A Guide to the Best Key West Happy Hour Deals

You don’t have to wait till five o’clock in Key West to get the party started! You can find cheap deals on drinks and food at all times throughout the day if you know where to look. Below is a detailed guide to the best Key West happy hour deals around town. But first are a few of our favorites by category. 

Best Place for Seafood Eaters during Happy Hour

Half Shell Raw Bar 

Longest Running Happy Hour

Mary Ellen’s Bar and Restaurant (6 hours) or Bobby’s Monkey Bar (8 hours)

Best Place for Bar Food Apps during Happy Hour

The Commodore’s Boathouse Bar and Grill

Best Place for Domestic Beer Drinkers during Happy Hour

Schooner Wharf Bar

The Place for Live Music during Happy Hour

Hog’s Breath

Best Place for Craft Beer Drinkers during Happy Hour

Waterfront Brewery 

Best Place for Wine Drinkers during Happy Hour

Lucy’s Retired Surfer’s Bar and Restaurant

CONTINUE READING BELOW FOR ALL THE HAPPY HOUR DEALS AROUND KEY WEST

Plan the best Key West bar crawl with this Key West happy hour guide. Where to go for the best seafood, craft beer, wine, and appetizers deals. #keywest #florida #restaurants

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The Best Key West Happy Hour 2019 Guide

Agave 308

If you enjoy Tequila, Agave 308 is where it’s at. You’ll find 100% Blue Agave Tequila drinks made with fresh ingredients in this cozy cantina. 

308 Front Street

Daily 4:30 – 6:30 PM

$6 Margaritas & Discounted Beers

Taco & Tequila Tuesday All Day

Alonzo’s Oyster Bar

Located right on the water just down the boardwalk from Mallory Square, Alonzo’s Oyster Bar offers an array of fresh seafood tapas-style appetizers on special including peel and eat shrimp, coconut shrimp, fried calamari, bang bang shrimp tacos, and raw oysters.

700 Front Street

Daily 4 – 6:30 PM

Half Off Well Drinks, Beer and Wine by the Glass with Discounted Appetizers.

Bagatelle Island Restaurant

Bagatelle Key West Happy Hour is two times a day! Once in the wee hours of the morning when you are nursing that hangover and again later in the day during dinnertime. Located in a beautiful mansion built in 1884 which served as a private home for one hundred years before being turned into a restaurant.

115 Duval Street

Breakfast Daily 9 – 11:30 AM

Discounted Tapas, Small-plate $5 Breakfast Items

Daily 4 – 6:00 PM at the Bar

$5 Tasting Plates and Half Off Most Cocktails

Blue Heaven

Known for its funky backdrop, free spirit ‘tude, and lovely brunch menu, do not dismiss Blue Heaven as a fun spot for happy hour. 

729 Thomas Street

Daily 3:30 – 5:00 PM

Half Price Beer, Wine, Wells, and Selected Specialty Cocktails

Bobby’s Monkey Bar

Local and gay-friendly dive bar off the beaten path with eight hours of Key West happy hour specials. 

900 Simonton Street

Daily 12 – 8:00 PM

$2.50 Domestic and $3.50 Imports and Well Drinks

Charlie Mac’s

A low-key sports bar that offers up barbecue plates smoked to perfection. 

404 Southard Street

2 for 1 Wells, Drafts, Domestics & House Wine

$5 App Menu

Commodore’s Boathouse Bar

Great location on the Harbor with a big selection of appetizers that are half off during Boathouse Key West happy hour. Our favorites are the coconut shrimp, conch fritters, boathouse bread, and filet mignon and mushroom kabobs. 

700 Front Street

Daily 4 – 6:30 PM

Half Off Well Drinks, House Wine, Draft and Craft Beers

50% Small Plates

Plan the best Key West bar crawl with this Key West happy hour guide. Where to go for the best seafood, craft beer, wine, and appetizers deals.
Happy Hour Appetizers at the Boathouse in Key West.

Conch Republic Seafood

No food specials here at the Conch Republic but you will find two-for-one drink specials in an open air venue, patrons swaying to live music and beautiful views of the harbor.

