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Best Places for Happy Hour in Key West

Famous for the raucous nightlife of Duval Street, Key West is no doubt a drinking town that attracts visitors from all walks of life. The good news is, it’s easy to drink – and even eat – on the cheap with killer happy hour specials across the island. You can also purchase a Key West Bar Card for $27, which gives you one 2-for-1 drink at 14 participating bars per day at any hour. The card is good for an entire year, so it’s an even better value if you visit Key West regularly or call the island home. Read on for the best places to spend a happy hour in Key West.

Conch Republic Seafood Company

Photo Credit: Conch Republic Seafood Company

Conch Republic Seafood Company
When: 4-7pm Daily
What: 2-for-1 beer, wine and premium well drinks
The Conch Republic Seafood Company (aka The Conch Farm to locals) has one of the best happy hours going. The open-air establishment overlooks the Historic Seaport and features live music daily to get the party started.

Alonzo’s Oyster Bar
When: 4-6pm Daily
What: Half price appetizers and drinks
You can easily make a meal of happy hour at Alonzo’s Oyster Bar. Located on the Historic Seaport, grab an outside table for prime views. The entire appetizer page of the menu is half off, so load up on peel ‘n eat shrimp, oysters Rockefeller, buffalo shrimp, potato cakes, calamari and more. Wash it down with half price drinks (they make a killer ginger mojito) and you’re all set.

Kelly’s Caribbean

When: 4-7pm Daily
What: $5.95 Wings, $4.50 Key Lime Margarita, $2 Microbrews
Kelly’s is a classic happy hour spot. With specials on delectable wings (some say they’re the best on the island) and heavenly Key Lime Margaritas, you can fill up on the cheap at this charming outdoor patio bar shaded by banyan trees.

El Meson de Pepe

Photo Credit: El Meson de Pepe

El Meson de Pepe
This authentic Cuban restaurant serves up fresh, homemade mojitos and other tasty cocktails throughout the day. Stop by during lunch for a Cuban sandwich and cerveza or enjoy small bites like conch fritters, guacamole and tostones rellenos with a glass of wine for dinner. Located in the heart of Mallory Square, El Meson de Pepe offers a beautiful vantage point of the nightly sunset celebration. Ask to be seated on their outside patio and watch as the sun slips below the horizon while enjoying live music from 6-10 pm.

Rick’s is an eight bar entertainment and party complex in the middle of famed Duval Street. The drink specials are just as various at the setting itself with something different being offered every night of the week. Fridays boast $5 martinis in the Loft from 9-11pm. Tuesday Boozeday offers two $6 drinks for $8 and Jager is $4 all day every day. Ask the bartender about the nightly specials.

When: Monday Nights
What: $5 Martini Monday
Martini Monday at Virgilio’s is an institution in Key West. With an expansive menu of martinis from creative concoctions like espresso and key lime pie to more traditional dry and dirty varieties, you’re sure to find a favorite. The indoor/outdoor space also hosts a live band for Martini Monday that really gets the crowd grooving.

Island Dogs

Photo Credit: Island Dogs Bar

Island Dogs
When: 4:30-6:30pm Daily
What: Half off well drinks, bottled beer, house wine and oysters. $5.95 appetizer menu including conch fritters, fried zucchini and buffalo popcorn shrimp.
Island Dogs is a great spot to fill up on delicious appetizers and refreshing drinks at discounted happy hour rates. With a breezy patio and open concept, there’s plenty of space to unwind in this laidback bar with a sleek design.

Galleon Resort Sunset Tiki Bar
When: 10am-12pm Daily & 4-7pm Daily
What: 2-for-1 Bloody Mary’s in the morning and 2-for-1 Margaritas in the evening.
Although it’s located at a harbor front resort, the Sunset Tiki Bar at the Galleon attracts a lot of Key West locals. With a poolside setting and great views of the channel, this is an off-the-beaten path spot to enjoy the sunset away from the crowds at Mallory Square.

Agave 308
When: 4:30-6:30pm Daily
What: $6 Specialty Margaritas and $2-$3 Beers
Dedicated to agave and its many varieties of mezcal and tequila, Agave 308 boasts some of the most impressive cocktails on the island. During happy hour, a generous number of specialty margaritas are discounted, including a spicy jalapeno margarita, passion fruit margarita and the Mayan mojito made with tequila.

Lazy Gecko
When: 5-8pm Daily
What: 2-for-1 drinks and $1 off frozen drinks
It’s always a party at the Lazy Gecko, so get here early for the daily happy hour. The vibe gets more high energy as the night progresses with a DJ and dancing, but happy hour usually calls for live music and a laidback scene.

Fury Key West Sunset Sail

Photo Credit: Fury Water Adventures

Fury Water Adventures
Looking for an out of the ordinary happy hour that offers good drinks and an even better view of Key West? Hop aboard a sunset sail from Fury Water Adventures and leave the hustle and bustle of Key West behind, if only for a few hours. Choose from a variety of options, from the classic sail to live music performed by Key West locals, The Cory Heydon Band. There’s nothing more relaxing than ending another day in paradise with a cold margarita as you sway to the rhythm of the music. And for those who’d like to spend more time on the water, combine a sunset sail with select other trips like the glass bottom boat, snorkeling and Local’s Eco Tour.