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We all know the legendary Alan Jackson and Jimmy Buffett song “It’s 5 o’clock Somewhere” and in Key West, it’s pretty much 5 o’clock All. The. Time. That’s right! Key West IS the ultimate Happy Hour…and here is the ultimate Happy Hour list. Come drink with me — from A to Z — with the Key West Happy Hour Guide! Complete with website links, locations, times AND specials, here are nearly 50 watering holes, bars, restaurants and fine dining establishments with food, drink and an island breeze sure to please! Bookmark this page for future reference (Heck! Print it out and put it in your back pocket!) and begin your very own (on or off) Duval Crawl! Cheers! 🍹✨🍹
But first…a Legend!
🌴🙌🏼🌴 – “Palms Up!” This one is a “Sherri in Paradise” pick! A definite fave for frequenting!
🌴👩🏻🦰🌴 – I’ve been! Ask me anything!
🌴🚘🌴 – I consider hitching a ride to this one. I love to walk and bike, but these are establishments further away from the island centre. Grab a taxi, Uber, or scooter!
Ready. Set. HAPPY!
Alonzo’s 🌴👩🏻🦰🌴
700 Front St.
4-6 p.m.
Half-price appetizers
Aqua 🌴👩🏻🦰🌴
711 Duval St.
2-6 p.m.
$5 well drinks / $3.75 domestic beers
Bagatelle 🌴🙌🏼🌴
115 Duval St.
9-11:30 a.m. Breakfast Hangover
4-6 p.m. Afternoon Happy Hour
Half-price drinks / $5 appetizers
Better Than Sex
926 Simonton St.
Thursdays (All Night)
“Hersday Happy Hour”
Discounted cocktails/bottles of wine/dessert & drink pairings
Blackfin
918 Duval St.
4:30-6:30 p.m.
$7 menu
Boathouse Bar and Grill @ Turtle Kraals 🌴🙌🏼🌴
220 Margaret St.
4-6:30 p.m.
Half-price well drinks and beers
Bobby’s Monkey Bar 🌴👩🏻🦰🌴
900 Simonton St.
Noon-8 p.m.
$3 domestic beers / $4 imports / $4 well drinks
(no smoking/vaping, cash only, ATM on site)
Conch Republic Seafood Company (aka “The Conch Farm”) 🌴🙌🏼🌴
631 Greene St.
4-7 p.m.
2-for-1 drink specials
Dante’s 🌴👩🏻🦰🌴
951 Caroline St.
Monday-Friday, 4-8 p.m.
Half-off domestic beers and well drinks / $3.50 Jagermeister and Fireball / $4 Jameson
Geiger Key Marina 🌴👩🏻🦰🌴 / 🌴🚘🌴
5 Geiger Road
4-6 p.m.
Drink specials and special happy hour menu
Green Parrot Bar 🌴👩🏻🦰🌴
601 Whitehead St.
4-7 p.m. Monday-Thursday
4-5:30 p.m. Friday
Discounts on selected drinks and beers
The Grand
314 Duval St.
5-6 p.m.
Half-price appetizers, wine, cocktails and beer
Half Shell Raw Bar 🌴🙌🏼🌴
231 Margaret St.
4:30-6:30 p.m.
2-for-1 drink specials
Hard Rock Café
313 Duval St.
5-7 p.m. and 10 p.m. to closing
Half-price appetizers and drinks
Hogfish Bar and Grill 🌴👩🏻🦰🌴 / 🌴🚘🌴
6810 Front St., Stock Island
4-6 p.m.
Drink specials / happy hour menu
Island Dogs Bar
505 Front St.
4-6:30 p.m. Monday-Friday
Half-price well drinks, bottled beer and wine by the glass / $5.95 menu
Lighthouse Court Hotel Poolside Mojito Bar 🌴👩🏻🦰🌴
902 Whitehead St.
Noon-3 p.m.
$5 Mojitos / $4 Rum Punch / $3 Bud Light Beer
Marriott Beachside 🌴🚘🌴
3841 N. Roosevelt Blvd.
Pool Bar
11 a.m.-1 p.m. and 4-6 p.m. daily
2-for-1 drink specials
Martin’s
917 Duval St.
4-6 p.m.
Half-price drinks and tapas
Mary Ellen’s Bar 🌴🙌🏼🌴
420 Appelrouth Lane
3-6 p.m.
2-for-1 wells and drafts / $5 Jameson / $5 Titos
Old Town Mexican Café
609 Duval St.
4-7 p.m.
Half-price appetizers / Half-price beer, wine and well drinks
Pepe’s
806 Caroline St.
4-6 p.m.