631 Greene Street

Daily 4 – 7:00 PM

2 for 1 Drink Specials on All Beer, Premium Well Drinks, and House Wine in Bar and Patio Only.

FIND SUPER CHEAP KEY WEST

LODGING FOR MILITARY

Cowboy Bill’s Honky Tonk Saloon

It can get a little crazy at Cowboy Bill’s with some mechanical bull riding so call in your inner cowboy or cowgirl and head on over. 

618 Duval Street

Monday – Friday 4 – 7:00 PM

2 for 1 Well Drinks & Domestic Drafts

$2 Tacos Tuesday All Day

Dante’s Restaurant and Pool Bar

Did someone say happy hour menu and a pool bar? Not only can you enjoy cheap food and drink specials but take a swim in their sparkling blue water surrounded by Tiki bars.

951 Caroline Street

Monday – Friday 4:30 – 7:30 PM

Buy One Get One Free Domestic Beers, Well Drinks, Poolside Daydreams, Key West Lemonades, Painkillers, Dark n’ Stormy’s, Fireball, Jameson, Tropikazees & Lemondrops.

And Food Specials include $4 Medium Stone Crab Claws (seasonal), 3 for $2 Peel n Eat Shrimp, $1 Raw Oysters, $5 Wings, Bang Bang Shrimp, Hot Pretzel Bites, Chili Nacho Bowl & Jalapeno Poppers.

Dirty Pig

Smoked barbecue and soulful Blues is the name of the game at Dirty Pig. 

320 Grinnell Street

Daily 4 – 7 PM

Drink Specials 

Daily 10 PM – 2 AM

Drink and $5 Meal Plates

First Flight Island Restaurant & Brewery

There are three reasons to visit First Flight Island Restaurant: it occupies a historic building known as the birthplace of Pan American World Airways, Southernmost Brewery hails from here, and the garden with its towering trees is spectacular.

301 Whitehead Street

Daily 4 -6:00 PM

$3.50 House Craft Brews, Half Off Select Cocktails, and $5 House Wines

$5 Appetizers including Beef Brisket Mac and Cheese, Tuna Poke Wontons, Six Hour Confit Chicken Wings, Hummus Trio with Flatbread, Devil Eggs, and Basket of Fries.

Things to do in Key West - Happy Hour Pub Crawl! After you check out a sunset, find all the best deals on food and drink with our guide.
Happy hour is always a good idea!

General Horseplay

Feeling lucky? Then head over to General Horseplay, a low-key craft cocktail bar, where happy hour depends on the roll of the dice.

423 Caroline Street

3 – 6:00 PM

Roll a 1, your drink (beer, wine or cocktail) is $1; Roll a 2, pay $2; and roll a 3, and pay 1/2 price. Anything else and you are on your own paying full price.

Green Parrot Bar

The Green Parrot is a Key West legendary hangout filled with locals and tourists alike. It’s a no-frills kind of place to throw down a cold one.

601 Whitehead Street

Monday – Thursday 4 – 7:00 PM and Fridays 4 – 5:30 PM

Discounts on Selected Drinks & Beers

The Grand Cafe

Located in the heart of the city on Duval Street, the Grand Key West Happy Hour offers a welcoming wraparound porch, serene garden or indoor Victorian dining room as a backdrop for some wonderful deals.

314 Duval Street

Daily 4 – 7 PM

Half Off Martinis, Wine, Beer, Cocktails 

1/2 Off Apps

Half Shell Raw Bar

No white linen at Half Shell. This casual fish house is a throwback to the old Key West days with some of the freshest seafood on the island.

231 Margaret Street

Daily 4:30 – 6:30 PM

50% Off All Well Drinks, Beers & House Wines

Discounted Seafood Happy Hour Menu including Calamari Rings, Conch Fritters ($5.50), Buffalo Shrimp ($6), Peel and Eat Shrimp ($8.50/$16), Raw Oysters ($5.50/$10), Fish Dip ($5.50), Steam Shrimp ($9/$17.50) & Clams ($10.50), and Clams on the Half Shell ($4.50/$9).

