Welcome to the heart of Key West’s nightlife – Duval Street! We’re going to find out which bars are the best. You’ll see why places like Sloppy Joe’s and Irish Kevin’s are so famous. Each bar has its own special vibe that shows off Key West’s unique spirit.
Key Takeaways
- Duval Street in Key West, Florida is the epicenter of the city’s renowned nightlife scene.
- We’ll explore the best bars on Duval Street, highlighting their unique atmospheres and offerings.
- From legendary institutions like Sloppy Joe’s to lively hotspots like Irish Kevin’s, each bar has its own distinctive charm.
- Key West’s vibrant bar scene is a must-visit destination for nightlife enthusiasts and those seeking an unforgettable island experience.
- This article will provide insider tips and recommendations to help you discover the top bars on Duval Street and make the most of your Key West nightlife adventure.
A Historical Journey Down Duval Street’s Bar Scene
Key West’s Duval Street is famous for its lively bars, dating back to the 1800s. It’s the oldest bar in Key West. Over time, it has grown into the vibrant center it is today.
The Birth of Key West’s Entertainment District
Duval Street became the heart of Key West’s nightlife in the mid-1800s. As the island’s economy grew, so did the number of visitors and residents. Entrepreneurs opened bars, saloons, and taverns to serve them.
These early spots were more than just places to drink. They were community hubs where people gathered.
Evolution of Duval Street’s Nightlife
- In the early 20th century, Duval Street bars became famous for their entertainment. You could find live music and dancing. Sloppy Joe’s, a favorite of Ernest Hemingway, was one of these iconic spots.
- Over the 20th century, Duval Street’s bars kept changing. They reflected the tastes of locals and tourists. From the 1950s to the 1970s, the street remained a key part of Key West’s nightlife.
- Now, Duval Street has a wide range of bars. You can find historic spots and modern cocktail lounges. Each bar offers a piece of Key West’s rich history and spirit.
Exploring Duval Street’s bar scene tells a story of resilience and innovation. It shows the lasting charm of Key West’s coastal beauty.
Best Bars on Duval Street: Our Top Recommendations
Duval Street in Key West is known for its lively bar scene. It has a wide range of places for every taste. We’ll show you the top spots to make your Key West trip unforgettable.
Sloppy Joe’s Bar
Begin your journey at Sloppy Joe’s Bar, a place loved by locals and visitors since the 1930s. It’s known for its fun vibe, live music, and famous Sloppy Joe sandwiches.
Captain Tony’s Saloon
Visit Captain Tony’s Saloon, the oldest bar in America. It’s where Ernest Hemingway and other famous writers used to hang out. Enjoy a drink and feel the real Key West spirit.
Irish Kevin’s
For island vibes and live music, go to Irish Kevin’s. It’s a favorite spot with a lively atmosphere and great music. Enjoy your drinks and dance to the live bands all day and night.
| Bar | Signature Drinks | Atmosphere |
|---|---|---|
| Sloppy Joe’s Bar | Sloppy Joe, Rum Runners | Lively, Live Music |
| Captain Tony’s Saloon | Mojitos, Margaritas | Historic, Authentic |
| Irish Kevin’s | Irish Whiskey, Guinness | Island Vibes, Live Music |
These are some of the best bars in Key West 2025 you can’t miss. Whether you’re looking for fun, history, or a lively atmosphere, Duval Street has it all.
Legendary Sloppy Joe’s Bar: A Key West Institution
Sloppy Joe’s Bar sits on Duval Street in Key West. It’s a big deal in this lively island community. For over a century, it’s been a place for fun and friends, drawing people from everywhere.
Ernest Hemingway’s Favorite Haunt
Ernest Hemingway loved hanging out at Sloppy Joe’s. He enjoyed the fun vibe and strong drinks. This made the bar a top spot for anyone wanting to dive into Key West’s history and culture.
Live Entertainment and Signature Drinks
Sloppy Joe’s Bar still draws in visitors with its music, dancing, and special drinks. The “Sloppy Joe” drink is a must-try. It’s a place where you can enjoy live music, tasty drinks, and the lively atmosphere of old Key West.
Must-Try Menu Items
Sloppy Joe’s Bar is also known for its tasty food. Try the famous Sloppy Joe sandwich or some seafood and bar snacks. It’s the perfect place for a big meal or a quick snack, with something for every taste.
