17 Best Key West Happy Hours For 2023
Having lived in Key West for 30-something years, I know a thing or two about happy hour. Friends refer to me as the queen of happy hour because, yeah, I usually keep with all the deals.
While I love a good happy hour, one of my pet peeves is that restaurant happy hour information is often outdated. Guides and customer reviews can be years old.
Sure, restaurants and bars change their offerings over time. That’s why this round-up should be your go-to reliable guide for the best Key West happy hour for the 2023 season.
Deciding Which Key West Happy Hour is Best For You
Landing the best happy hour in Key West depends on a few things: what vibe you’re looking for and what mood you’re in. Some days you want a rockin’ good party with music, other times a cozy craft cocktail suits your mood.
In addition to the details like hours and pricing, this round-up will give you a feel for the experience at each of these places. I’ve personally tipped a beverage at all of them. 😉
1. Alonzo’s Oyster Bar
💃 The Vibe
Located on the Harborwalk with a water view facing the marina, this restaurant has been a long-time reliable spot. Expect a crowd (and a wait) all angling for an outside table. It’s a noisy and lively bag of families, bachelorette groups, couples, and locals.
🍷 The Food & Drink
There’s no guesswork here because there’s actually a happy hour small plate and bar menu. As the name implies, there’s a raw bar offering $2 raw oysters on happy hour. This isn’t gourmet food but decent-portioned bar food and a $4 well drink or glass of wine is a steal in Key West. Happy Hour: 4-6:30 pm
2. Boat House Bar & Grill
💃 The Vibe
If you haven’t been to Key West in a while, you’ll find the Boathouse has moved to a new location. It’s still in the historic Harborwalk area and occupies the space where Turtle Kraals was for so many years.
They have gone all out with a nautical theme and a lot more seating than the prior location. In 2022, it was voted #1 Best Happy Hour in Key West in The Bubba Awards, an annual best-of-contest designated by locals. Go right at 4 pm, otherwise you won’t get a seat.
🍷 The Food & Drink
While you can get the requisite conch fritters, many of the small plates are not run-of-the-mill bar food. Think lobster tempura, bbq ribs, coconut shrimp, baby lamb chops. Pretty nice especially since the food, well drinks, beer, and wine are half-price. HH: 4-6 pm
3. Galleon Sunset Tiki Bar
💃 The Vibe
For me, this is one of the best, laid-back places to enjoy a Key West happy hour AND sunset at the same time. It’s a timeshare/hotel property, located smack downtown, and the tiki bar is perched at the water’s edge. Maneuver your way back there because nothing is visible from the street.
The lounge chairs put you in a perfect position for sunset-watching and, although the chairs are technically for the guests, as long as you’ve bought a drink, no one will run you off. I’ve been doing it for years. Live solo artist music starts at 6.
🍷 The Food & Drink
There’s no food happening here so you’re coming strictly to get hydrated. There’s actually two happy hours. If you want to get an early start, check out the 2 for 1 Bloody Mary’s 10am-Noon, Mon-Sat. Sunset happy hour is 4-7 pm with 2 for 1 rocks margaritas and well drinks.
4. Grand Cafe
💃 The Vibe
You might think this is just a tourist trap given its lower Duval location, but step inside and find the adorable hideaway bar. The historic mansion has lots of old-world charm and the bar is a fav for tourists and locals alike.
If they’re too booked with dinner reservations, snag an outdoor table for the best people-watching Duval St has to offer.
🍷 The Food & Drink
What a great way to sample the fine dining menu with appetizers that are 50% off. Beer, wine, and all cocktails are also half-price. This is one of the more upscale best happy hours in Key West 4-7 pm.
5. Green Parrot
💃 The Vibe
This place opened as a corner grocery store in 1890 and once it turned into a bar, thank goodness, not a thing has changed. My favorite dive bar makes no pretense to be anything other than what it is: a place with great live music and a come-as-you-are attitude. The bar’s motto is “No Sniveling”; need I say more?
Hanging outside on the sidewalk is as much a social scene as being inside. Bands come from throughout Florida, New Orleans and further away, never with a cover charge. There’s a retail store for buying merch as well as a package store.