Great happy hour specials at the Commodore's Boathouse in Key West.
Conch Fritters are a must-try in Key West!

Hank’s Hair of the Dog Saloon

Visitors love this place for their outdoor music and friendly vibes. Hit up Garbo’s for some fish tacos next door before or after drinks and you’ll be one happy camper. 

409 Caroline Street

Daily 4 -7 PM

$4 Domestics, $5 Drafts, and $6 Sangrias

Hog’s Breath

The number one place in Key West to listen to live music which happens to roll all day starting at noon.

400 Front Street

Daily 5 – 7:00 PM

Discounts on Well Drinks and Beer

Hurricane Hole Restaurant

The Hole is the perfect outdoor marina and restaurant to visit for a relaxing meal with a great harbor view.

5130 Overseas Hwy 1

4 – 7:00 PM Daily

$3 Domestic Beer, $3 Well Drinks, and $4 House Wines

Discounted appetizers including conch fritters, pulled pork nachos, fish bites, bruschetta, tuna tataki, cheese quesadilla, calamari, and chicken tenders.

Islands Dog Bar

Come as you are and drink what you want at Islands Dog Bar, one of the most dog-loving places in the Keys.

505 Front Street

Monday – Friday 4:30 – 6:30 PM

Half Off Well Drinks, House Wine, and Bottled Domestic Beer

50% Off Raw or Grilled Oysters and Discounted Appetizers including Conch Fritters, Mozzarella Sticks, Buffalo Popcorn Shrimp, Fried Chicken Pot Stickers, and Pizzadillas.

Little Room Jazz Club

Intimate and sophisticated is how I would describe the Little Room Jazz Club and up on stage you’ll find some talented folks jamming away.

821 Duval Street

5:30 – 7:30 PM Daily

1/2 Off Food and Drinks

Lucy’s Retired Surfers Bar & Restaurant

Total laid-back beach vibe with great  Duval Street people watching vantage point.

221 Duval Street

4 – 7:00 PM Daily

$3 Well Drinks, $3 House Wines, and $3 Select Domestics

$5 Appetizers including dip sampling, five chicken wings, loaded fries, two beef tacos, or two BBQ pork sliders.

Mangoes

Lively joint with big outdoor patio and a seafood focused menu.

700 Duval Street

4 PM – 7:00 PM

2 for 1 Cocktails

1/2 Price Starters

Things to do in Key West - Happy Hour Pub Crawl! After you check out a sunset, find all the best deals on food and drink with our guide.
Mangoes on Duval

The Marker 

The Marker is a fresh new hotel on the Historic Seaport and their pool bar, Cero Bodega, offers daily specials dotted with skewers and a few other items.

200 Williams Street

Daily 4 – 7:00 PM

$5 Wells, Drafts and Wines

$5 App Menu with Buy 1, Get 1 Free Pizza

Mary Ellen’s Bar

A friendly neighborhood bar just off Duval Street with one of the longest-running happy hour we could find. Six hours of drinks specials should make any visitor happy.

420 Appelrouth Lane

Monday through Friday, 12 – 6:00 PM, Saturday & Sunday 3 – 6:00 PM

2 for 1 Wine, Well Drinks, Draft Beers, and Draft Cocktails, $5 Jameson and Monkey in Paradise Vodka

$5 Apps including Thai Cucumber Salad, Caesar Salad, Fried Mushrooms, Cheesy Tater Tots, Cup of Tomato Soup with 1/2 Order of Cheesy Garlic Bread or Classic Grilled Cheese.

Mellow Cafe

An off the beaten path craft beer bar that is reminiscent of its namesake: mellow and chill. 

1605 N Roosevelt Street

Monday – Friday 5 – 7 PM

Half Off Drafts, Wine and Sangria

Half Off Starters

Old Town Mexican Cafe

Casual outdoor eatery with a seafood-heavy menu of Mexican plates in tropical-themed digs.

