Alan Jackson and Jimmy Buffett famously sang that it’s 5 o’clock somewhere so pour them a drink. In Key West, happy hours - that time of the day when specials on drinks and food prevail - don’t always take place in the evening.
From super casual watering holes and seaside bars to elegant dining spots, happy hours rule in the Southernmost City. So belly up to the bar, catch the sunset and raise a glass to these discounted specials.
Here’s a list of Key West spots that offer cheap drinks and eats during their own versions of “Happy Hour.”
General Horseplay Cocktails and Tomfoolery
This place is home to cocktails named the Samurai, I Pity a Fool, and the Elegantly Disheveled. They have a daily happy hour from 3 to 6 p.m. where you roll a die to see what you’ll pay. Fours, fives and sixes mean full price but if you roll smaller you could be drinking for $1, $2 or half price of any drink under $20.
423 Caroline St.
First Flight Brewery
From 4 to 6 p.m. daily you can get house made beers and glasses of wine, including pinot grigio, chardonnay, cabernet and malbec, for $5 a glass and half off selected cocktails. Their happy hour menu consists of $5 plates of beef brisket mac and cheese, tuna poke wontons and “devil eggs,” that feature fried jalapeños.
301 Whitehead St.
Mary Ellen’s Bar and Restaurant
This place proclaims its happy hour the best in Key West. For starters, it runs from noon to 6 p.m. Monday through Friday. The drink specials? Try 2-for-1 draft beers, cocktails, wine and well drinks, or $2 off Jameson-made frozen Irish coffees or straight-up $5 glasses of Jameson whiskey. From 3 to 6 p.m., get $5 comfort foods like a classic grilled cheese, “Jonci’s Fried Mushrooms,” or cheesy tater tots.
420 Appelrouth Lane at Duval St.
Conch Republic Seafood Company
Locals call it the “Conch Farm,” and it has seaport views along with outdoor seating and a chummy social scene. They’ll sell you 2-for-1 beers of all kinds - domestic, imports and craft - or 2-for-1 house wines or 2-for-1 premium well drinks daily from 4 to 7 p.m. But happy hour is served at the bar or on the patio only.
631 Greene St.
Blue Macaw Island Eats and Bar
This colorful spot with outdoor dining and drinking in Key West’s historic Bahama Village is just a short walk from Duval Street. Live music is a staple of the business. Happy hour is from 4 to 7 p.m. daily and features $3 bottle beers, $3 well drinks, $3 wines and half off appetizers.
804 Whitehead St.
Thirsty Mermaid
The Thirsty Mermaid focuses as much on food as they do on drink specials. From 4 to 6 daily, enjoy $2 pints of their private label Mermaid Lager and $5 plates of a half dozen Apalachicola oysters, the ceviche du jour and mac and cheese croquettes.
521 Fleming St.
Pepe’s Cafe and Steakhouse
This eatery offers hearty cooking like a “Thanksgiving sandwich,” baked oysters, burgers and a steak “smothered in pork chops,” but also indulges in a happy hour from 4 to 6 p.m. daily with $6 fresh-squeezed margaritas, half off oysters and $1.50 Yuengling brews, along with other discounted wines, well drinks and select domestic bottles.
806 Caroline St.
Half Shell Restaurant and Bar
This place at the Historic Key West Seaport has a happy hour from 4:30 to 6:30 daily with half off all well drinks, beer and house wines, along with oysters by the dozen for $10 and beer-steamed shrimp by the pound for $17.50.
231 Margaret St.
Bourbon Street Pub
On the wilder side, the New Orleans-themed club Bourbon Street Pub is known for its outdoor pool area - which has a Saturday clothing optional parties for all genders - drag shows and many theme nights. They don’t have a happy hour per se, but on Friday nights, it’s where the locals hide from the tourists for the “Bourbon Tea.” All are welcome on Fridays from 5 to 8 p.m. for DJ Rude Girl’s spinning and $6 Stoli drinks. They also have a ladies night every Tuesday from 5 p.m. to midnight and after 8 p.m., women get $ well drinks and beer and wine.
724 Duval St.
Old Town Tavern and Beer Garden
Check out their two daily happy hours from 4 to 7 p.m. and 11 p.m. to 1 a.m. with half off wines and well drinks and 25 percent off all beer, plus half off flatbreads and shared plates.
900 Duval St.
Tavern N Town
Located at the Key West Marriott Beachside hotel, this is a locals’ favorite with, count ‘em, three happy hours daily. A breakfast happy hour starts the day from 8 to 11 a.m. daily with 2-for-1 bloody mars, mimosas and screwdrivers. From 5 to 7 p.m. and 9 to 11 p.m., you may partake of 2-for-1 drink specials.
3841 N. Roosevelt Blvd.
La Te Da
This hotel, cabaret and restaurant with the outdoor and indoor bar, has happy hour Monday through Friday from 4 to 6:30 p.m. They offer half off all cocktails and a $5 bar snack menu.
1125 Duval St.
This story was originally published March 08, 2019 5:42 PM.
%20Cropped%20(1).jpg)