🍹 TIPSY’S GUIDE TO KEY WEST HAPPY HOUR
Because Full Price is Highly Overrated
Key West takes Happy Hour seriously. Very seriously.
From half-price oysters overlooking the marina to craft cocktails, 2-for-1 drinks and late-night specials on Duval, Happy Hour around here is practically an island sport.
Whether you’re looking for a cold beer after a day on the water, oysters before dinner, a sunset cocktail or somewhere to start a night you may or may not remember, we’ve rounded up some of our favorite Key West Happy Hours.
Drink something cold. Eat something delicious. Save a few bucks. Keep It Tipsy. 🦜
🌴 WALK FROM THE TIPSY PARROT
No Car. No Uber. No Problem.
One of the best things about staying at The Tipsy Parrot is having some of Key West’s best food, drinks and Happy Hours right outside your door.
🍷 Santiago’s Bodega
207 Petronia Street
Happy Hour: Daily 3–6 PM
Half-price draft beer, wine and sangria by the glass, plus a rotating selection of discounted tapas.
Tucked right here in Bahama Village, Santiago’s is one of our favorite ways to turn Happy Hour into dinner.
Visit Santiago’s Bodega
🦜 TIPSY SAYS: Order a few tapas. Then a few more. Congratulations, you accidentally had dinner.
🍺 Green Parrot Bar
601 Whitehead Street
One of Key West’s legendary watering holes and practically a neighbor of The Tipsy Parrot. Come for a cold drink and stay for the live music, characters and unmistakable old-Key-West atmosphere.
Visit Green Parrot Bar
🦜 TIPSY SAYS: If you’re staying this close to the Green Parrot and never go inside, we need to talk.
🌮 Old Town Mexican Café
609 Duval Street
A tropical courtyard right on Duval with Mexican food, margaritas and afternoon Happy Hour specials. An easy stop before heading farther down Duval for the evening.
🍸 Martin’s Key West
917 Duval Street
Happy Hour: Daily 5–6 PM & Late Night 9:30–10:30 PM
A more polished Upper Duval Happy Hour featuring discounted tapas and signature martinis. And yes, they have a second late-night Happy Hour.
Visit Martin’s Key West
🦜 TIPSY SAYS: Two Happy Hours in one day. Finally, someone understands vacation.
🍹 Rams Head Southernmost
804 Whitehead Street
Happy Hour: Currently 4–6 PM
A relaxed tropical setting close to the house with food, cocktails and live entertainment.
Visit Rams Head Southernmost
🤪 Mary Ellen’s Bar & Kitchen
420 Appelrouth Lane
Quirky, irreverent and very Key West. Mary Ellen’s offers weekday Happy Hour specials along with food, drinks, games and some wonderfully unusual events.
🦜 TIPSY SAYS: Things have a tendency to get weird here. We consider that a feature.
🦪 EAT YOUR WAY THROUGH HAPPY HOUR
Oysters • Seafood • Small Plates • “I Guess This Is Dinner”
Some Happy Hours are about cheap drinks. These are about strategically replacing dinner with appetizers.
🦪 Half Shell Raw Bar
231 Margaret Street
Happy Hour: Daily 4:30–6:30 PM
One of Key West’s strongest food Happy Hours. Current specials include discounted starters and raw-bar selections, including oyster specials, along with discounted wells, house wine and beer.
🦜 TIPSY SAYS: Oysters overlooking the marina at Happy Hour prices. Math has finally become useful.
🦪 Alonzo’s Oyster Bar
700 Front Street
Happy Hour: Daily 4–6 PM
Waterfront Happy Hour overlooking A&B Marina with half-price small plates and a daily oyster special.
🦐 Pepe’s Café
806 Caroline Street
One of Key West’s oldest restaurants and a wonderfully old-school place for an afternoon drink and seafood. Current Happy Hour offerings include discounted drinks and seafood selections such as Key West pink shrimp and oysters.
🦜 TIPSY SAYS: Old Key West. Cold drinks. Pink shrimp. Don’t overcomplicate this.
🍽️ The Boat House
Historic Harbor Walk
The Boat House has long been known for one of the island’s more aggressive Happy Hour deals, with discounts on both drinks and small plates.
Visit The Boat House
⛵ HAPPY HOUR WITH A VIEW
Boats • Harbor Views • Sunsets • Flip-Flops
If we’re going to have a drink, we might as well have something pretty to look at.
⚓ Schooner Wharf Bar
202 William Street
An open-air Historic Seaport institution surrounded by sailboats, working boats and live music.
It’s one of those places where Happy Hour can quietly become sunset, which can quietly become “Should we order another round?”
🦜 TIPSY SAYS: Boats in front of you. Cold drink beside you. Whatever was on today’s schedule can wait.
🦐 Conch Republic Seafood Company
631 Greene Street
Happy Hour: Daily 4–7 PM
A long waterfront Happy Hour at the Historic Seaport with drink specials and plenty of Key West atmosphere.