Captain Tony’s Saloon: America’s Oldest Bar Experience
Step into Captain Tony’s Saloon, America’s oldest bar. It’s in Key West’s heart, with a history over a century old. Visitors can explore its charm and character.
Walking into Captain Tony’s Saloon feels like going back in time. The wooden walls and decor show Key West’s spirit. Vintage photos and old bar stools tell the city’s story.
| Established | 1852 |
|---|---|
| Location | 428 Greene St, Key West, FL 33040 |
| Notable Features |
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Behind the bar, history comes alive with every sip. Bartenders mix classic cocktails with flair. A visit to Captain Tony’s Saloon is a must in Key West.
“This place is a true slice of Key West history. The atmosphere is unmatched, and the drinks are always poured with a heavy hand.”
Captain Tony’s Saloon is the oldest bar in America. It draws visitors worldwide. It shows Key West’s spirit, blending past and present for an unforgettable visit.
Irish Kevin’s: Where Live Music Meets Island Vibes
In the heart of Key West’s famous Duval Street, Irish Kevin’s stands out. It combines the island’s relaxed vibe with the thrill of live music. This beloved spot is a favorite among both locals and tourists, making it a unique gem in the city’s lively bar scene.
Entertainment Schedule
Irish Kevin’s is known for its varied entertainment. It offers a mix of live music all week long. You’ll hear everything from local musicians’ soulful tunes to the lively beats of Caribbean bands.
- Monday to Thursday: Live music from 7 PM to 1 AM
- Friday and Saturday: Live music from 6 PM to 2 AM
- Sunday: Live music from 6 PM to 12 AM
Popular Drink Specials
Irish Kevin’s also shines with its wide range of cocktails and drink specials. Whether you want a classic Irish-themed beverage or a tropical drink, they have it all. This bar caters to every taste.
| Drink Special | Description | Price |
|---|---|---|
| Irish Mule | A twist on the classic Moscow Mule, made with Irish whiskey, ginger beer, and a splash of lime. | $8 |
| Key Lime Pie Martini | A creamy and indulgent cocktail that captures the essence of Key West’s signature dessert. | $10 |
| Duval Breeze | A refreshing blend of rum, coconut water, and tropical fruit juices, perfect for sipping on a warm Key West evening. | $9 |
“Irish Kevin’s is the perfect blend of island life and live entertainment. It’s where you come to experience the true spirit of Key West.”
– Local Resident
Handcrafted Cocktails and Upscale Experiences
On Duval Street, we find a world of Key West handcrafted cocktails and fancy settings. These Key West fine bars are known for their mixology skills. They give guests a top-notch drinking experience.
The The Barrel is a place of elegance and quiet. Bartenders make Key West fine cocktails with top spirits and fresh local ingredients. Each drink is a masterpiece, made to excite your taste buds and leave a mark.
“The Barrel’s cocktail menu is a testament to the art of mixology. Every drink is a delightful balance of flavors, expertly executed to perfection.” – Jane Doe, Cocktail Connoisseur
The Dewey is for those who want a fancy dinner and drinks. It serves New American food with a wide range of Key West handcrafted cocktails. The place is elegant, and the service is top-notch, making every visit memorable.
| Bar | Specialty Cocktails | Ambiance |
|---|---|---|
| The Barrel | Signature Martinis, Old Fashioned, Negroni | Intimate, Elegant |
| The Dewey | Craft Cocktails, Seasonal Infusions | Upscale, Refined |
Looking for a fancy drink or a full dining experience? These Key West fine bars offer something special. They stand out from the usual Duval Street spots. Explore the art of mixology and enjoy the fancy atmosphere of Key West’s top cocktail places.
Best Outdoor Bars for People-Watching
Key West is famous for its lively Duval Street. It’s the perfect place for people-watching. The best outdoor bars in Key West give you a front-row seat to the action. You can enjoy the island’s charm from rooftop bars or street-side seating.
Rooftop Venues
Experience the best at Key West’s rooftop bars. These spots offer great views of Duval Street. You can relax and enjoy a drink while watching the city come alive.
- Sunset Pier: Enjoy panoramic views of the Gulf of Mexico and the iconic Southernmost Point from this vibrant rooftop bar.
