Famous Bars, Key West
If getting hammered in the Florida heat is your style, you've come to the right place. Key West is home to dozens and dozens of famous and perhaps infamous watering holes. Perhaps the most famous is Sloppy Joe's which used to be a place that Hemingway and his pals hung out. BUT, the Sloppy Joe's where Papa drank at, at first anyway, was a few blocks away from the present location. You see, the original Sloppy Joe's owner was hit with a $1 dollar a week rent increase. Being typical Conch Republic types, he said hell no and closed the bar, moving to another location. During this move is when Hemingway removed a urinal from the old Sloppy Joe's and made it into a cat water fountain at his house. Hemingway was reported to have waxed, "I pissed away so much money in this urinal, I felt like I should bring it home".
By the way, Sloppy Joe's is where they have the annual "Ernest Hemingway Look Alike Contest". I figure most of the contestants are former department store Santas who've gone bad.
Among the other bars, one of particular renown is "The Garden of Eden". It's three floors of increasing hedonism, with the top floor being decorated like a tropical garden. Oh yes, did I mention that the top floor is clothing optional? Now I can't imagine what self-respecting VT member would go on vacation and walk around naked in public...but you never know, right? OK, just to be sure, we didn't. Family trip, folks.
The two most popular activities in Key West are fishing and drinking. Duval Street, which is home to some of Key West's most famous bars, has a guided day tour which takes you to the most famous bars in Key West. To liven up the experience, the tour includes a drink in 5 of these bars.
Most people prefer to do their Key West Pub Crawl in the evening, and without the assistance of a tour guide. We'll talk about those types of pub crawls in the nightlife section.
located on duval street is the 1924 cuban baroque san carlos club. this historic building was the social center for key west's cuban community for decades. at the original san carlos club on this site cuban leader jose marti gave a speech here and also the famous opera star enrico caruso sang here. because of key west's proxminity to cuba the town has always had a vibrant cuban community. in 1883 there were 80 cuban cigar factories in key west. the san carlos club was closed when i was last in key west so i did not have a chance to see the interior. for those interested in cuban culture and history this site is worth checking out.
Stop in to Capt Tony's....and have a Pirate Punch! This is a classic watering hole with over a hundred years of character and charm. This bar has a laid back no-pretense atmosphere marked by the history of Key West as it has evolved around this famed spot. This is where Sloppy Joes was when Hemmingway did most of his work here. For good luck see if you can throw a quarter into the mouth of the big grouper perched on the sign out front. The key is to stand under the sign facing the street and throw the quarter backwards and up to make it in the fishes mouth!
If your accomodation doesn't come equipped with a pool and adjoining tiki bar you may want to visit the pool at Dante's. The bar is located at Key West Bight Marina at the end of Caroline street. Enter from the parking lot or the boardwalk and you'll see their large pool with the distinctive dolphin fountain. It can be a pretty lively place, so we often hang out here instead of the pool at our hotel. The pool is for customers only, so go order a drink and...voila...you're a customer. Cheers.
Sloppy Joes was really busy when I was there in September. It was busy all day everyday. I didn't really hang out there much. I did go to see what all the fuss was about. Guess its okay, but nothing spectacular (at least to me).
Capt Tony's was a great place. The place has tons of character with guests' business cards and underwear located on the walls and rafters throughout the bar. It seems like there was live music there every night.
Glad I could help.
As far as music, there are many bars and pubs with live music. Ricks is an everything venue, I like Hog's Breath and Sloppy Joes, but a bit touristy. But most of it is.
Duval is the main drag but try to discover some of the side streets off the beaten path.
You can rent a car at the airport.
A few years ago in November, my wife and another couple went to Key West and did a Wine and Cheese tasting sailing tour. It was COLD and WET and rough and we ended up as the only ones on the boat, which held about 25 people.
We managed to kill off all the wine and walked off the boat swaying more than we did on the boat! LOL... But we had a great time.
If you head to Miami, remember it is about 120 miles. You can make it in about three hours without stops.
Of course you can always stop at another Key for the night.
There are alot of stops you can make heading out of Key West, so I would plan for the entire day.
In Islamorada there is the Theater of the Sea. Very touristy but we enjoyed it.
Many chances to stop for the required "kitschy" Keys gifts.
Check out the website: http://www.fla-keys.com for info on the Keys.
Let me know if I can be of any further help.
This is a pretty cool bar..its biggest draw is once a year it hosts a rather well attended and prolific Earnest Hemingway look-alike contest. You MUST go here for a minimum of one rum tiki-drink..ITS THE LAW in Key West( would Captain America kid you???)BESIDES...ERNIE would want it that way.
Should stop in the Green Parrot for a bloody mary, they are delicious and garnished with pickled green beans. Stop in for something else if bloody marys aren't your thing. Seems like the times I've been there the locals out number the tourists. Lots of bad/interesting art on the walls. A bit 'divey' but key west has a different measure of dive bar. It's a place I won't skip on any visit to Key West.
This bar was amazing... Historical, to say the least.. Ancient pics everywhere, and even old paintings.. Strange and wierd paintings, but very interesting.. I loved it!!!
When you tire of Duval some of the best bars are down on the Wharf. Music, food, laughter and good drink.
6toejam.com lists all the bars and all the bands in Key West, and it has searchable music schedules.
The 'populated' Sloppy Joe's on the corner is great, but don't miss out on the original Sloppy Joe's, which is a bit smaller and more historical.
This is the actuall bar that Hemmingway spent many hours in. Go there and have a beer and maybe a game of pool and try to catch the atmosphere in the place.