Visit Conch Republic Seafood Company
🍺 Waterfront Brewery
201 William Street
House-brewed beer, food and a waterfront location right in the Historic Seaport.
🌅 Sunset Tiki Bar at the Galleon
617 Front Street
This one earns its place on the list largely because of the setting. Grab a drink, find a seat near the water and watch Key West do its sunset thing.
🦜 TIPSY SAYS: If your Happy Hour comes with a sunset, technically you’re multitasking.
🍸 COCKTAILS & DATE NIGHT
Martinis • Craft Cocktails • Small Plates • Slightly More Civilized
Sometimes Tipsy puts on a collared shirt.
🍸 The Roost
508 Fleming Street
Happy Hour: Currently Daily 12–6 PM
An intimate cocktail bar known for properly made drinks and an unusually civilized Happy Hour, including featured cocktails and food specials.
Visit The Roost
🦜 TIPSY SAYS: Half-price caviar and cocktails before dinner. Look at us being fancy.
🎲 General Horseplay
423 Caroline Street
Creative cocktails, great bartenders and enough personality to keep things from becoming too sophisticated.
🍸 Martin’s Key West
917 Duval Street
Martinis, tapas and a polished Upper Duval atmosphere make this one of our favorite date-night Happy Hour options.
Visit Martin’s Key West
🥂 Bagatelle
115 Duval Street
A beautiful historic house on Duval with one particularly Key West feature: a morning Hangover Happy Hour, along with afternoon specials.
🦜 TIPSY SAYS: A morning Happy Hour has a completely different name where we come from. But we’re going with it.
🍺 COLD BEER & CASUAL
No Reservations • No Fancy Shoes • No Problem
Sometimes you don’t need a craft cocktail involving smoke and rosemary. You need a cold beer.
🍺 First Flight Island Restaurant & Brewery
301 Whitehead Street
House-brewed beer inside one of Key West’s historic buildings, with a relaxing courtyard and afternoon Happy Hour.
Visit First Flight
🦜 Green Parrot Bar
601 Whitehead Street
Live music, cold drinks and zero need to dress up.
Visit Green Parrot Bar
🐕 Hank’s Hair of the Dog Saloon
409 Caroline Street
Daytime drink specials, live music and exactly the kind of name you’d expect from a Key West bar.
🍹 Tiki House
203 Duval Street
Happy Hour: Currently Daily 12–3 PM
Tropical drinks right on Duval, with current Happy Hour specials including discounted wells, beer and Zombies.
Visit Tiki House Key West
🦜 TIPSY SAYS: If your cocktail is called a Zombie and Happy Hour starts at noon, the warning signs were clearly posted.
🌅 DAY DRINKING STARTS EARLY
Because Waiting Until 5 PM Seems Arbitrary
Key West has apparently decided that the words “Happy Hour” describe a state of mind rather than an actual hour.
🥂 Bagatelle — Morning Hangover Happy Hour
🍹 Tiki House — Happy Hour starting around noon
🍸 The Roost — Current specials beginning around noon
🐕 Hank’s Hair of the Dog — Daytime drink specials
⚓ Schooner Wharf — Historically known for both morning and afternoon Happy Hours
🦜 TIPSY SAYS: Somewhere it’s five o’clock. Key West apparently stopped caring where.
🌙 THE SECOND HAPPY HOUR
Because Apparently One Wasn’t Enough
Missed Happy Hour because you were at the beach? Key West has thoughtfully provided a loophole.
🍸 Martin’s Key West
917 Duval Street
Late Happy Hour: 9:30–10:30 PM
A second round of Happy Hour specials later in the evening.
Visit Martin’s Key West
🍺 Old Town Tavern
900 Duval Street
Known for both afternoon and late-night Happy Hour periods, making it a particularly useful stop after wandering Duval.
Visit Old Town Tavern
🦜 TIPSY SAYS: You missed Happy Hour? Key West has reviewed your appeal.
🦜 TIPSY’S QUICK PICKS
🦪 OYSTERS & SEAFOOD — Half Shell Raw Bar or Alonzo’s
⛵ WATERFRONT — Schooner Wharf or Conch Republic
🌴 WALK FROM THE PARROT — Santiago’s Bodega or Green Parrot
🍸 DATE NIGHT — Martin’s or The Roost
🍺 COLD BEER & LIVE MUSIC — Green Parrot or Hank’s
🌅 START EARLY — Bagatelle or Tiki House
🌙 LATE-NIGHT HAPPY HOUR — Martin’s or Old Town Tavern
🤷 I HAVE NO IDEA — Walk toward Duval. You’ll figure it out.
🍹 ONE IMPORTANT ISLAND RULE
Happy Hour Happens on Island Time
Happy Hour schedules, menus and specials change frequently. We do our best to keep this guide current, but always check the bar or restaurant’s website before heading out for the latest times and specials.
🦜 And if the deal changed, don’t blame Tipsy. He’s a parrot. He doesn’t even carry a wallet.