By Kevin Wilkerson, PubClub.com Nightlife Blogger
In the PubClub.com series of “simple guides” to cities and party places around the world, Key West might be the simplest of them all.
That’s because all you need to do is stick with a few basics, be at them at the right time and fill things in from there. But that would not make for much of an article so do add some depth to it, I am also providing some of my experiences in these and couple of other places.
First, though, the “routine.”
• Sunsets at Mallory Square. This is a daily must ritual when in Key West.
• Sloppy Joe’s. For you day drinkers, this is a place to start and return during often during your time in Key West.
• Captain Tony’s Saloon. It’s dark and well worn but due to it’s famous assocation with former resident Jimmy Buffett it’s worth having a beer (or two) in and it still gets in a few characters. While you’re at it you might as well have a beer or a stiff one at Chart House. That’s where Jerry Jeff Walker took Jimmy Buffett to when he first showed him Key West and where Buffett first played “Margaritaville.”
• Tree Bar. This small outdoor bar at the base of Duval Street is one of my favorite places in the Conch Republic. For one thing, it got on my good side when the bartender used freshly-squeezed orange juice to put into my rum drink. It’s a kicked-back, casual place that’s good anytime after sunset. In fact, I recommend it as your first post-Mallory Square sunset bar. It’s also gets good walk-through traffic so it’s a pretty easy place to meet people.
• Rick’s Bar. Okay, this is a bit broad because Rick’s owns nine Key West bars, including the aforementioned Tree Bar. I prefer the upstairs bar, which is a dance club and downstairs for live music. The latter can get pretty lively with a fun party crowd, especially for karaoke, which is Midnight-4 a.m.
• Kevin’s Irish Bar. This is a later-night place and I don’t have it here just because of the name. I am NOT involved in it, by the way.
Other bars of interest: Margaritaville, of course, tho it can be touristy (and by that I mean calm) but I always poke my head in there to see if I like the band. Schooner Wharf Bar. I go there in the afternoon between lunch and the sunset on Mallory Square. There’s always a guy with a guitar playing and it’s often someone who has been there for decades. It’s also on the marina so the view of the boats is nice.
I kind of have a fond place in my heart for Schooner Wharf, for it was the 11th – and final – bar I made it to during a 12-bar Key West St. Patrick’s Day pub crawl. I had gone there with my friend Hayney from West Palm Beach, who knows Key West the way I know the inside of a beer bottle. I simply could not make it to the final bar because I was out very late the previous evening and did not get back to the hotel until the sun was coming up on the pub crawl day.
Mallory Square was introduced to me by Hayney but I knew it was THE thing do do in Key West from the person who introduced me to Hayney, Laz. A co-worker at the PR agency I where I was employed at the time, Laz insisted that I do those sunsets nightly. I’m glad I did, too, because it really sets the tone for a good time in Key West. There are street performers – really good ones, too – who juggle sticks of fire while balancing on a tall unicycle and all sort of other creative acts. Plus, there’s the sunset.
Laz knew I was under good guidance with Hayney and he introduced me to Sloppy Joe’s and Captain Tony’s Saloon. One time, a friend was in Key West the same time as Hemingway Days. Sloppy Joe’s is the headquarters for that quirkly event and it even holds an Ernest Hemingway look-alike contest as part of it.
What I found out most about Key West in my first visit was that you just kind of wander around, up and down Duval Street, going in and out of the seemingly endless t-shirt shops, make you way to the Southernmost Point buoy and eventually sit down somewhere for a drink.
And that really is a simple guide to Key West.
Key West Bars Q&A
What street has the best nightlife in Key West?
Duval Street is the center of Key West nightlife, with bars, live music and restaurants.
What is the most famous bar in Key West?
Sloppy Joe’s is the island’s best-known bar, followed closely by Captain Tony’s Saloon, Hog’s Breath Saloon and Green Parrot.
Does Key West have live music every night?
Yes. Live music starts in the afternoon and continues until late at night throughout Duval Street and surrounding bars.
What is the best time to go out in Key West?
Happy hour begins around 4 p.m., but many visitors start bar hopping during the afternoon and stay out well into the evening.
Can you walk between Key West bars?
Yes. Most of the famous bars are within a few blocks of each other, making Key West one of America’s best walkable nightlife destinations.
Looking for detailed reviews of every bar? Read PubClub’s Ultimate Key West Bar Guide.
Kevin Wilkerson is the founder of PubClub.com, an award-winning journalist and nightlife expert who has covered destinations, events and entertainment for more than two decades, including Key West. While working as a newspaper reporter, he received an Associated Press award for investigative journalism.
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