🍷 The Drink
The only food here is the free popcorn which is always flowing. The very best time to come here is on Fridays for “soundcheck”. The featured band does a set from 5-7 pm and it’s a party not to be missed. Discounted drinks are everyday 4-5:30 pm.
6. Hank’s Hair of the Dog Saloon
💃 The Vibe
This place is pretty much entirely outdoors with free, live music and plenty of seating. Just a few steps off Duval St, it feels a little hidden but it’s loud and lively. Check out the memorial wall of dogs, located inside the building, where patrons have sponsored a plaque to remember their now departed pooch.
🍷 The Food & Drink
Garbo’s Food Truck is permanently parked in the back with a great lineup of eats. Food discounts can be had 4-6 pm and again 10-midnight to quell late-night munchies. There’s two drink happy hours: 11-1 pm grab 50% off Mimosas and Bloody Marys. Come back later from 4-6 pm for $5 well and $8 sangria
7. Little Room Jazz Club
💃 The Vibe
Key West’s only jazz club is oozing with atmosphere. Recently renovated, it has the intimate, clubby feel we all want in a jazz spot. Sit on the front porch for people-watching on Duval St, at the well-appointed bar or at a cozy table.
Happy hour entertainment is at the piano. You will find yourself wanting to linger longer when the live jazz starts at 8 pm with a rotating roster of Key West talent. The local owners are long-time friends of mine so, yes, I’m biased. But if you’re looking for a Key West happy hour spot where you can have conversation, look no further.
🍷 The Food & Drink
There’s a limited and delightful food menu for some early noshing. Craft cocktails and top-shelf liquor are served the proper way-not in plastic! Open Wed-Sunday. Happy Hour is 5:30-7:30 pm.
8. Martin’s
💃 The Vibe
Sampling Martin’s fine dining restaurant is one of the best Key West happy hour deals, if you’re looking for quality tapas. With garden seating in the back, at the bar or tableside on Duval St, this is the place if you’re in the mood for a martini done right. It’s wildly popular so get there by 4 pm or you won’t get a spot.
🍷 The Food & Drink
The tapas here are a cut above the rest. With its German-influenced menu, you’ll find schnitzel strips, bratwurst plus seafood apps you don’t see that often, like scallops florentine, and escargot.
The signature martinis, well drinks, and all the tapas are 50% off. Yes, you read that right. So hurry over there when you get into town for one of the best happy hours in Key West. Happy hour runs from 4-6 pm.
9. Pepe’s Cafe
💃 The Vibe
The atmosphere is old-school Key West. It should be because it’s hailed as the “eldest eating house in the Florida Keys.” The decor is a rustic shipbuilder look just a stone’s throw from the Harborwalk area.
Though it recently changed owners, they haven’t messed with a good thing. Every meal here is home-cooking and the 7-stool outdoor bar has its loyal, local following.
🍷 The Food & Drink
The freshly squeezed grapefruit, orange, and lime juices are what make the cocktails stand out. A $6 margarita and half-price well drinks (and it’s a premium well) are what you should be ordering here. That, plus the half-price raw oysters (the baked ones are yummy too but not on discount) creates the quintessential flip-flop Keys experience. HH: 4-6 pm
10. Ram’s Head
💃 The Vibe
I think of this place as the gateway to Bahama Village, a part of Key West that has thrived over recent years. It’s a casual, outdoor spot always with live music during HH. There’s some limited parking out back (unheard of in this part of town) and some cornhole games set up.
🍷 The Food & Drink
I’d call the eats basic bar food, peel n’ eat shrimp which is a good deal at 50% off for any app. Table or bar seating is available and it’s one of the cheaper places in town especially if you’re a beer drinker; $4 draft or domestic bottles and $2 off any wine or liquor. HH: 4-6 pm
11. Roostica
💃 The Vibe
Located on Stock Island just 10 minutes from downtown Key West, this pizzeria has a very authentic Italian feel. The owners are long-time local restauranteurs and know what they’re doing. The wood-fired ovens, high-top tables, a lively bar, and outdoor picnic table-style seating offers variety for everyone.