609 Duval Street

Daily 4 – 6:00 PM

1/2 Off Beer, Wine & Well Drinks

1/2 off Appetizers

Old Town Tavern & Beer Garden

The shaded outdoor patio at Old Town Tavern is a perfect spot for people watching on Duval Street. 

900 Duval Street

Daily 4 – 7:00 PM and 11 PM – 1:00 AM

Half Off House Wine and Liquors and 25% off all Beer.

With 50% of Flat Breads and Share Plates.

Things to do in Key West - Happy Hour Pub Crawl! After you check out a sunset, find all the best deals on food and drink with our guide.
Great flatbread and drink specials during happy hour at Old Town.

Pepe’s Cafe

Rustic joint that has been serving up dishes since 1909 making it the oldest restaurant still operating in Key West. It’s almost a rite of passage to eat at Pepe’s so why not come through during happy hour.

806 Caroline Street

4 – 6:00 PM Daily

$5 Margaritas & Discounted Beer, Wine & Well Drinks

Half Price Raw and Baked Oysters

Pinchers

So Pinchers has 2-for-1 drinks all day, every day so we are fans right there. Compound that with the daily seafood specials and it’s a win-win.

712 Duval Street

3 – 6:00 PM Daily

Oysters, Clams, Shrimp, and Wings $0.99 each

Rams Head Southernmost Bar

Just steps away from the party-going Duval Street, Blue Macaw Island Eats and Bar is a tropical oasis with its very own outdoor Tiki bar always hopping with live music.

804 Whitehead Street

Daily 4 – 7:00 PM

$3 Bottled Beer, Well Drinks, and Wines

1/2 Price Appetizers including Buffalo Shrimp, Bruschetta, Baby Back Ribs, Truffle Fries, Chicken Wings, and Lobster Dip.

Rum Row

Located at the Gates Hotel, Rum Row is an outdoor poolside bar well-stocked with rum and cigars alike. 

3824 N Roosevelt

Daily 4 – 7 PM

$3 Domestics, $4 Wells, and $5 House Wines and Selected Crafts

Things to do in Key West - Happy Hour Pub Crawl! After you check out a sunset, find all the best deals on food and drink with our guide.
Waterfront Brewery’s happy hour even applied to flights!

Salute!

Beautiful views at this beachside café right off the sand at Higgs Beach. 

1000 Atlantic Boulevard

Daily 4 – 6 PM

Half Off Drink Specials

Sandbar

Sports bar and live and music at this pub with big lineup of craft beers.

511 Greene Street

Monday – Friday 12 – 4:00 PM 

Midnight – Close

1/2 Price Select Drinks

Santiagos Bodega

Santiago Bodega Key West Happy Hour combines a charming tapas bar with fabulous ambiance. 

Daily 3 – 6:00 PM

Half Price Draft Beers, Wine, Sangria, and Wells

$5 Tapas Menu that Changes Daily

The Schooner Wharf Bar

An outside-only bar with fantastic live music and wharf views. Feels like stepping in to the old Key West times back in the day. 

Daily 7 AM – Noon

Daily 5 – 7:00 PM

$2.00 Draft or Bottle Domestic Beer, $3.00 Well Drinks and Schnapps, $3.25 Imports, $4 House Wine, $5 Bloody Mary’s, $6.00 Premium Wines, and $6.50 Mimosas. 

Shanna Key Irish Pub

An Irish pub is always a good idea for drinks and comfort food. 

1900 Flagler Avenue

Daily 4 – 7:00 PM

$1 or $1.50 Off Drinks

ADD THESE IRISH PUBS

TO YOUR BUCKET LIST

Shots & Giggles

A small local spot half a block off of Duval with a wide selection of craft beers and cocktails.

201 Ann Street

Daily 4 – 7:00 PM

30% Off All Drinks

Smokin’ Tuna Saloon

A mostly outdoor hangout with a courtyard stage and a cool vibe. 