Half-price raw and baked oysters / $6 fresh-squeezed margaritas / Discounted well drinks, beer and wine
The Perry Hotel 🌴👩🏻🦰🌴 / 🌴🚘🌴
7001 Shrimp Road, Stock Island
Salty Oyster Dockside Bar & Grill
4-6 p.m. daily
Half-off premium drinks, house wine, drafts / daily food specials
Matt’s Stock Island Kitchen & Bar
6-8 p.m. daily
$3 specialty drafts / $5 cocktails / 50% off signature wine / $3 oysters / $5 appetizers and crudo
Rams Head Southermost 🌴🙌🏼🌴
804 Whitehead St.
4-6 p.m. Monday-Friday
$5 draft beers, $4 domestic bottles, $2 off wine & liquor + 1/2 price appetizers
The Roost
508 Fleming St.
3-6 p.m.
$10 Stoli Elite martinis
Roostica Pizzeria 🌴👩🏻🦰🌴 / 🌴🚘🌴
5620 MacDonald Ave.
4-6 p.m.
Drink specials and special happy hour menu
Santiago’s Bodega 🌴🙌🏼🌴
207 Petronia St.
3-6 p.m.
Half-price drinks / $5 tapas
Schooner Wharf 🌴👩🏻🦰🌴
202 William St.
8 a.m.- Noon, 5 p.m.-7 p.m.
Half-price alcohol (except during special events)
Sidebar @ Aqua 🌴👩🏻🦰🌴
504 Angela St.
4-8 p.m.
$5 well drinks / $3.75 domestic beers
9 p.m.-late, Mon.-Wed. drink specials
Smokin’ Tuna Saloon 🌴👩🏻🦰🌴
4 Charles St.
3-6 p.m.
Daily drink specials / 2-4-1 premium well drinks
Southernmost Beach Café 🌴👩🏻🦰🌴
1405 Duval St.
Sunday-Thursday
$5 small bites bar menu / $5 draft beer, house wine, well drinks and house margaritas
Southernmost Pint Brewpub
522 Front St.
4-6 p.m.
Daily Happy Hour with 25% off all drinks and discounted appetizers
Square Grouper Bar and Grill and My New Joint 🌴🚘🌴
22658 Overseas Highway, Cudjoe Key
Square Grouper
Tuesday-Saturday
Lunch specials and $7 well drinks
My New Joint
4:30-6:30 p.m.
25% off bottled/canned beer / $1 off draft beer and wine by the glass / $6 cocktail specials daily
Sunset Pier 🌴👩🏻🦰🌴
0 Duval St.
3-6 p.m.
$4 draft beer / $5 glasses of wine and well drinks / $8 frozen drinks
Sunset Tiki Bar @ the Galleon Resort 🌴🙌🏼🌴
617 Front St.
10 a.m.-noon (except Sundays)
2-for-1 bloody marys
4-7 p.m. daily
2-for-1 margaritas or well drinks
Tattoos and Scars 🌴👩🏻🦰🌴
512 Greene St.
Stella on draft $4 all day
Tavern ‘N Town 🌴👩🏻🦰🌴
3841 N. Roosevelt Boulevard
8-11 a.m. daily breakfast happy hour
2-for-1 bloody marys, mimosas, screw drivers
5-7 and 9-11 p.m. 2-for-1 drink specials
Tiki House 🌴👩🏻🦰🌴
430 Greene St.
4-6 p.m.
2-for-1 wells, drafts and zombies
Vinos on Duval 🌴🙌🏼🌴
810 Duval St.
Until 7 p.m. daily – $7 homemade sangrias / $7 winespritzers
Saturday & Sundays – $6 mimosas all weekend
Viva Saloon
903 Duval St.
4-6 p.m.
$3 well drinks / $1 off all beer and house wine / $5 appetizers
The Waterfront Brewery 🌴👩🏻🦰🌴
201 William St.
4-6:30 p.m. daily
All Waterfront Brewery beer and wines by the glass half off
The White Tarpon 🌴🙌🏼🌴
700 Front St.
4-7 p.m.
1/2 off well drinks, wines, beers / $5 margaritas / $5 sangrias / Happy Hour Small Plate Menu
Willie T’s Restaurant and Bar 🌴👩🏻🦰🌴
525 Duval St.
4-7 p.m.
daily drink specials
Yellowfin Bar and Grill @ Oceans Edge Resort and Marina 🌴👩🏻🦰🌴 / 🌴🚘🌴
5950 Peninsular Ave.
3-5 p.m.
specialty drinks / Appetizer Specials
Are you a Key West business that partakes in Happy Hour? Have I missed you in my list? Does your Happy Hour need updating? Contact me here with your Happy Hour deets to be featured!
Sherri in Paradise 