🍷 The Food & Drink
This is where you come for wood-fired pizza and other small Italian specialty plates. There’s a $5 small plate menu with bruschetta, wood-fired wings, sausage and meatball sliders, and a 1-topping mini-pizza. The happy hour bar menu includes $7 wine, $4 well and beers for $4 and $3, draft and domestic respectively and runs from 4-6 pm.
12. Santiago’s Bodega
💃 The Vibe
Nestled deep in the Bahama Village area, this Spanish tapas restaurant has a charming atmosphere. It can be loud later in the evening, but happy hour is usually still on the quiet side. An outdoor table is also an option. Don’t show up without a reservation for one of the best happy hours in Key West.
🍷 The Food & Drink
If you’re a lover of small plates as I am, then you’re like this place. There’s a $5 tapas menu that changes daily though you can also order off the regular tapas menu. The name of the game is sharing so go hungry or go with friends.
It’s beer, wine, and sangria only, all priced at 50% off. This, too, is one of the best happy hours in Key West for quality, interesting tapas. Get here between 3-6pm.
13. Southernmost Beach Cafe
💃 The Vibe
This is as close as you’ll get to having your toes in the sand while sipping a cocktail. This really is a beach bar so show up in your bathing suit or nothing more serious than a pair of shorts.
🍷 The Food & Drink
Appetizers are all 50% off and offer a good selection of bar bites. Combine that with the $5 drink specials like 20 oz drafts, well drinks and house wine and you’ve saved some serious money. Money you can spend on that new bathing suit! Happy hour is 4-6 pm.
14. The Roost
💃 The Vibe
This tiny speck of a bar is perfect if you’re looking for craft cocktails in a dark, sexy setting before the sun goes down. It’s a cool little spot with a liquor store as, sort of, part of the bar.
🍷 The Food & Drink
Signature cocktails is their thing and if you show up during HH you’ll find $10 Stoli martinis and cosmos, $6 tap cocktails, $8 wine, and 1/2 price caviar. A charcuterie board and other nibbles go well with the fancy pants drinks. If you’re into day drinking, this works well because happy hour runs from noon-6 pm.
15. The Saint
💃 The Vibe
This boutique hotel lobby and bar makes me feel like I left Key West and ended up in art deco South Beach, Miami. The ambiance is whimsical and the bar serves up some of the best craft cocktails in town to make this hidden gem one of the best happy hours in Key West.
🍷 The Food & Drink
There’s an assortment of $10 plates that go nicely with the upscale drinks. Beverages are 30% off and although this is not a bargain place, it is a bargain for the uniqueness and quality of what they put across the bar. And it has the quirkiest happy hour which is actually easy to remember, 4:17-7:17 pm.
16. Vino’s Wine Bar
💃 The Vibe
Wine bars are for conversation and people-watching and you’ll get both here. There’s always someone new to chat with at the bar or enjoy the Duval St view from the porch.
🍷 The Food & Drink
It’s not that there’s a lot on HH special here, but you can nurse any glass of wine and enjoy the atmosphere. Charcuterie boards are always available, Sundays are $5 mimosas, and $7 homemade sangria is every day until 7 pm.
17. Viv’s Wine Bistro
💃 The Vibe
Take a trip to France while still in Bahama Village at this uber-cute, tiny wine spot. There’s retail wines and cheeses to buy in addition to enjoying both at the few street-side tables or indoors.
These are not rock-bottom prices, but you get what you pay for here. The same owners operate The Creperie, immediately next store, so it’s a whole lot of French going on.
🍷 The Food & Drink
The menu is more extensive than you expect, from raclettes to duck salad. The happy hour deal is 50% off a glass of red or white wine and domestic beer when ordering any food or cheese plate until 6 pm.
Wrap Up: Finding the Best Key West Happy Hours
So many places to go and only so much time to make it happen! Decide what you’re in the mood for then pick your spot accordingly. I’ve taste-tested every one of these places, and I’m sure you’re going to love all of them.
Restaurants and bars are known to change service hours (especially when short-staffed) so it’s always a good idea to call ahead and confirm their happy hour deals.
Key West has a lot to offer visitors, and there’s no doubt that hitting up a good happy hour is one of the best!
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