4 Charles Street

Daily 4:30 – 6:30 PM

2 for 1 Beers, Wine and Well Drinks

Discounted Apps

Sunset Pier

THE place to have a drink, sway to live music and watch the sun disappear. Unfortunately, Sunset Pier Key West happy hour is seasonal and only during the summer months.

0 Duval Street

Seasonal 3 – 6:00 PM

$4 Draft Beer, $5 Wine and Well Drinks

Sunset Tiki Bar

A poolside bar overlooking the Gulf of Mexico at The Galleon Resort in Old Town Key West.

617 Front Street

10 AM – 12:00 PM

Two for One Bloody Mary’s

5 PM – 7:00 PM

Two for One Well Drinks, Domestic Beers, and Margaritas

Tattoos and Scars

A local barroom behind Sloppy Joe’s on Greene Street that offers a happy hour and military specials.

512 Greene Street

Daily 4 – 7:00 PM

2 for 1 Domestic Bottles, Drafts and Well Drinks

$3 PBRs

Thirsty Mermaid

If you’re looking for a food-forward locally sourced kind of place then Thirsty Mermaid is your restaurant. And during happy hour, you can sample a few things without breaking the bank.

521 Fleming Street

Daily 4 – 6:00 PM

$2 Pints of Mermaid Lager

$5 Food Plates including Chicken Wings with Chili Pineapple Glaze, Mac and Cheese Croquettes, 1/2 Dozen Apalachicola Oysters, and Ceviche Du Jour.

Toasted Coconut

You’ll find Toasted Coconut poolside at the swanky 24 North Hotel. Grab a drink and settle in for a true holiday experience.

3820 N Roosevelt

Daily 8 – 11:00 AM

$5 Bloodys, Moscow Mules, and Mimosas

Daily 12 – 4:00 PM

$3 Domestics, $4 Wells, $5 Wines and Drafts

Two Friends Restaurant

Two Friends is a casual and down-to-earth spot that has recently won the designation of “Best Bloody Mary” in town. 

512 Front Street

Daily 4 – 7:00 PM

Half Price Appetizers and Drinks

Things to do in Key West - Happy Hour Pub Crawl! After you check out a sunset, find all the best deals on food and drink with our guide.
White Tarpon Happy Hour

Turtle Kraals

A former turtle cannery on the harbor turned bar known for its Caribbean-inspired menu and crazy turtle races.   

231 Margaret Street

Daily 4 – 6:30 PM

Half Off All Beers, Wines, and Well Drinks

App Specials include Potato Skins ($5.99), Wings ($6.50), Guac & Chips, Conch Fritters, Pretzel Bites and Fried Calamari ($6.99), and  Peel and Eat Shrimp ($9/$17)

Viva Saloon

Karaoke, live music and trivia nights in an open patio setting right on Duval. 

903 Duval Street

Daily 4 – 6:00 PM

$3 Well Drinks

$5 Appetizers

Waterfront Brewery

If you are a craft beer drinker like me then you may always look for a brewery on vacation. They don’t often have happy hours so it’s a great find what we have here. Located right in Old Town’s Historic Seaport area you can choose from an array of selections including Southernmost Stout, Lazy Way IPA, Crazy Lady Honey Blonde and many more.

201 Williams Street

Daily 4 – 6:30 PM

Half Price Waterfront Craft Beers, Well Drinks, and Wines by the Glass.

White Tarpon

Tucked away in the corner of the harbor, White Tarpon has outdoor and indoor seating in a low-key setting.

700 Front Street

Daily 4 – 7:00 PM

Half Off Beer, Wine and Wells

$5 Margaritas

App Specials including Onion Rings ($3), Loaded Pub Fries & Pretzels ($5), Chicken Wings & Chicken Nachos ($6), Coconut Shrimp & Smoked Fish Dip ($7), Conch Fritters & Crab Dip ($8), Peel & Eat Shrimp ($9/$14) and Blue Point Oysters ($14)

 

If you have any more places to add to our Key West happy hour list please share in the comments below!

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The best thing to do in Key West includes hitting happy hour! Check out this guide to plan an epic bar crawl with all the special deals. #keywest #bars #thingstodo

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