drinks.

Here are some key features of Willie T’s that make it a must-visit destination:

Historic charm: Willie T’s is housed in a charming historic building, which adds to its unique and inviting ambiance. The bar has retained much of its original character, creating a nostalgic and authentic experience for patrons.
Live music: One of the highlights of Willie T’s is its live music performances. Talented musicians take the stage every night, playing a variety of genres including rock, reggae, and blues. The lively tunes create a fun and energetic atmosphere that keeps guests entertained throughout the evening.
Extensive drink menu: Willie T’s offers an extensive drink menu, catering to all tastes and preferences. From classic co*cktails to craft beers, there is something for everyone. The skilled bartenders are also known for their creative concoctions, so be sure to try one of their signature drinks.
Outdoor seating: Another great feature of Willie T’s is its outdoor seating area. Guests can enjoy their drinks and soak up the Key West sunshine on the spacious patio. This is a perfect spot for people-watching and enjoying the vibrant street scene.
Friendly staff: The staff at Willie T’s are known for their warm and friendly service. They create a welcoming and inclusive environment, ensuring that all guests feel comfortable and taken care of.

Whether you’re a history enthusiast, a live music lover, or simply looking for a fun night out, Willie T’s is a fantastic choice. Its historic charm, live music, extensive drink menu, outdoor seating, and friendly staff make it a bar that should not be missed when visiting Key West.

Capt Tony’s Saloon

If you are looking for a historic bar with a unique atmosphere in Key West, then Capt Tony’s Saloon is a must-visit destination. Located on Greene Street, this iconic bar has a rich history dating back to the 1850s.

Capt Tony’s Saloon was originally known as the First National Bank of Key West, but it was later converted into a saloon. Over the years, it has been a gathering place for sailors, fishermen, and locals alike.

Here are some reasons why Capt Tony’s Saloon stands out among the bars in Key West:

Historic Ambience: As soon as you step inside Capt Tony’s Saloon, you will be transported back in time. The bar has retained its original architecture, with its wooden floors, exposed beams, and rustic decor. The walls are adorned with old photographs and memorabilia, adding to the nostalgic atmosphere.
Live Music: Capt Tony’s Saloon is known for its live music performances. Talented local musicians take the stage every night, playing a mix of blues, rock, and country. The intimate setting allows you to enjoy the music up close and personal.
Famous Patrons: Over the years, Capt Tony’s Saloon has attracted many famous patrons, including Ernest Hemingway and Jimmy Buffett. Hemingway was a regular at the bar and even mentioned it in his novel “To Have and Have Not.” Jimmy Buffett also frequented Capt Tony’s Saloon and even played here before he rose to fame.
Affordable Drinks: Despite its historic status, Capt Tony’s Saloon offers reasonably priced drinks. Whether you prefer beer, wine, or co*cktails, you will find a wide selection at the bar. They also have daily drink specials, so you can enjoy your favorite beverages without breaking the bank.
Outdoor Patio: If you prefer to enjoy your drinks outdoors, Capt Tony’s Saloon has a charming patio where you can relax and soak up the Key West sunshine. This is a great spot to people-watch and take in the lively atmosphere of the surrounding streets.

Capt Tony’s Saloon is a historical gem in Key West that offers a one-of-a-kind experience. Whether you are a history enthusiast, a music lover, or simply looking for a good time, this bar will not disappoint. So, make sure to include Capt Tony’s Saloon in your Key West itinerary and create lasting memories at this iconic establishment.

Old Town Tavern & Beer Garden

Welcome to Key West, where the historic bars are as plentiful as the tropical drinks! As a professional sommelier, I have had the pleasure of exploring the vibrant bar scene in this charming city. Today, I want to take you on a journey to one of the most iconic establishments in Key West – Old Town Tavern & Beer Garden.

Located in the heart of Old Town, this lively bar is a must-visit for anyone seeking a taste of Key West’s rich history and laid-back atmosphere. Let’s dive into the details of what makes this place so special.

Ambiance

Old Town Tavern & Beer Garden exudes a cozy and welcoming ambiance, perfect for both locals and tourists alike. The interior is adorned with classic Key West memorabilia, vintage photographs, and rustic wooden furnishings that transport you back in time. Step outside into the beer garden, and you’ll find yourself surrounded by lush greenery and twinkling lights, creating a magical atmosphere for a memorable evening.

Drink Selection

As a beer lover’s paradise, Old Town Tavern offers an impressive selection of craft beers from both local and international breweries. Whether you prefer a refreshing lager, a hoppy IPA, or a rich stout, you’ll find something to satisfy your taste buds. The knowledgeable bartenders are always ready to recommend the perfect brew to suit your preferences.

Signature co*cktails

If beer isn’t your thing, fear not! Old Town Tavern also boasts a creative co*cktail menu that showcases the flavors of Key West. From the classic Mojito to the tropical Margarita, each drink is expertly crafted using the finest spirits and fresh local ingredients. Don’t miss out on trying their signature co*cktail, the Hemingway Daiquiri, inspired by the famous writer who frequented Key West.

