Evening Drinks on Duval Street, Key West

 

Evening Drinks on Duval Street, Key West: Where to Sip, Savor, and Soak in the Vibes

Duval Street is the pulsing heart of Key West. Stretching from the Gulf of Mexico to the Atlantic Ocean, this iconic street is a lively blend of energy, music, history, and island charm. While it's famous for its eclectic shops and colorful crowd, Duval Street truly comes alive in the evening — when the sun begins to dip and the bars and lounges swing open their doors to a flood of thirsty travelers and laid-back locals. Whether you're in search of a tropical cocktail, a dive bar with personality, or an elegant wine bar, Duval Street has it all. Here’s a guide to the best spots for evening drinks on this legendary stretch.

1. Sloppy Joe’s Bar – The Hemingway Haunt

No visit to Duval Street is complete without a stop at Sloppy Joe’s, the world-famous bar that was once frequented by Ernest Hemingway. With its long history dating back to 1933, this Key West institution blends nostalgia with a party vibe. The bar offers an impressive list of cocktails, draft beers, and rum punches, along with live music that kicks in nightly.

What to order: The Sloppy Rita (a house margarita with a Hemingway twist) or their signature Sloppy Joe Lager.

Vibe: Lively, casual, and always buzzing with energy.

2. The Green Parrot – A No-Frills Local Favorite

Located just off Duval on Whitehead Street (but still a vital part of the scene), The Green Parrot Bar is Key West’s oldest bar and one of its most beloved. There’s no glitz here — just cold drinks, live blues or reggae bands, and a diverse crowd.

What to order: Their legendary Rum Runner or a cold local craft beer.

Vibe: Gritty, authentic, and incredibly fun — perfect for those who like their drinks with a dose of character.

3. The Rum Bar at the Speakeasy Inn – Small Bar, Big Flavor

Nestled inside a historic 1800s building, The Rum Bar is a hidden gem for those seeking handcrafted cocktails and a break from the larger crowds. It may be small, but its collection of over 250 rums is mighty.

What to order: A Hemingway Daiquiri or a handcrafted Painkiller made with Pusser’s rum.

Vibe: Cozy, intimate, and friendly — ideal for rum lovers and connoisseurs.

4. Captain Tony’s Saloon – The Original Sloppy Joe’s

Before Sloppy Joe’s moved to its current location, it lived in this iconic building that now houses Captain Tony’s Saloon. The floor is covered in dollar bills, the ceiling holds bras and business cards, and the stories are as strong as the drinks.

What to order: A classic rum punch or a frozen piña colada.

Vibe: Old-school, legendary, and packed with wild stories — this is Key West at its most colorful.

5. The Porch – Craft Beer and Artisan Wines

For a more relaxed and upscale evening drink, The Porch is a fantastic alternative to the louder bars on Duval. Housed in a stunning Victorian mansion, The Porch specializes in craft beers, unique wines, and creative cocktails. The atmosphere is artsy, and the porch seating under the swaying palms is unforgettable.

What to order: A Florida craft IPA or a tropical sangria.

Vibe: Chill, artsy, and inviting — a perfect pre-dinner drink spot or a quiet nightcap location.

6. Fat Tuesday – Frozen Fun in a Cup

Sometimes, you just want a sweet, boozy slushie in your hand as you stroll Duval. That’s where Fat Tuesday comes in. Known for its colorful frozen daiquiris and party vibe, it’s a must-stop if you’re looking to cool down with a cold buzz.

What to order: The 190 Octane (an orange-flavored, high-proof beast) or the Category 5 Hurricane.

Vibe: Fun, loud, and made for people-watching.

7. Aqua Bar and Nightclub – Drag Shows and Signature Cocktails

If you're up for evening entertainment with your drink, Aqua is the place to be. Known for its wildly popular drag shows and themed nights, Aqua offers not only excellent performances but a full bar with expertly made cocktails.

What to order: A spicy margarita or any drink from their rotating themed specials menu.

Vibe: Energetic, inclusive, and wildly entertaining.

8. First Flight Island Restaurant & Brewery – A Toast to Aviation

Located in the birthplace of Pan American Airways, First Flight is both a restaurant and microbrewery, with an inviting beer garden under twinkling lights. It’s an ideal place to enjoy a craft beer flight before moving on to livelier venues.

What to order: Any of their in-house brews — especially Havana Red or Main Squeeze.

Vibe: Historical, relaxed, and perfect for aviation buffs or beer lovers.

9. Rick’s & Durty Harry’s Complex – A Bar-Hopper’s Paradise

If variety is what you're after, Rick’s and Durty Harry’s is an 8-bar mega complex with everything from a live rock band venue to an upstairs dance club. It’s easy to get lost — in a good way.

What to order: A frozen rum runner from the downstairs tiki bar or a cold beer at the open-air lounge.

Vibe: Diverse, high-energy, and great for groups who can’t decide on one vibe.

10. La Te Da – Rooftop Glamour and Sophistication

La Te Da Hotel and Bar is more than a drinking destination — it’s an experience. Their cabaret shows are famous, the piano bar is legendary, and the drinks are top-notch. The rooftop terrace offers one of the classiest places for a sunset drink on the island.

What to order: A Key Lime Martini or a crisp glass of rosé.

Vibe: Elegant, theatrical, and just the right amount of glam.

Final Sip: Tips for Enjoying Duval Street Evenings

• Pace Yourself: With so many tempting spots, it’s easy to go overboard. Hydrate between drinks and consider a food stop or two along the way.

• Tip Generously: Bartenders in Key West are some of the best — show them appreciation.

• Stay Safe: Most places are within walking distance, and taxis or pedicabs are readily available.

Conclusion

Evening drinks on Duval Street are more than just cocktails and cold beers — they’re a rite of passage in Key West. Whether you’re sipping something tropical under the stars, jamming to live music, or soaking up the stories of iconic bars, there’s a flavor and a memory waiting for everyone. So raise your glass to the good times and dive into the unforgettable nightlife of Duval Street. Cheers!