Best Happy Hour Spots in Key West: A 1000-Word Guide to Sipping in Paradise
When the tropical sun begins to dip low over the turquoise waters surrounding Key West, the island truly comes alive with happy hour vibes. From waterfront tiki bars to chic cocktail lounges tucked away on quiet streets, Key West offers a rich mix of laid-back, island-style happy hours that blend affordability with the kind of unforgettable ambiance you can only find in the Florida Keys. Whether you're a connoisseur of rum runners, a lover of fresh seafood tapas, or just chasing that perfect sunset drink, this guide to the best happy hour spots in Key West will help you sip your way through paradise.
1. Alonzo’s Oyster Bar – Seafood & Waterfront Views
📍 700 Front Street, Key West
One of the most beloved and well-known happy hour destinations in Key West is Alonzo’s Oyster Bar, located at the A&B Marina. From 4 to 6:30 PM daily, Alonzo’s offers half-off appetizers and discounted drinks, including wine, beer, and well cocktails. But what really draws the crowd is the fresh seafood—from peel-and-eat shrimp to crispy calamari, mussels, and raw oysters.
Pair your chilled beer with the salty sea breeze as boats drift by just a few feet from your table. The location is perfect for anyone wanting to kick off their evening with harbor views and unbeatable shellfish.
2. The Waterfront Brewery – Craft Brews & Casual Vibes
📍 201 William Street, Key West
A favorite for craft beer lovers, The Waterfront Brewery offers happy hour deals from 4 to 6:30 PM, Monday through Friday. Expect discounted house brews, including their signature "Crazy Lady" blonde ale and “Island Life” lager. Beer aside, you’ll find $5 wines, well drinks, and great deals on bites like fish tacos, ahi tuna nachos, and fried pickles.
The lively, open-air venue sits right on the harbor, and upstairs you’ll find old-school arcade games and panoramic views of the marina. It’s a great casual spot to catch the sunset with a cold one in hand.
3. Bagatelle – Upscale & Romantic Happy Hour
📍 115 Duval Street, Key West
For a touch of elegance on Duval Street, head to Bagatelle, a charming historic home-turned-restaurant. From 4 to 6 PM daily, Bagatelle’s happy hour offers half-off all appetizers and drinks at the bar, including craft cocktails made with fresh-squeezed juices.
Highlights include lobster mac and cheese, tuna tartare, and crispy pork belly sliders. The cozy, romantic second-floor balcony is ideal for couples or small groups who want something a little more refined without losing the island charm.
4. Lucy's Retired Surfers Bar & Restaurant – Party Atmosphere
📍 320 Grinnell Street, Key West
Looking for a high-energy happy hour to start the night right? Lucy’s Retired Surfers Bar serves up a party atmosphere along with $6 margaritas, $5 drafts, and $6 specialty cocktails from 4 to 6 PM, Monday through Friday.
The surf-themed decor and upbeat music make this the perfect place to kick off your Duval Street crawl. Add in shrimp tacos, gator bites, and their addictive voodoo wings, and you’ve got a classic Key West happy hour spot with a side of funk and fun.
5. Conch Republic Seafood Company – A Key West Staple
📍 631 Greene Street, Key West
No happy hour list would be complete without the iconic Conch Republic Seafood Company. Overlooking the historic seaport, this legendary spot offers happy hour from 4 to 7 PM, with discounted drinks and appetizers.
The open-air setting, complete with dock views and nightly live music, makes this an ideal stop for both locals and tourists. Don’t miss the cracked conch, ceviche, and mojitos. It’s quintessential Key West—laid-back, welcoming, and full of island spirit.
6. First Flight Island Restaurant & Brewery – Aviation History Meets Happy Hour
📍 301 Whitehead Street, Key West
Housed in the original Pan Am Airways office building, First Flight blends aviation history with a lush garden patio and tropical cocktails. Happy hour runs from 4 to 6 PM, and includes $5 beer, half-off select appetizers, and signature cocktails like the “Conch Flyer.”
Sip under banyan trees surrounded by aviation relics, and sample snacks like fish dip, sliders, and conch fritters. It’s a quieter, more unique setting perfect for those who want a break from the bustle of Duval.
7. El Meson de Pepe – Cuban Flavors at Mallory Square
📍 410 Wall Street, Key West
Located next to Mallory Square, El Meson de Pepe serves up Cuban cuisine with a Key West flair. Their happy hour, from 4 to 6 PM daily, includes mojitos, rum punches, and house sangria, plus $6 tapas like tostones, empanadas, and croquetas.
It’s an excellent spot to enjoy a drink before the iconic sunset celebration just steps away. Live salsa and Latin jazz are often part of the evening’s entertainment, adding rhythm to your rum-fueled relaxation.
8. Green Parrot Bar – No-Frills Classic
📍 601 Whitehead Street, Key West
If you’re in the mood for something with a little more grit and local flair, The Green Parrot is a Key West institution. While it doesn’t have a formal happy hour, the affordable drink prices and legendary atmosphere make it a great stop any time of day. It's especially popular with locals looking for a cold beer and live music.
Grab a cheap draft or strong cocktail, lean back under the whirring ceiling fans, and let the blues, rock, or reggae set the tone. It’s the anti-tourist bar that somehow everyone finds—and no one forgets.
9. Blue Heaven – Chill, Colorful Backyard Drinks
📍 729 Thomas Street, Key West
Blue Heaven is more than just a restaurant—it’s a tropical hideaway. Their bar area offers an informal happy hour vibe, especially if you catch the live acoustic sets in the garden. Though there's no official happy hour menu, you can enjoy casual cocktails, Key West-style snacks, and a stunning, eclectic atmosphere under the trees, with roosters strutting nearby.
It’s perfect for those wanting to ease into the night with a relaxed, artsy atmosphere.
Conclusion: Find Your Happy Hour Heaven in Key West
From classy seafood havens to dive bars with soul, the happy hour scene in Key West is as diverse and colorful as the island itself. Whether you’re a visitor looking to enjoy your first rum punch with ocean views, or a seasoned traveler in search of local favorites, there’s a perfect happy hour for every kind of drinker and diner. Plan your evening around these hand-picked spots, and let Key West’s laid-back charm, delicious drinks, and salty breezes do the rest.
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