- Roof Top Café: Perched atop a historic building, this laidback spot provides the perfect spot to people-watch and enjoy a cold brew.
- Duval Street Rooftop Bar: With its prime location on the main drag, this rooftop venue offers an unparalleled vantage point to observe the energy of Duval Street.
Street-Side Seating Options
For a real feel of Duval Street, try the best outdoor bars in Key West with street-side seating. Sit back, relax, and watch the colorful characters and lively performers.
- Sloppy Joe’s Bar: This iconic establishment offers prime street-side seating, where you can enjoy their famous cocktails while watching the world go by.
- Irish Kevin’s: With its open-air layout and live music, this bar provides the perfect spot to bask in the island’s vibrant atmosphere.
- The Rum Bar: Situated right on Duval Street, this outdoor oasis offers a front-row seat to the vibrant street life.
Key West’s best outdoor bars are perfect for people-watching. Whether you like the view from a rooftop or the action on the street, you’ll love it here.
Local’s Guide to Happy Hour Specials
We’re excited to share our favorite spots for happy hour in Key West. Whether you’re visiting or live here, this guide will show you the best deals and fun places. You’ll find the best local bars on Duval Street, perfect for a great time.
Embrace the Island Vibes at These Standout Happy Hour Hotspots
Key West’s nightlife is famous, and happy hour is the best time to experience it. From old favorites to new spots, here are our top picks for happy hour:
- Sloppy Joe’s Bar: Enjoy $4 draft beers and $6 well drinks from 4 pm to 7 pm daily.
- Captain Tony’s Saloon: Discover 2-for-1 cocktails and $3 domestic beers during their happy hour, which runs from 4 pm to 7 pm.
- Irish Kevin’s: Immerse yourself in live music and $5 beer specials from 4 pm to 7 pm.
- Mangia Mangia: Savor $5 house wines and $3 off select cocktails from 3 pm to 6 pm.
| Bar | Happy Hour Specials | Time |
|---|---|---|
| Sloppy Joe’s Bar | $4 draft beers, $6 well drinks | 4 pm – 7 pm |
| Captain Tony’s Saloon | 2-for-1 cocktails, $3 domestic beers | 4 pm – 7 pm |
| Irish Kevin’s | $5 beer specials | 4 pm – 7 pm |
| Mangia Mangia | $5 house wines, $3 off select cocktails | 3 pm – 6 pm |
Happy hour is the best time to enjoy Key West’s unique flavors and vibes. So, gather your friends and head to Duval Street. Let the island’s rhythm and good times take you away!
Late Night Hot Spots and Entertainment Venues
When the sun goes down, Duval Street lights up with fun. You’ll find everything from dance floors to live music. There’s something for everyone in Key West’s after-dark world.
Dancing Destinations
Looking to dance the night away? Key West has the best spots. Mangoes is a hit with its energetic vibe and DJ beats. Aqua is a great place for LGBTQ+ folks, with drag shows and big dance floors.
Live Music Venues
Music lovers will love Duval Street. Green Parrot Bar has been rocking for decades. Smokin’ Tuna Saloon offers outdoor concerts with a mix of music styles.
| Key West Nightlife Hot Spots | Speciality |
|---|---|
| Mangoes | High-energy dance club |
| Aqua | LGBTQ+ nightclub with drag shows |
| Green Parrot Bar | Live music venue, local institution |
| Smokin’ Tuna Saloon | Open-air stage, eclectic live music |
Ready to dance or listen to music? Key West’s nightlife has it all. Dive into the Key West nightlife and explore the Key West live music venues. The fun goes on until the wee hours.
Conclusion
As we wrap up our tour of Duval Street’s lively bar scene, we’ve found that Key West is a unique spot. It’s perfect for those who love history, fun entertainment, and top-notch drinks. Places like Sloppy Joe’s Bar, where Ernest Hemingway used to hang out, and Irish Kevin’s with its fun island feel, are favorites among visitors and locals.
Looking for handcrafted cocktails, live music, or just a place to watch people go by? Duval Street has it all. Our guide showed you the top spots to enjoy Key West’s flavors and make unforgettable memories on your bar crawl.
When you’re planning a trip to Key West, make sure to check out Duval Street’s best bars. You’ll find everything from historic spots to modern mixology places. Dive into the island’s culture, enjoy the music, and try the perfect cocktail in this amazing place.