Live Music

No visit to Old Town Tavern is complete without enjoying the lively tunes of talented local musicians. The bar hosts regular live music performances, ranging from acoustic sets to energetic bands that will have you dancing the night away. Check their schedule to see who’s playing during your visit, and get ready to experience the vibrant music scene of Key West.

Food Options

To complement your drinks, Old Town Tavern offers a delectable menu of pub-style fare. From juicy burgers to crispy fish tacos, their dishes are made with fresh ingredients and bursting with flavor. Whether you’re looking for a quick snack or a satisfying meal, you’ll find plenty of options to satisfy your cravings.

So, whether you’re a history buff, a beer enthusiast, or simply looking for a fun night out, Old Town Tavern & Beer Garden is a must-visit destination in Key West. Immerse yourself in the rich history, vibrant ambiance, and delicious drinks of this iconic establishment – you won’t be disappointed!

General Horseplay

Welcome to Key West, where history and entertainment meet in the form of charming bars and pubs. In this article, we will explore one of the most historic bars in Key West: General Horseplay.

General Horseplay, located at 423 Caroline Street, is a hidden gem that offers a unique and unforgettable experience for bar enthusiasts. This historic establishment has been serving patrons since 1934, making it one of the oldest bars in Key West.

As you step inside General Horseplay, you’ll immediately be greeted by its cozy and rustic atmosphere. The dimly lit space is adorned with vintage photographs, antique furniture, and old-fashioned decor, transporting you back in time to the Prohibition era.

The bar itself is a work of art, with a stunning wooden countertop that has witnessed decades of lively conversations and laughter. Pull up a stool and engage in friendly banter with the knowledgeable and friendly bartenders, who are always ready to serve you a perfectly crafted co*cktail.

General Horseplay offers an extensive selection of spirits, including a wide range of whiskey, rum, vodka, and gin. Whether you prefer a classic Old Fashioned or a creative concoction, the talented mixologists at General Horseplay will impress you with their skill and creativity.

If you’re a beer lover, General Horseplay has you covered as well. They offer a variety of craft beers on tap, showcasing the best local and regional breweries. From hoppy IPAs to rich stouts, there’s something to satisfy every beer enthusiast’s palate.

One of the highlights of General Horseplay is its live music performances. Step back in time as talented musicians take the stage, playing soulful blues, jazz, and rock ‘n’ roll tunes. The intimate setting allows you to truly connect with the music and immerse yourself in the vibrant atmosphere.

General Horseplay also hosts trivia nights and game tournaments, adding an extra layer of fun and excitement to your visit. Challenge your friends or make new ones as you compete for bragging rights and enjoy a night filled with laughter and friendly competition.

When it comes to food, General Horseplay offers a delicious menu of bar bites and comfort food classics. From crispy chicken wings to loaded nachos, these tasty treats perfectly complement your drinks and ensure that you won’t go hungry during your visit.

General Horseplay’s rich history, warm ambiance, skilled mixologists, live music, and exciting events make it a must-visit bar in Key West. Whether you’re a history buff, a co*cktail enthusiast, or simply looking for a fun night out, this historic establishment will exceed your expectations.

So, make sure to add General Horseplay to your Key West itinerary and step into a bygone era as you enjoy unforgettable drinks, lively music, and a warm and welcoming atmosphere.

Conclusion

Key West is a treasure trove of historic bars that offer a unique and immersive experience for visitors. These bars not only provide a glimpse into the rich history of the island but also serve as vibrant social hubs where locals and tourists can come together and create lasting memories.

From the iconic Sloppy Joe’s to the charming Green Parrot, each bar has its own distinctive character and story to tell. The laid-back atmosphere and friendly hospitality make these establishments a must-visit for anyone looking to soak in the island’s vibrant culture.

Whether you’re sipping on a refreshing co*cktail at Captain Tony’s Saloon, enjoying live music at The Bull and Whistle, or indulging in a delicious seafood feast at Schooner Wharf Bar, the historic bars in Key West offer something for everyone. The historic architecture, vintage decor, and memorabilia on display transport visitors back in time, providing a nostalgic ambiance that cannot be replicated elsewhere.

Moreover, the diverse range of bars caters to different preferences and interests. Whether you’re a fan of Hemingway and want to experience his favorite haunt at the Green Parrot, or you’re a lover of live music and want to dance the night away at Irish Kevin’s, there is a bar in Key West that will fulfill your desires.

In addition to their historical significance, these bars are also deeply ingrained in the local community. They have witnessed countless celebrations, gatherings, and stories over the years, becoming an integral part of the island’s cultural fabric. The sense of camaraderie and conviviality that permeates these establishments is truly infectious, making visitors feel like they are a part of something special.

So, if you find yourself in Key West, make sure to immerse yourself in the world of historic bars. Take a stroll down Duval Street and let the electric energy guide you to these hidden gems. Whether you’re a history buff, a co*cktail connoisseur, or simply someone seeking a memorable night out, the historic bars of Key West will not disappoint. They are a testament to the island’s enduring spirit and will leave you with a deep appreciation for its rich heritage.

Exploring Key West's Historic Bars - Summer Stirs (2024)