There’s no place like Key West to drown your sorrows. Unfortunately, Key West bars are known for many things, but being a great value is not one of those things. It’s very easy to blow through your cash on this rock.
Enter the partly mythical, sometimes elusive, but always tempting Key West happy hour. Is it possible to find deals on this island? Is it possible to get very drunk while attempting to find said deals? What if you’ve got the munchies — is there a cure for that?
For answers to these questions and many more, let’s dive into the nitty gritty and find the best happy hour in Key West.
Finding True Happiness
Keep in mind that Key West bars and restaurants do not limit themselves when it comes to happy hours. Where most towns have a 4–6 p.m. happy hour, Key West happy hour times may be organized any which way. Some have morning happy hours; others have late-night happy hours. There are so many to pick from that you can probably find a place to make it happier no matter what hour it is.
And think about what you actually want in your happy hour. Happiness is a state of mind, but most places try to encourage it with discounts on drinks, food, or both. Seek out the happy hour that will make you the happiest: are you hungry or thirsty?
And then, really explore your inner happiness. What makes you happier: beer, martinis, or margaritas? Well drinks? Disgusting White Claws? As the saying goes, there are as many fetishes as there are fetishers… or something like that.
Finding the Happiest Key West Happy Hour
The brutal truth, since you’re still sober, is that I don’t know where the best happy hour is right now. Key West bars and restaurants are like the shifting sands at the Key West sandbars. They come and go, menu offerings change, and happy hours turn sad. So it’s impossible to keep any list updated with all the changes going on.
So, what’s a visitor to do? The best I can offer is a little advice and some starting point. Below is a list of popular and well-known spots that offer authentic Key West happy hour discounts. But I can’t promise they’re still around or still offering these prices by the time you read this.
Probably the most-talked-about and best-known Key West happy hour is over at The Boat House. Considering how it is talked about and well known, expect it to be crowded!
The Boat House has won the local Keys Weekly People’s Choice BUBBA Award three years in a row for best happy hour, so it’s on everyone’s list for a reason. It goes from 4–6:30 p.m. every day and includes half off all small plates, well drinks, wine, and draft and craft beers. Not too shabby. Half price makes it a great time to try some of the best conch fritters in Key West.
Martin’s is a fancy — exactly the opposite of The Boat House, actually. But if you’re looking for happy hour with a touch of class, this steak and lobster hotspot is worth a shot.
Happy hour at Martin’s is from 4–6 p.m. every day except on holidays. It’s the place for half off their delicious tapas and martinis. Get me the shrimp and scallop skewer and a Bombay martini, please.
Old Town Tavern is home to twice-daily happy hours: from 4–7 p.m. and again from 11 p.m. to 1 a.m. That’s a lot of happiness to fit into one day! You get 50 percent off wine, house liquor, share plates, and flatbreads, plus 25 percent off all beer.
You might also want to check out Whiskey Wednesdays if you’re into that sort of thing. Half off whiskey, scotch, and bourbon every Wednesday from 9 p.m. to closing.
You may know this little spot as one of the best places to watch the sunset in Key West, but it’s also got some great happy hour choices. The Sunset Tiki is located right on Key West harbor, just north of Mallory Square.
Almost every day (just not on Sundays), they offer two happy hours: one morning and one evening. From 10 a.m. to noon, Monday through Saturday, they offer 2-for-1 Bloody Marys. Evening happy hour is from 4 to 7 p.m., seven days a week, and includes 2-for-1 margaritas on the rocks or well drinks.
Getting Happier at Key West Happy Hour
Key West is a pretty happy place, with plenty of happy hours to go around. If you’re bored of the same old options, hit up the ol’ Google and see what the locals are discussing. There’s an excellent thread over on Tripadvisor where someone who likes to drink and eat a lot has listed them all. There’s also a local guy who is all up on his TikTok; check it out @mrhappyhourkeywest.
